diff --git a/apps/sim/tools/clerk/add_organization_member.ts b/apps/sim/tools/clerk/add_organization_member.ts
index fdf55734496..d444d627003 100644
--- a/apps/sim/tools/clerk/add_organization_member.ts
+++ b/apps/sim/tools/clerk/add_organization_member.ts
@@ -6,6 +6,7 @@ import type {
   ClerkOrganizationMembership,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkAddOrganizationMember')
 
@@ -47,7 +48,7 @@ export const clerkAddOrganizationMemberTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}/memberships`,
+      `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}/memberships`,
     method: 'POST',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/ban_user.ts b/apps/sim/tools/clerk/ban_user.ts
index be902a68758..5717c3f90e7 100644
--- a/apps/sim/tools/clerk/ban_user.ts
+++ b/apps/sim/tools/clerk/ban_user.ts
@@ -6,6 +6,7 @@ import type {
   ClerkUser,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkBanUser')
 
@@ -31,7 +32,8 @@ export const clerkBanUserTool: ToolConfig<ClerkBanUserParams, ClerkBanUserRespon
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/users/${params.userId?.trim()}/ban`,
+    url: (params) =>
+      `https://api.clerk.com/v1/users/${safeUrlPathSegment(params.userId, 'userId')}/ban`,
     method: 'POST',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/create_organization_invitation.ts b/apps/sim/tools/clerk/create_organization_invitation.ts
index cc33019257c..78f45b4726d 100644
--- a/apps/sim/tools/clerk/create_organization_invitation.ts
+++ b/apps/sim/tools/clerk/create_organization_invitation.ts
@@ -6,6 +6,7 @@ import type {
   ClerkOrganizationInvitation,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkCreateOrganizationInvitation')
 
@@ -83,7 +84,7 @@ export const clerkCreateOrganizationInvitationTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}/invitations`,
+      `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}/invitations`,
     method: 'POST',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/delete_allowlist_identifier.ts b/apps/sim/tools/clerk/delete_allowlist_identifier.ts
index a23606557b5..d16f9b11fc2 100644
--- a/apps/sim/tools/clerk/delete_allowlist_identifier.ts
+++ b/apps/sim/tools/clerk/delete_allowlist_identifier.ts
@@ -6,6 +6,7 @@ import type {
   ClerkDeleteResponse,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkDeleteAllowlistIdentifier')
 
@@ -35,7 +36,7 @@ export const clerkDeleteAllowlistIdentifierTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.clerk.com/v1/allowlist_identifiers/${params.identifierId?.trim()}`,
+      `https://api.clerk.com/v1/allowlist_identifiers/${safeUrlPathSegment(params.identifierId, 'identifierId')}`,
     method: 'DELETE',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/delete_blocklist_identifier.ts b/apps/sim/tools/clerk/delete_blocklist_identifier.ts
index a915de0e6d1..4935ba53767 100644
--- a/apps/sim/tools/clerk/delete_blocklist_identifier.ts
+++ b/apps/sim/tools/clerk/delete_blocklist_identifier.ts
@@ -6,6 +6,7 @@ import type {
   ClerkDeleteResponse,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkDeleteBlocklistIdentifier')
 
@@ -35,7 +36,7 @@ export const clerkDeleteBlocklistIdentifierTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.clerk.com/v1/blocklist_identifiers/${params.identifierId?.trim()}`,
+      `https://api.clerk.com/v1/blocklist_identifiers/${safeUrlPathSegment(params.identifierId, 'identifierId')}`,
     method: 'DELETE',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/delete_organization.ts b/apps/sim/tools/clerk/delete_organization.ts
index e14aaca1b40..5b6597a4193 100644
--- a/apps/sim/tools/clerk/delete_organization.ts
+++ b/apps/sim/tools/clerk/delete_organization.ts
@@ -6,6 +6,7 @@ import type {
   ClerkDeleteResponse,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkDeleteOrganization')
 
@@ -34,7 +35,8 @@ export const clerkDeleteOrganizationTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}`,
+    url: (params) =>
+      `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}`,
     method: 'DELETE',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/delete_user.ts b/apps/sim/tools/clerk/delete_user.ts
index 94fe3fe992d..67de1da8ea3 100644
--- a/apps/sim/tools/clerk/delete_user.ts
+++ b/apps/sim/tools/clerk/delete_user.ts
@@ -6,6 +6,7 @@ import type {
   ClerkDeleteUserResponse,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkDeleteUser')
 
@@ -31,7 +32,8 @@ export const clerkDeleteUserTool: ToolConfig<ClerkDeleteUserParams, ClerkDeleteU
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/users/${params.userId?.trim()}`,
+    url: (params) =>
+      `https://api.clerk.com/v1/users/${safeUrlPathSegment(params.userId, 'userId')}`,
     method: 'DELETE',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/get_jwt_template.ts b/apps/sim/tools/clerk/get_jwt_template.ts
index 311e21aa61e..49a66e0b6ad 100644
--- a/apps/sim/tools/clerk/get_jwt_template.ts
+++ b/apps/sim/tools/clerk/get_jwt_template.ts
@@ -6,6 +6,7 @@ import type {
   ClerkJwtTemplate,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkGetJwtTemplate')
 
@@ -34,7 +35,8 @@ export const clerkGetJwtTemplateTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/jwt_templates/${params.templateId?.trim()}`,
+    url: (params) =>
+      `https://api.clerk.com/v1/jwt_templates/${safeUrlPathSegment(params.templateId, 'templateId')}`,
     method: 'GET',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/get_organization.ts b/apps/sim/tools/clerk/get_organization.ts
index 14b3f1a6ffb..88d4e51c0f2 100644
--- a/apps/sim/tools/clerk/get_organization.ts
+++ b/apps/sim/tools/clerk/get_organization.ts
@@ -6,6 +6,7 @@ import type {
   ClerkOrganization,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkGetOrganization')
 
@@ -35,7 +36,8 @@ export const clerkGetOrganizationTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}`,
+    url: (params) =>
+      `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}`,
     method: 'GET',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/get_session.ts b/apps/sim/tools/clerk/get_session.ts
index ed271e09d16..066bfb1ec91 100644
--- a/apps/sim/tools/clerk/get_session.ts
+++ b/apps/sim/tools/clerk/get_session.ts
@@ -6,6 +6,7 @@ import type {
   ClerkSession,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkGetSession')
 
@@ -31,7 +32,8 @@ export const clerkGetSessionTool: ToolConfig<ClerkGetSessionParams, ClerkGetSess
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/sessions/${params.sessionId?.trim()}`,
+    url: (params) =>
+      `https://api.clerk.com/v1/sessions/${safeUrlPathSegment(params.sessionId, 'sessionId')}`,
     method: 'GET',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/get_user.ts b/apps/sim/tools/clerk/get_user.ts
index d956509767c..f8469d1e835 100644
--- a/apps/sim/tools/clerk/get_user.ts
+++ b/apps/sim/tools/clerk/get_user.ts
@@ -8,6 +8,7 @@ import type {
   ClerkUser,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkGetUser')
 
@@ -33,7 +34,8 @@ export const clerkGetUserTool: ToolConfig<ClerkGetUserParams, ClerkGetUserRespon
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/users/${params.userId?.trim()}`,
+    url: (params) =>
+      `https://api.clerk.com/v1/users/${safeUrlPathSegment(params.userId, 'userId')}`,
     method: 'GET',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/get_user_oauth_token.ts b/apps/sim/tools/clerk/get_user_oauth_token.ts
index 2c6e8602f8f..8032c3dad8f 100644
--- a/apps/sim/tools/clerk/get_user_oauth_token.ts
+++ b/apps/sim/tools/clerk/get_user_oauth_token.ts
@@ -6,6 +6,7 @@ import type {
   ClerkOAuthAccessToken,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkGetUserOauthToken')
 
@@ -43,8 +44,8 @@ export const clerkGetUserOauthTokenTool: ToolConfig<
 
   request: {
     url: (params) => {
-      const providerSlug = params.provider?.trim().replace(/^oauth_/, '')
-      return `https://api.clerk.com/v1/users/${params.userId?.trim()}/oauth_access_tokens/oauth_${providerSlug}`
+      const providerSlug = safeUrlPathSegment(params.provider, 'provider').replace(/^oauth_/, '')
+      return `https://api.clerk.com/v1/users/${safeUrlPathSegment(params.userId, 'userId')}/oauth_access_tokens/oauth_${providerSlug}`
     },
     method: 'GET',
     headers: (params) => {
diff --git a/apps/sim/tools/clerk/list_organization_invitations.ts b/apps/sim/tools/clerk/list_organization_invitations.ts
index 9aa02429a45..d1f0bf72c1e 100644
--- a/apps/sim/tools/clerk/list_organization_invitations.ts
+++ b/apps/sim/tools/clerk/list_organization_invitations.ts
@@ -6,6 +6,7 @@ import type {
   ClerkOrganizationInvitation,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkListOrganizationInvitations')
 
@@ -74,7 +75,7 @@ export const clerkListOrganizationInvitationsTool: ToolConfig<
       if (params.offset) queryParams.append('offset', params.offset.toString())
 
       const queryString = queryParams.toString()
-      const base = `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}/invitations`
+      const base = `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}/invitations`
       return queryString ? `${base}?${queryString}` : base
     },
     method: 'GET',
diff --git a/apps/sim/tools/clerk/list_organization_memberships.ts b/apps/sim/tools/clerk/list_organization_memberships.ts
index 5c1bac5f3b9..643c21aef00 100644
--- a/apps/sim/tools/clerk/list_organization_memberships.ts
+++ b/apps/sim/tools/clerk/list_organization_memberships.ts
@@ -6,6 +6,7 @@ import type {
   ClerkOrganizationMembership,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkListOrganizationMemberships')
 
@@ -71,7 +72,7 @@ export const clerkListOrganizationMembershipsTool: ToolConfig<
       }
 
       const queryString = queryParams.toString()
-      const base = `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}/memberships`
+      const base = `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}/memberships`
       return queryString ? `${base}?${queryString}` : base
     },
     method: 'GET',
diff --git a/apps/sim/tools/clerk/lock_user.ts b/apps/sim/tools/clerk/lock_user.ts
index 290cbc496e4..abc96beb072 100644
--- a/apps/sim/tools/clerk/lock_user.ts
+++ b/apps/sim/tools/clerk/lock_user.ts
@@ -6,6 +6,7 @@ import type {
   ClerkUser,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkLockUser')
 
@@ -31,7 +32,8 @@ export const clerkLockUserTool: ToolConfig<ClerkLockUserParams, ClerkLockUserRes
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/users/${params.userId?.trim()}/lock`,
+    url: (params) =>
+      `https://api.clerk.com/v1/users/${safeUrlPathSegment(params.userId, 'userId')}/lock`,
     method: 'POST',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/path_safety.test.ts b/apps/sim/tools/clerk/path_safety.test.ts
new file mode 100644
index 00000000000..bb499d8a17d
--- /dev/null
+++ b/apps/sim/tools/clerk/path_safety.test.ts
@@ -0,0 +1,229 @@
+/**
+ * @vitest-environment node
+ *
+ * Guards every Clerk tool against path traversal through an LLM-writable ID
+ * that gets interpolated into the request path.
+ *
+ * This is the highest-value surface of the three services hardened together:
+ * the Clerk credential is a backend API key carrying full user-management
+ * authority. The affected IDs — `userId`, `organizationId`, `sessionId`,
+ * `identifierId`, `templateId`, `actorTokenId`, and the OAuth `provider` slug —
+ * are `visibility: 'user-or-llm'`, so prompt injection controls them.
+ * Interpolating one raw let a value like `../../users/user_victim` escape its
+ * API prefix once `fetch` normalized the URL, re-aiming the request — and that
+ * secret key — at an arbitrary Clerk resource, including on the delete, ban,
+ * and lock routes. `assertRequestUrlMatchesTrust` in
+ * `tools/request-transport.ts` only applies its canonicalization guard to
+ * internal `/api/` routes, so nothing downstream catches this.
+ *
+ * Wrapping the ID in `encodeURIComponent` is NOT enough, which is why the
+ * vector list below includes the bare `.` and `..` segments: both are made of
+ * unreserved characters, so they survive encoding untouched and the URL parser
+ * then removes them as dot segments, popping one path segment off a fixed host.
+ * Every assertion here resolves the built URL with `new URL(...)` — the same
+ * normalization `fetch` performs — rather than string-matching the template
+ * output, because string matching is exactly what let this through.
+ *
+ * The suite enumerates the tool barrel and then, per tool, every declared
+ * parameter that reaches a path segment, fuzzing **one parameter at a time**
+ * while the others hold a safe value. A new tool — or a new ID parameter on an
+ * existing tool — is therefore covered without anyone remembering to register
+ * it, and a still-guarded sibling parameter cannot mask an unguarded one by
+ * throwing first.
+ *
+ * Discovery inspects what `request.url` returns. That is total for this
+ * service: no Clerk tool issues a `fetch` of its own from `transformResponse`,
+ * so `request.url` is the only place a URL is built. Jira does build a second
+ * URL there, and its suite carries an extra block for it — if a Clerk tool ever
+ * grows one, this file needs the same.
+ */
+import { describe, expect, it } from 'vitest'
+import * as clerkTools from '@/tools/clerk/index'
+
+/**
+ * The bare `.` and `..` entries are the whole point: their omission is why an
+ * `encodeURIComponent`-only fix looks correct while the hole stays live.
+ */
+const TRAVERSAL_IDS = [
+  '..',
+  '.',
+  '  ..  ',
+  '../../users/user_victim',
+  '..%2f..%2fusers/user_victim',
+  'user_abc/../../../organizations/org_victim',
+  'user_abc?injectedProbe=attacker',
+  'user_abc#fragment',
+  'user_abc/sessions/../../../users',
+  '\\..\\..',
+] as const
+
+/** Values a real user legitimately supplies; none may be rejected or altered. */
+const LEGITIMATE_IDS = [
+  'user_2abcDEF',
+  'user_2NNEqL2nrIRdJ194ndJqAHwEfxC',
+  'org_2abcDEF',
+  'sess_2abcDEF',
+  'alid_2abcDEF',
+  'jtmp_2abcDEF',
+  'google',
+  'v1.2.3',
+  '..foo',
+  'foo..',
+] as const
+
+const SAFE_ID = 'SAFEID'
+
+/** Sentinel for the one parameter under test, so its slots are identifiable. */
+const PROBE_ID = 'PROBEID'
+
+const BASE_ORIGIN = 'https://api.clerk.com'
+
+/** Every Clerk backend route this integration calls lives under this prefix. */
+const BASE_PATH = '/v1/'
+
+/** Supplied by the platform, never by the model. */
+const FIXED_PARAMS: Record<string, unknown> = { secretKey: 'sk_test_token' }
+
+/**
+ * The slice of a tool this suite drives. Narrowing to it — rather than reaching
+ * for `ToolConfig<any, any>` and an `as any` at the call site — keeps the
+ * harness typed end to end while staying agnostic about each tool's own param
+ * and response generics, which differ per tool and are irrelevant here.
+ */
+type ToolParams = Record<string, unknown>
+
+type UrlBuilder = (params: ToolParams) => string
+
+interface ParamDefinition {
+  readonly type?: string
+}
+
+interface PathBuildingTool {
+  readonly id: string
+  readonly params: Readonly<Record<string, ParamDefinition>>
+  readonly buildUrl: UrlBuilder
+}
+
+/**
+ * Narrows a barrel export to a Clerk tool that builds its URL from params.
+ * Anything else — a type-only re-export, a tool with a static URL — yields
+ * `null` and drops out of the suite.
+ */
+function asPathBuildingTool(value: unknown): PathBuildingTool | null {
+  if (typeof value !== 'object' || value === null) return null
+
+  const candidate = value as { id?: unknown; params?: unknown; request?: unknown }
+  if (typeof candidate.id !== 'string' || !candidate.id.startsWith('clerk_')) return null
+
+  const request = candidate.request as { url?: unknown } | undefined
+  if (typeof request?.url !== 'function') return null
+
+  return {
+    id: candidate.id,
+    params: (candidate.params ?? {}) as Record<string, ParamDefinition>,
+    buildUrl: request.url as UrlBuilder,
+  }
+}
+
+/**
+ * Fills every declared parameter with a type-appropriate safe value, then
+ * overrides the single parameter under test.
+ */
+function buildParams(tool: PathBuildingTool, paramName: string, value: string): ToolParams {
+  const params: ToolParams = {}
+  for (const [name, definition] of Object.entries(tool.params)) {
+    if (definition.type === 'json' || definition.type === 'array') {
+      params[name] = []
+    } else if (definition.type === 'number') {
+      params[name] = 1
+    } else if (definition.type === 'boolean') {
+      params[name] = false
+    } else {
+      params[name] = SAFE_ID
+    }
+  }
+  Object.assign(params, FIXED_PARAMS)
+  params[paramName] = value
+  return params
+}
+
+function buildUrl(tool: PathBuildingTool, paramName: string, value: string): URL {
+  return new URL(tool.buildUrl(buildParams(tool, paramName, value)))
+}
+
+function segmentsOf(tool: PathBuildingTool, paramName: string, value: string): string[] {
+  return buildUrl(tool, paramName, value).pathname.split('/')
+}
+
+/** Every (tool, parameter) pair whose value lands in a URL path segment. */
+const PATH_PARAMS = Object.values(clerkTools)
+  .map(asPathBuildingTool)
+  .filter((tool): tool is PathBuildingTool => tool !== null)
+  .flatMap((tool) =>
+    Object.keys(tool.params)
+      .filter((name) => !(name in FIXED_PARAMS))
+      .filter((name) => {
+        try {
+          return buildUrl(tool, name, PROBE_ID).pathname.includes(PROBE_ID)
+        } catch {
+          return false
+        }
+      })
+      .map((name) => ({ label: `${tool.id} :: ${name}`, tool, paramName: name }))
+  )
+
+describe('clerk path-ID traversal safety', () => {
+  it('covers every Clerk parameter that reaches a URL path segment', () => {
+    expect(PATH_PARAMS.length).toBeGreaterThanOrEqual(26)
+  })
+
+  describe.each(PATH_PARAMS)('$label', ({ tool, paramName }) => {
+    const baseline = segmentsOf(tool, paramName, PROBE_ID)
+
+    it('stays under the Clerk backend API prefix', () => {
+      expect(buildUrl(tool, paramName, PROBE_ID).pathname.startsWith(BASE_PATH)).toBe(true)
+    })
+
+    it.each(TRAVERSAL_IDS)('cannot reshape the path with %j', (value) => {
+      let url: URL
+      try {
+        url = buildUrl(tool, paramName, value)
+      } catch {
+        return
+      }
+
+      expect(url.origin).toBe(BASE_ORIGIN)
+      expect(url.pathname.startsWith(BASE_PATH)).toBe(true)
+
+      const actual = url.pathname.split('/')
+      expect(actual).toHaveLength(baseline.length)
+      baseline.forEach((segment, index) => {
+        if (segment.includes(PROBE_ID)) return
+        expect(actual[index]).toBe(segment)
+      })
+    })
+
+    it.each(['..', '.'] as const)('rejects the bare %j segment by name', (value) => {
+      expect(() => buildUrl(tool, paramName, value)).toThrow(new RegExp(paramName))
+    })
+
+    it.each(LEGITIMATE_IDS)('passes %j through unchanged', (value) => {
+      const actual = segmentsOf(tool, paramName, value)
+
+      expect(actual).toHaveLength(baseline.length)
+      baseline.forEach((segment, index) => {
+        expect(actual[index]).toBe(segment.split(PROBE_ID).join(value))
+      })
+    })
+
+    it('trims surrounding whitespace without altering the id', () => {
+      expect(segmentsOf(tool, paramName, `  ${PROBE_ID}  `)).toEqual(baseline)
+    })
+
+    it('does not let the id inject a query parameter', () => {
+      const url = buildUrl(tool, paramName, `${PROBE_ID}?injectedProbe=attacker`)
+
+      expect(url.searchParams.get('injectedProbe')).toBeNull()
+    })
+  })
+})
diff --git a/apps/sim/tools/clerk/remove_organization_member.ts b/apps/sim/tools/clerk/remove_organization_member.ts
index 9b35396661d..4acc3cb0080 100644
--- a/apps/sim/tools/clerk/remove_organization_member.ts
+++ b/apps/sim/tools/clerk/remove_organization_member.ts
@@ -6,6 +6,7 @@ import type {
   ClerkRemoveOrganizationMemberResponse,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkRemoveOrganizationMember')
 
@@ -41,7 +42,7 @@ export const clerkRemoveOrganizationMemberTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}/memberships/${params.userId?.trim()}`,
+      `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}/memberships/${safeUrlPathSegment(params.userId, 'userId')}`,
     method: 'DELETE',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/revoke_actor_token.ts b/apps/sim/tools/clerk/revoke_actor_token.ts
index 2457dbcb330..494e52fca7a 100644
--- a/apps/sim/tools/clerk/revoke_actor_token.ts
+++ b/apps/sim/tools/clerk/revoke_actor_token.ts
@@ -6,6 +6,7 @@ import type {
   ClerkRevokeActorTokenResponse,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkRevokeActorToken')
 
@@ -34,7 +35,8 @@ export const clerkRevokeActorTokenTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/actor_tokens/${params.actorTokenId?.trim()}/revoke`,
+    url: (params) =>
+      `https://api.clerk.com/v1/actor_tokens/${safeUrlPathSegment(params.actorTokenId, 'actorTokenId')}/revoke`,
     method: 'POST',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/revoke_session.ts b/apps/sim/tools/clerk/revoke_session.ts
index 311ead427e8..7c226d85d4a 100644
--- a/apps/sim/tools/clerk/revoke_session.ts
+++ b/apps/sim/tools/clerk/revoke_session.ts
@@ -6,6 +6,7 @@ import type {
   ClerkSession,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkRevokeSession')
 
@@ -34,7 +35,8 @@ export const clerkRevokeSessionTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/sessions/${params.sessionId?.trim()}/revoke`,
+    url: (params) =>
+      `https://api.clerk.com/v1/sessions/${safeUrlPathSegment(params.sessionId, 'sessionId')}/revoke`,
     method: 'POST',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/unban_user.ts b/apps/sim/tools/clerk/unban_user.ts
index f025775e1c6..e3e30919b9f 100644
--- a/apps/sim/tools/clerk/unban_user.ts
+++ b/apps/sim/tools/clerk/unban_user.ts
@@ -6,6 +6,7 @@ import type {
   ClerkUser,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkUnbanUser')
 
@@ -31,7 +32,8 @@ export const clerkUnbanUserTool: ToolConfig<ClerkUnbanUserParams, ClerkUnbanUser
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/users/${params.userId?.trim()}/unban`,
+    url: (params) =>
+      `https://api.clerk.com/v1/users/${safeUrlPathSegment(params.userId, 'userId')}/unban`,
     method: 'POST',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/unlock_user.ts b/apps/sim/tools/clerk/unlock_user.ts
index 9c0ef1b8018..d067cfd44a9 100644
--- a/apps/sim/tools/clerk/unlock_user.ts
+++ b/apps/sim/tools/clerk/unlock_user.ts
@@ -6,6 +6,7 @@ import type {
   ClerkUser,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkUnlockUser')
 
@@ -31,7 +32,8 @@ export const clerkUnlockUserTool: ToolConfig<ClerkUnlockUserParams, ClerkUnlockU
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/users/${params.userId?.trim()}/unlock`,
+    url: (params) =>
+      `https://api.clerk.com/v1/users/${safeUrlPathSegment(params.userId, 'userId')}/unlock`,
     method: 'POST',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/update_organization.ts b/apps/sim/tools/clerk/update_organization.ts
index 201fc650b22..eec4d42eed3 100644
--- a/apps/sim/tools/clerk/update_organization.ts
+++ b/apps/sim/tools/clerk/update_organization.ts
@@ -6,6 +6,7 @@ import type {
   ClerkUpdateOrganizationResponse,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkUpdateOrganization')
 
@@ -58,7 +59,8 @@ export const clerkUpdateOrganizationTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}`,
+    url: (params) =>
+      `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}`,
     method: 'PATCH',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/update_organization_membership.ts b/apps/sim/tools/clerk/update_organization_membership.ts
index d7cb8f8ae21..a2eeccb037c 100644
--- a/apps/sim/tools/clerk/update_organization_membership.ts
+++ b/apps/sim/tools/clerk/update_organization_membership.ts
@@ -6,6 +6,7 @@ import type {
   ClerkUpdateOrganizationMembershipResponse,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkUpdateOrganizationMembership')
 
@@ -47,7 +48,7 @@ export const clerkUpdateOrganizationMembershipTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.clerk.com/v1/organizations/${params.organizationId?.trim()}/memberships/${params.userId?.trim()}`,
+      `https://api.clerk.com/v1/organizations/${safeUrlPathSegment(params.organizationId, 'organizationId')}/memberships/${safeUrlPathSegment(params.userId, 'userId')}`,
     method: 'PATCH',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/clerk/update_user.ts b/apps/sim/tools/clerk/update_user.ts
index 776feef5069..9c75e3c3559 100644
--- a/apps/sim/tools/clerk/update_user.ts
+++ b/apps/sim/tools/clerk/update_user.ts
@@ -8,6 +8,7 @@ import type {
   ClerkUser,
 } from '@/tools/clerk/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('ClerkUpdateUser')
 
@@ -99,7 +100,8 @@ export const clerkUpdateUserTool: ToolConfig<ClerkUpdateUserParams, ClerkUpdateU
   },
 
   request: {
-    url: (params) => `https://api.clerk.com/v1/users/${params.userId?.trim()}`,
+    url: (params) =>
+      `https://api.clerk.com/v1/users/${safeUrlPathSegment(params.userId, 'userId')}`,
     method: 'PATCH',
     headers: (params) => {
       if (!params.secretKey) {
diff --git a/apps/sim/tools/jira/add_comment.ts b/apps/sim/tools/jira/add_comment.ts
index 7d784b39029..4fd71696468 100644
--- a/apps/sim/tools/jira/add_comment.ts
+++ b/apps/sim/tools/jira/add_comment.ts
@@ -2,6 +2,7 @@ import type { JiraAddCommentParams, JiraAddCommentResponse } from '@/tools/jira/
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT, USER_OUTPUT_PROPERTIES } from '@/tools/jira/types'
 import { extractAdfText, getJiraCloudId, toAdf, transformUser } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 /**
  * Transforms an add comment API response into typed output.
@@ -74,7 +75,7 @@ export const jiraAddCommentTool: ToolConfig<JiraAddCommentParams, JiraAddComment
   request: {
     url: (params: JiraAddCommentParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/comment`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/comment`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -99,7 +100,7 @@ export const jiraAddCommentTool: ToolConfig<JiraAddCommentParams, JiraAddComment
     if (params?.visibility) payload.visibility = params.visibility
 
     const makeRequest = async (cloudId: string) => {
-      const commentUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/comment`
+      const commentUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/comment`
       const commentResponse = await fetch(commentUrl, {
         method: 'POST',
         headers: {
diff --git a/apps/sim/tools/jira/add_watcher.ts b/apps/sim/tools/jira/add_watcher.ts
index 65419b59be6..762ad09ef49 100644
--- a/apps/sim/tools/jira/add_watcher.ts
+++ b/apps/sim/tools/jira/add_watcher.ts
@@ -2,6 +2,7 @@ import type { JiraAddWatcherParams, JiraAddWatcherResponse } from '@/tools/jira/
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraAddWatcherTool: ToolConfig<JiraAddWatcherParams, JiraAddWatcherResponse> = {
   id: 'jira_add_watcher',
@@ -51,7 +52,7 @@ export const jiraAddWatcherTool: ToolConfig<JiraAddWatcherParams, JiraAddWatcher
   request: {
     url: (params: JiraAddWatcherParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/watchers`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/watchers`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -78,7 +79,7 @@ export const jiraAddWatcherTool: ToolConfig<JiraAddWatcherParams, JiraAddWatcher
     }
     if (!params?.cloudId) {
       const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
-      const watcherUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/watchers`
+      const watcherUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/watchers`
       const watcherResponse = await fetch(watcherUrl, {
         method: 'POST',
         headers: {
diff --git a/apps/sim/tools/jira/add_worklog.ts b/apps/sim/tools/jira/add_worklog.ts
index 8a92287907b..d89958899d0 100644
--- a/apps/sim/tools/jira/add_worklog.ts
+++ b/apps/sim/tools/jira/add_worklog.ts
@@ -7,6 +7,7 @@ import {
   transformUser,
 } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 /**
  * Builds the worklog request body per Jira API v3.
@@ -109,7 +110,7 @@ export const jiraAddWorklogTool: ToolConfig<JiraAddWorklogParams, JiraAddWorklog
   request: {
     url: (params: JiraAddWorklogParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/worklog`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/worklog`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -134,7 +135,7 @@ export const jiraAddWorklogTool: ToolConfig<JiraAddWorklogParams, JiraAddWorklog
     }
 
     const makeRequest = async (cloudId: string) => {
-      const worklogUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/worklog`
+      const worklogUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/worklog`
       const worklogResponse = await fetch(worklogUrl, {
         method: 'POST',
         headers: {
diff --git a/apps/sim/tools/jira/assign_issue.ts b/apps/sim/tools/jira/assign_issue.ts
index 7312a006883..14bf30ac703 100644
--- a/apps/sim/tools/jira/assign_issue.ts
+++ b/apps/sim/tools/jira/assign_issue.ts
@@ -2,6 +2,7 @@ import type { JiraAssignIssueParams, JiraAssignIssueResponse } from '@/tools/jir
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 /**
  * Maps user-provided accountId to the Jira API value.
@@ -66,7 +67,7 @@ export const jiraAssignIssueTool: ToolConfig<JiraAssignIssueParams, JiraAssignIs
   request: {
     url: (params: JiraAssignIssueParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/assignee`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/assignee`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -87,7 +88,7 @@ export const jiraAssignIssueTool: ToolConfig<JiraAssignIssueParams, JiraAssignIs
   transformResponse: async (response: Response, params?: JiraAssignIssueParams) => {
     if (!params?.cloudId) {
       const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
-      const assignUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/assignee`
+      const assignUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/assignee`
       const assignResponse = await fetch(assignUrl, {
         method: 'PUT',
         headers: {
diff --git a/apps/sim/tools/jira/bulk_read.ts b/apps/sim/tools/jira/bulk_read.ts
index ac6a55add87..36d129efa08 100644
--- a/apps/sim/tools/jira/bulk_read.ts
+++ b/apps/sim/tools/jira/bulk_read.ts
@@ -3,6 +3,7 @@ import type { JiraRetrieveBulkParams, JiraRetrieveResponseBulk } from '@/tools/j
 import { TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { extractAdfText } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraBulkRetrieveTool: ToolConfig<JiraRetrieveBulkParams, JiraRetrieveResponseBulk> = {
   id: 'jira_bulk_read',
@@ -59,7 +60,7 @@ export const jiraBulkRetrieveTool: ToolConfig<JiraRetrieveBulkParams, JiraRetrie
     const resolveProjectKey = async (cloudId: string, accessToken: string, ref: string) => {
       const refTrimmed = (ref || '').trim()
       if (!refTrimmed) return refTrimmed
-      const url = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/project/${encodeURIComponent(refTrimmed)}`
+      const url = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/project/${safeUrlPathSegment(refTrimmed, 'projectId')}`
       const resp = await fetch(url, {
         method: 'GET',
         headers: { Authorization: `Bearer ${accessToken}`, Accept: 'application/json' },
diff --git a/apps/sim/tools/jira/delete_attachment.ts b/apps/sim/tools/jira/delete_attachment.ts
index 62f9b6afbb9..c5bb4fef8ce 100644
--- a/apps/sim/tools/jira/delete_attachment.ts
+++ b/apps/sim/tools/jira/delete_attachment.ts
@@ -2,6 +2,7 @@ import type { JiraDeleteAttachmentParams, JiraDeleteAttachmentResponse } from '@
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraDeleteAttachmentTool: ToolConfig<
   JiraDeleteAttachmentParams,
@@ -48,7 +49,7 @@ export const jiraDeleteAttachmentTool: ToolConfig<
   request: {
     url: (params: JiraDeleteAttachmentParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/attachment/${params.attachmentId?.trim() ?? ''}`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/attachment/${safeUrlPathSegment(params.attachmentId, 'attachmentId')}`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -65,7 +66,7 @@ export const jiraDeleteAttachmentTool: ToolConfig<
     if (!params?.cloudId) {
       const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
       // Make the actual request with the resolved cloudId
-      const attachmentUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/attachment/${params?.attachmentId?.trim() ?? ''}`
+      const attachmentUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/attachment/${safeUrlPathSegment(params!.attachmentId, 'attachmentId')}`
       const attachmentResponse = await fetch(attachmentUrl, {
         method: 'DELETE',
         headers: {
diff --git a/apps/sim/tools/jira/delete_comment.ts b/apps/sim/tools/jira/delete_comment.ts
index 526f38c98ef..2486c8fafb5 100644
--- a/apps/sim/tools/jira/delete_comment.ts
+++ b/apps/sim/tools/jira/delete_comment.ts
@@ -2,6 +2,7 @@ import type { JiraDeleteCommentParams, JiraDeleteCommentResponse } from '@/tools
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraDeleteCommentTool: ToolConfig<JiraDeleteCommentParams, JiraDeleteCommentResponse> =
   {
@@ -52,7 +53,7 @@ export const jiraDeleteCommentTool: ToolConfig<JiraDeleteCommentParams, JiraDele
     request: {
       url: (params: JiraDeleteCommentParams) => {
         if (params.cloudId) {
-          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/comment/${params.commentId?.trim() ?? ''}`
+          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/comment/${safeUrlPathSegment(params.commentId, 'commentId')}`
         }
         return 'https://api.atlassian.com/oauth/token/accessible-resources'
       },
@@ -69,7 +70,7 @@ export const jiraDeleteCommentTool: ToolConfig<JiraDeleteCommentParams, JiraDele
       if (!params?.cloudId) {
         const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
         // Make the actual request with the resolved cloudId
-        const commentUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params?.issueKey?.trim() ?? ''}/comment/${params?.commentId?.trim() ?? ''}`
+        const commentUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/comment/${safeUrlPathSegment(params!.commentId, 'commentId')}`
         const commentResponse = await fetch(commentUrl, {
           method: 'DELETE',
           headers: {
diff --git a/apps/sim/tools/jira/delete_issue.ts b/apps/sim/tools/jira/delete_issue.ts
index 19a0f61d0ae..3228eccc468 100644
--- a/apps/sim/tools/jira/delete_issue.ts
+++ b/apps/sim/tools/jira/delete_issue.ts
@@ -2,6 +2,7 @@ import type { JiraDeleteIssueParams, JiraDeleteIssueResponse } from '@/tools/jir
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraDeleteIssueTool: ToolConfig<JiraDeleteIssueParams, JiraDeleteIssueResponse> = {
   id: 'jira_delete_issue',
@@ -53,7 +54,7 @@ export const jiraDeleteIssueTool: ToolConfig<JiraDeleteIssueParams, JiraDeleteIs
     url: (params: JiraDeleteIssueParams) => {
       if (params.cloudId) {
         const deleteSubtasksParam = params.deleteSubtasks ? '?deleteSubtasks=true' : ''
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}${deleteSubtasksParam}`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}${deleteSubtasksParam}`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -70,7 +71,7 @@ export const jiraDeleteIssueTool: ToolConfig<JiraDeleteIssueParams, JiraDeleteIs
     if (!params?.cloudId) {
       const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
       const deleteSubtasksParam = params!.deleteSubtasks ? '?deleteSubtasks=true' : ''
-      const deleteUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}${deleteSubtasksParam}`
+      const deleteUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}${deleteSubtasksParam}`
       const deleteResponse = await fetch(deleteUrl, {
         method: 'DELETE',
         headers: {
diff --git a/apps/sim/tools/jira/delete_issue_link.ts b/apps/sim/tools/jira/delete_issue_link.ts
index bc42e97f50b..0dd7d224ee8 100644
--- a/apps/sim/tools/jira/delete_issue_link.ts
+++ b/apps/sim/tools/jira/delete_issue_link.ts
@@ -2,6 +2,7 @@ import type { JiraDeleteIssueLinkParams, JiraDeleteIssueLinkResponse } from '@/t
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraDeleteIssueLinkTool: ToolConfig<
   JiraDeleteIssueLinkParams,
@@ -48,7 +49,7 @@ export const jiraDeleteIssueLinkTool: ToolConfig<
   request: {
     url: (params: JiraDeleteIssueLinkParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issueLink/${params.linkId?.trim() ?? ''}`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issueLink/${safeUrlPathSegment(params.linkId, 'linkId')}`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -64,7 +65,7 @@ export const jiraDeleteIssueLinkTool: ToolConfig<
   transformResponse: async (response: Response, params?: JiraDeleteIssueLinkParams) => {
     if (!params?.cloudId) {
       const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
-      const issueLinkUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issueLink/${params!.linkId?.trim() ?? ''}`
+      const issueLinkUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issueLink/${safeUrlPathSegment(params!.linkId, 'linkId')}`
       const issueLinkResponse = await fetch(issueLinkUrl, {
         method: 'DELETE',
         headers: {
diff --git a/apps/sim/tools/jira/delete_worklog.ts b/apps/sim/tools/jira/delete_worklog.ts
index b43faecb00a..0a6a674137e 100644
--- a/apps/sim/tools/jira/delete_worklog.ts
+++ b/apps/sim/tools/jira/delete_worklog.ts
@@ -2,6 +2,7 @@ import type { JiraDeleteWorklogParams, JiraDeleteWorklogResponse } from '@/tools
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraDeleteWorklogTool: ToolConfig<JiraDeleteWorklogParams, JiraDeleteWorklogResponse> =
   {
@@ -52,7 +53,7 @@ export const jiraDeleteWorklogTool: ToolConfig<JiraDeleteWorklogParams, JiraDele
     request: {
       url: (params: JiraDeleteWorklogParams) => {
         if (params.cloudId) {
-          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/worklog/${params.worklogId?.trim() ?? ''}`
+          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/worklog/${safeUrlPathSegment(params.worklogId, 'worklogId')}`
         }
         return 'https://api.atlassian.com/oauth/token/accessible-resources'
       },
@@ -68,7 +69,7 @@ export const jiraDeleteWorklogTool: ToolConfig<JiraDeleteWorklogParams, JiraDele
     transformResponse: async (response: Response, params?: JiraDeleteWorklogParams) => {
       if (!params?.cloudId) {
         const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
-        const worklogUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/worklog/${params!.worklogId?.trim() ?? ''}`
+        const worklogUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/worklog/${safeUrlPathSegment(params!.worklogId, 'worklogId')}`
         const worklogResponse = await fetch(worklogUrl, {
           method: 'DELETE',
           headers: {
diff --git a/apps/sim/tools/jira/get_attachments.ts b/apps/sim/tools/jira/get_attachments.ts
index 2bcc027d18d..57d21d2d753 100644
--- a/apps/sim/tools/jira/get_attachments.ts
+++ b/apps/sim/tools/jira/get_attachments.ts
@@ -2,6 +2,7 @@ import type { JiraGetAttachmentsParams, JiraGetAttachmentsResponse } from '@/too
 import { ATTACHMENT_ITEM_PROPERTIES, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { downloadJiraAttachments, getJiraCloudId, transformUser } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 /**
  * Transforms a raw Jira attachment object into typed output.
@@ -72,7 +73,7 @@ export const jiraGetAttachmentsTool: ToolConfig<
   request: {
     url: (params: JiraGetAttachmentsParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}?fields=attachment`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}?fields=attachment`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -87,7 +88,7 @@ export const jiraGetAttachmentsTool: ToolConfig<
 
   transformResponse: async (response: Response, params?: JiraGetAttachmentsParams) => {
     const fetchAttachments = async (cloudId: string) => {
-      const attachmentsUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}?fields=attachment`
+      const attachmentsUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}?fields=attachment`
       const attachmentsResponse = await fetch(attachmentsUrl, {
         method: 'GET',
         headers: {
diff --git a/apps/sim/tools/jira/get_comments.ts b/apps/sim/tools/jira/get_comments.ts
index 6e2876f5768..72ff594c31e 100644
--- a/apps/sim/tools/jira/get_comments.ts
+++ b/apps/sim/tools/jira/get_comments.ts
@@ -2,6 +2,7 @@ import type { JiraGetCommentsParams, JiraGetCommentsResponse } from '@/tools/jir
 import { COMMENT_ITEM_PROPERTIES, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { extractAdfText, getJiraCloudId, transformUser } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 /**
  * Transforms a raw Jira comment object into typed output.
@@ -85,7 +86,7 @@ export const jiraGetCommentsTool: ToolConfig<JiraGetCommentsParams, JiraGetComme
         const startAt = params.startAt ?? 0
         const maxResults = params.maxResults ?? 50
         const orderBy = params.orderBy ?? '-created'
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/comment?startAt=${startAt}&maxResults=${maxResults}&orderBy=${orderBy}`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/comment?startAt=${startAt}&maxResults=${maxResults}&orderBy=${orderBy}`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -103,7 +104,7 @@ export const jiraGetCommentsTool: ToolConfig<JiraGetCommentsParams, JiraGetComme
       const startAt = params?.startAt ?? 0
       const maxResults = params?.maxResults ?? 50
       const orderBy = params?.orderBy ?? '-created'
-      const commentsUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/comment?startAt=${startAt}&maxResults=${maxResults}&orderBy=${orderBy}`
+      const commentsUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/comment?startAt=${startAt}&maxResults=${maxResults}&orderBy=${orderBy}`
       const commentsResponse = await fetch(commentsUrl, {
         method: 'GET',
         headers: {
diff --git a/apps/sim/tools/jira/get_project.ts b/apps/sim/tools/jira/get_project.ts
index 6e4db960d15..2876ddf6dd3 100644
--- a/apps/sim/tools/jira/get_project.ts
+++ b/apps/sim/tools/jira/get_project.ts
@@ -2,9 +2,10 @@ import type { JiraGetProjectParams, JiraGetProjectResponse } from '@/tools/jira/
 import { TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId, parseAtlassianErrorMessage } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 function buildProjectUrl(cloudId: string, projectIdOrKey: string): string {
-  return `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/project/${encodeURIComponent(projectIdOrKey)}`
+  return `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/project/${safeUrlPathSegment(projectIdOrKey, 'projectId')}`
 }
 
 export const jiraGetProjectTool: ToolConfig<JiraGetProjectParams, JiraGetProjectResponse> = {
diff --git a/apps/sim/tools/jira/get_transitions.ts b/apps/sim/tools/jira/get_transitions.ts
index 94f92df44dc..ffa1803e405 100644
--- a/apps/sim/tools/jira/get_transitions.ts
+++ b/apps/sim/tools/jira/get_transitions.ts
@@ -2,9 +2,10 @@ import type { JiraGetTransitionsParams, JiraGetTransitionsResponse } from '@/too
 import { TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId, parseAtlassianErrorMessage } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 function buildTransitionsUrl(cloudId: string, issueKey: string): string {
-  return `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${encodeURIComponent(issueKey)}/transitions`
+  return `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(issueKey, 'issueKey')}/transitions`
 }
 
 export const jiraGetTransitionsTool: ToolConfig<
diff --git a/apps/sim/tools/jira/get_worklogs.ts b/apps/sim/tools/jira/get_worklogs.ts
index c788fe2af2a..c49fb27d3b0 100644
--- a/apps/sim/tools/jira/get_worklogs.ts
+++ b/apps/sim/tools/jira/get_worklogs.ts
@@ -2,6 +2,7 @@ import type { JiraGetWorklogsParams, JiraGetWorklogsResponse } from '@/tools/jir
 import { TIMESTAMP_OUTPUT, WORKLOG_ITEM_PROPERTIES } from '@/tools/jira/types'
 import { extractAdfText, getJiraCloudId, transformUser } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 /**
  * Transforms a raw Jira worklog object into typed output.
@@ -77,7 +78,7 @@ export const jiraGetWorklogsTool: ToolConfig<JiraGetWorklogsParams, JiraGetWorkl
       if (params.cloudId) {
         const startAt = params.startAt ?? 0
         const maxResults = params.maxResults ?? 50
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/worklog?startAt=${startAt}&maxResults=${maxResults}`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/worklog?startAt=${startAt}&maxResults=${maxResults}`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -94,7 +95,7 @@ export const jiraGetWorklogsTool: ToolConfig<JiraGetWorklogsParams, JiraGetWorkl
     const fetchWorklogs = async (cloudId: string) => {
       const startAt = params?.startAt ?? 0
       const maxResults = params?.maxResults ?? 50
-      const worklogsUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/worklog?startAt=${startAt}&maxResults=${maxResults}`
+      const worklogsUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/worklog?startAt=${startAt}&maxResults=${maxResults}`
       const worklogsResponse = await fetch(worklogsUrl, {
         method: 'GET',
         headers: {
diff --git a/apps/sim/tools/jira/path_safety.test.ts b/apps/sim/tools/jira/path_safety.test.ts
new file mode 100644
index 00000000000..cae1db216d6
--- /dev/null
+++ b/apps/sim/tools/jira/path_safety.test.ts
@@ -0,0 +1,389 @@
+/**
+ * @vitest-environment node
+ *
+ * Guards every Jira tool against path traversal through an LLM-writable ID
+ * that gets interpolated into the request path.
+ *
+ * `issueKey`, `commentId`, `worklogId`, `attachmentId`, `linkId`, and
+ * `projectId` are `visibility: 'user-or-llm'`, so prompt injection controls
+ * them. Interpolating one raw let a value like `../../../project/OTHER` escape
+ * its `/rest/api/3/issue/` prefix once `fetch` normalized the URL, re-aiming
+ * the request — and the user's Atlassian OAuth token — at a different resource
+ * on the same site, including on DELETE. `assertRequestUrlMatchesTrust` in
+ * `tools/request-transport.ts` only applies its canonicalization guard to
+ * internal `/api/` routes, so nothing downstream catches this.
+ *
+ * `cloudId` is deliberately pinned here rather than fuzzed. It is
+ * `visibility: 'hidden'`, no Jira block subBlock ever writes it, and its only
+ * real source is `getJiraCloudId` -> `resolveAtlassianCloudId`, which returns a
+ * UUID from Atlassian's own accessible-resources endpoint. Fuzzing it would
+ * assert a threat model that does not exist while masking the parameters that
+ * do carry one. Pinning it also selects the direct-request branch: without a
+ * `cloudId` every tool returns the discovery URL instead.
+ *
+ * Wrapping the ID in `encodeURIComponent` is NOT enough, which is why the
+ * vector list below includes the bare `.` and `..` segments: both are made of
+ * unreserved characters, so they survive encoding untouched and the URL parser
+ * then removes them as dot segments, popping one path segment off a fixed host.
+ * Every assertion here resolves the built URL with `new URL(...)` — the same
+ * normalization `fetch` performs — rather than string-matching the template
+ * output, because string matching is exactly what let this through.
+ *
+ * The suite enumerates the tool barrel and then, per tool, every declared
+ * parameter that reaches a path segment, fuzzing **one parameter at a time**
+ * while the others hold a safe value. A new tool — or a new ID parameter on an
+ * existing tool — is therefore covered without anyone remembering to register
+ * it, and a still-guarded sibling parameter cannot mask an unguarded one by
+ * throwing first.
+ *
+ * Jira builds its URLs in **two** places, and this file has a suite for each.
+ * `request.url` covers the call made when a `cloudId` is already present; the
+ * second block at the bottom covers the URL a tool constructs inside
+ * `transformResponse` after resolving one, which `request.url` cannot expose
+ * (`jira_bulk_read.projectId` reaches a path segment only that way). The
+ * fallback block discovers its parameters by running `transformResponse`
+ * against a stubbed `fetch` and reading back what was requested, so the
+ * enumeration is total for URLs a tool actually sends — a URL a tool built but
+ * never fetched would still be invisible to both.
+ */
+import { describe, expect, it } from 'vitest'
+import * as jiraTools from '@/tools/jira/index'
+
+/**
+ * The bare `.` and `..` entries are the whole point: their omission is why an
+ * `encodeURIComponent`-only fix looks correct while the hole stays live.
+ */
+const TRAVERSAL_IDS = [
+  '..',
+  '.',
+  '  ..  ',
+  '../../../project/OTHER',
+  '..%2f..%2f..%2fproject/OTHER',
+  'PROJ-123/../../../project/OTHER',
+  'PROJ-123?injectedProbe=attacker',
+  'PROJ-123#fragment',
+  'PROJ-123/comment/../../../myself',
+  '\\..\\..',
+] as const
+
+/** Values a real user legitimately supplies; none may be rejected or altered. */
+const LEGITIMATE_IDS = [
+  'PROJ-123',
+  'ABC-1',
+  'MY_PROJECT-4567',
+  '10001',
+  'PROJ',
+  '..foo',
+  'foo..',
+] as const
+
+const SAFE_ID = 'SAFEID'
+
+/** Sentinel for the one parameter under test, so its slots are identifiable. */
+const PROBE_ID = 'PROBEID'
+
+const BASE_ORIGIN = 'https://api.atlassian.com'
+
+const CLOUD_ID = '11111111-2222-4333-8444-555555555555'
+
+/** Every per-site Jira REST call this integration makes lives under this prefix. */
+const BASE_PATH = `/ex/jira/${CLOUD_ID}/rest/api/3/`
+
+/** Supplied by the platform, never by the model. */
+const FIXED_PARAMS: Record<string, unknown> = {
+  accessToken: 'token',
+  domain: 'example.atlassian.net',
+  cloudId: CLOUD_ID,
+}
+
+/**
+ * The slice of a tool this suite drives. Narrowing to it — rather than reaching
+ * for `ToolConfig<any, any>` and an `as any` at the call site — keeps the
+ * harness typed end to end while staying agnostic about each tool's own param
+ * and response generics, which differ per tool and are irrelevant here.
+ */
+type ToolParams = Record<string, unknown>
+
+type UrlBuilder = (params: ToolParams) => string
+
+interface ParamDefinition {
+  readonly type?: string
+}
+
+type TransformResponse = (response: Response, params: ToolParams) => Promise<unknown>
+
+interface PathBuildingTool {
+  readonly id: string
+  readonly params: Readonly<Record<string, ParamDefinition>>
+  readonly buildUrl: UrlBuilder
+  /** Present on the Jira tools that re-issue the call after resolving a cloudId. */
+  readonly transformResponse: TransformResponse | null
+}
+
+/**
+ * Narrows a barrel export to a Jira tool that builds its URL from params.
+ * Anything else — a type-only re-export, a tool with a static URL — yields
+ * `null` and drops out of the suite.
+ */
+function asPathBuildingTool(value: unknown): PathBuildingTool | null {
+  if (typeof value !== 'object' || value === null) return null
+
+  const candidate = value as { id?: unknown; params?: unknown; request?: unknown }
+  if (typeof candidate.id !== 'string' || !candidate.id.startsWith('jira_')) return null
+
+  const request = candidate.request as { url?: unknown } | undefined
+  if (typeof request?.url !== 'function') return null
+
+  return {
+    id: candidate.id,
+    params: (candidate.params ?? {}) as Record<string, ParamDefinition>,
+    buildUrl: request.url as UrlBuilder,
+    transformResponse:
+      typeof candidate.transformResponse === 'function'
+        ? (candidate.transformResponse as TransformResponse)
+        : null,
+  }
+}
+
+/**
+ * Fills every declared parameter with a type-appropriate safe value, then
+ * overrides the single parameter under test.
+ */
+function buildParams(tool: PathBuildingTool, paramName: string, value: string): ToolParams {
+  const params: ToolParams = {}
+  for (const [name, definition] of Object.entries(tool.params)) {
+    if (definition.type === 'json' || definition.type === 'array') {
+      params[name] = []
+    } else if (definition.type === 'number') {
+      params[name] = 1
+    } else if (definition.type === 'boolean') {
+      params[name] = false
+    } else {
+      params[name] = SAFE_ID
+    }
+  }
+  Object.assign(params, FIXED_PARAMS)
+  params[paramName] = value
+  return params
+}
+
+function buildUrl(tool: PathBuildingTool, paramName: string, value: string): URL {
+  return new URL(tool.buildUrl(buildParams(tool, paramName, value)))
+}
+
+function segmentsOf(tool: PathBuildingTool, paramName: string, value: string): string[] {
+  return buildUrl(tool, paramName, value).pathname.split('/')
+}
+
+/** Every (tool, parameter) pair whose value lands in a URL path segment. */
+const PATH_PARAMS = Object.values(jiraTools)
+  .map(asPathBuildingTool)
+  .filter((tool): tool is PathBuildingTool => tool !== null)
+  .flatMap((tool) =>
+    Object.keys(tool.params)
+      .filter((name) => !(name in FIXED_PARAMS))
+      .filter((name) => {
+        try {
+          return buildUrl(tool, name, PROBE_ID).pathname.includes(PROBE_ID)
+        } catch {
+          return false
+        }
+      })
+      .map((name) => ({ label: `${tool.id} :: ${name}`, tool, paramName: name }))
+  )
+
+describe('jira path-ID traversal safety', () => {
+  it('covers every Jira parameter that reaches a URL path segment', () => {
+    expect(PATH_PARAMS.length).toBeGreaterThanOrEqual(23)
+  })
+
+  describe.each(PATH_PARAMS)('$label', ({ tool, paramName }) => {
+    const baseline = segmentsOf(tool, paramName, PROBE_ID)
+
+    it('stays under the resolved cloud instance prefix', () => {
+      expect(buildUrl(tool, paramName, PROBE_ID).pathname.startsWith(BASE_PATH)).toBe(true)
+    })
+
+    it.each(TRAVERSAL_IDS)('cannot reshape the path with %j', (value) => {
+      let url: URL
+      try {
+        url = buildUrl(tool, paramName, value)
+      } catch {
+        return
+      }
+
+      expect(url.origin).toBe(BASE_ORIGIN)
+      expect(url.pathname.startsWith(BASE_PATH)).toBe(true)
+
+      const actual = url.pathname.split('/')
+      expect(actual).toHaveLength(baseline.length)
+      baseline.forEach((segment, index) => {
+        if (segment.includes(PROBE_ID)) return
+        expect(actual[index]).toBe(segment)
+      })
+    })
+
+    it.each(['..', '.'] as const)('rejects the bare %j segment by name', (value) => {
+      expect(() => buildUrl(tool, paramName, value)).toThrow(new RegExp(paramName))
+    })
+
+    it.each(LEGITIMATE_IDS)('passes %j through unchanged', (value) => {
+      const actual = segmentsOf(tool, paramName, value)
+
+      expect(actual).toHaveLength(baseline.length)
+      baseline.forEach((segment, index) => {
+        expect(actual[index]).toBe(segment.split(PROBE_ID).join(value))
+      })
+    })
+
+    it('trims surrounding whitespace without altering the id', () => {
+      expect(segmentsOf(tool, paramName, `  ${PROBE_ID}  `)).toEqual(baseline)
+    })
+
+    it('does not let the id inject a query parameter', () => {
+      const url = buildUrl(tool, paramName, `${PROBE_ID}?injectedProbe=attacker`)
+
+      expect(url.searchParams.get('injectedProbe')).toBeNull()
+    })
+  })
+})
+
+/**
+ * The second URL construction.
+ *
+ * A Jira tool that is invoked without a `cloudId` sends its configured request
+ * to the fixed `accessible-resources` discovery endpoint, then builds the real
+ * per-site URL inside `transformResponse` and issues it with a bare `fetch`.
+ * `PATH_PARAMS` above cannot see that URL — it only inspects what
+ * `request.url` returns — and `jira_bulk_read.projectId` reaches a path segment
+ * *only* through this second construction, so it would otherwise never be
+ * fuzzed at all.
+ *
+ * This block closes that gap by actually running `transformResponse` with the
+ * `cloudId` withheld, against a stubbed `fetch` that records the URLs the tool
+ * asks for. Discovery is driven the same way `PATH_PARAMS` is — probe every
+ * declared parameter, keep the ones that land in a path segment — so a new tool
+ * or a new ID parameter is covered here too, without registration.
+ */
+const DISCOVERY_PAYLOAD = [{ id: CLOUD_ID, url: `https://${FIXED_PARAMS.domain}`, name: 'example' }]
+
+function stubResponse(): Response {
+  return new Response(JSON.stringify(DISCOVERY_PAYLOAD), {
+    status: 200,
+    headers: { 'content-type': 'application/json' },
+  })
+}
+
+function requestedUrl(input: RequestInfo | URL): string {
+  if (typeof input === 'string') return input
+  if (input instanceof URL) return input.href
+  return input.url
+}
+
+/**
+ * Runs a tool's `transformResponse` with `cloudId` withheld and returns the
+ * per-site URLs it tried to fetch. The discovery hop itself is filtered out, and
+ * a throw is swallowed: a guard rejecting the value is a pass, and the only
+ * thing this function reports is what reached the network.
+ */
+async function fallbackUrls(
+  tool: PathBuildingTool,
+  paramName: string,
+  value: string
+): Promise<string[]> {
+  if (!tool.transformResponse) return []
+
+  const requested: string[] = []
+  const originalFetch = globalThis.fetch
+  globalThis.fetch = ((input: RequestInfo | URL) => {
+    requested.push(requestedUrl(input))
+    return Promise.resolve(stubResponse())
+  }) as typeof globalThis.fetch
+
+  const params = buildParams(tool, paramName, value)
+  params.cloudId = undefined
+
+  try {
+    await tool.transformResponse(stubResponse(), params)
+  } catch {
+    /* Only the URLs the tool asked for matter here. */
+  } finally {
+    globalThis.fetch = originalFetch
+  }
+
+  return requested.filter((url) => new URL(url).pathname.startsWith('/ex/jira/'))
+}
+
+async function fallbackPaths(
+  tool: PathBuildingTool,
+  paramName: string,
+  value: string
+): Promise<string[]> {
+  const urls = await fallbackUrls(tool, paramName, value)
+  return urls.map((url) => new URL(url).pathname)
+}
+
+/**
+ * Whether two resolved pathnames differ only where the probe sentinel sat.
+ * Segment *count* is part of the shape, which is what catches a popped prefix:
+ * a removed dot segment always shortens the path by one.
+ */
+function hasSameShape(baseline: string, actual: string): boolean {
+  const baselineSegments = baseline.split('/')
+  const actualSegments = actual.split('/')
+  if (baselineSegments.length !== actualSegments.length) return false
+  return baselineSegments.every(
+    (segment, index) => segment.includes(PROBE_ID) || segment === actualSegments[index]
+  )
+}
+
+const FALLBACK_CANDIDATES = Object.values(jiraTools)
+  .map(asPathBuildingTool)
+  .filter((tool): tool is PathBuildingTool => tool !== null)
+  .filter((tool) => tool.transformResponse !== null)
+  .flatMap((tool) =>
+    Object.keys(tool.params)
+      .filter((name) => !(name in FIXED_PARAMS))
+      .map((name) => ({ label: `${tool.id} :: ${name}`, tool, paramName: name }))
+  )
+
+const FALLBACK_PATH_PARAMS: typeof FALLBACK_CANDIDATES = []
+for (const candidate of FALLBACK_CANDIDATES) {
+  const urls = await fallbackUrls(candidate.tool, candidate.paramName, PROBE_ID)
+  if (urls.some((url) => new URL(url).pathname.includes(PROBE_ID))) {
+    FALLBACK_PATH_PARAMS.push(candidate)
+  }
+}
+
+describe('jira path-ID traversal safety in transformResponse-built URLs', () => {
+  it('covers every parameter that reaches a path segment of the second URL', () => {
+    expect(FALLBACK_PATH_PARAMS.length).toBeGreaterThanOrEqual(24)
+  })
+
+  it('reaches jira_bulk_read.projectId, which request.url cannot expose', () => {
+    expect(FALLBACK_PATH_PARAMS.map((entry) => entry.label)).toContain(
+      'jira_bulk_read :: projectId'
+    )
+  })
+
+  describe.each(FALLBACK_PATH_PARAMS)('$label', ({ tool, paramName }) => {
+    it.each(TRAVERSAL_IDS)('cannot reshape the second URL with %j', async (value) => {
+      const baseline = await fallbackPaths(tool, paramName, PROBE_ID)
+      const actual = await fallbackPaths(tool, paramName, value)
+
+      for (const pathname of actual) {
+        expect(pathname.startsWith(BASE_PATH)).toBe(true)
+        expect(baseline.some((shape) => hasSameShape(shape, pathname))).toBe(true)
+      }
+    })
+
+    it.each(LEGITIMATE_IDS)('passes %j into the second URL unchanged', async (value) => {
+      const baseline = await fallbackPaths(tool, paramName, PROBE_ID)
+      const actual = await fallbackPaths(tool, paramName, value)
+
+      for (const pathname of baseline.filter((entry) => entry.includes(PROBE_ID))) {
+        expect(actual).toContain(pathname.split(PROBE_ID).join(value))
+      }
+    })
+  })
+})
diff --git a/apps/sim/tools/jira/remove_watcher.ts b/apps/sim/tools/jira/remove_watcher.ts
index 03088fef2f1..29bf3cd5d36 100644
--- a/apps/sim/tools/jira/remove_watcher.ts
+++ b/apps/sim/tools/jira/remove_watcher.ts
@@ -2,6 +2,7 @@ import type { JiraRemoveWatcherParams, JiraRemoveWatcherResponse } from '@/tools
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraRemoveWatcherTool: ToolConfig<JiraRemoveWatcherParams, JiraRemoveWatcherResponse> =
   {
@@ -52,7 +53,7 @@ export const jiraRemoveWatcherTool: ToolConfig<JiraRemoveWatcherParams, JiraRemo
     request: {
       url: (params: JiraRemoveWatcherParams) => {
         if (params.cloudId) {
-          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/watchers?accountId=${encodeURIComponent(params.accountId?.trim() ?? '')}`
+          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/watchers?accountId=${encodeURIComponent(params.accountId?.trim() ?? '')}`
         }
         return 'https://api.atlassian.com/oauth/token/accessible-resources'
       },
@@ -68,7 +69,7 @@ export const jiraRemoveWatcherTool: ToolConfig<JiraRemoveWatcherParams, JiraRemo
     transformResponse: async (response: Response, params?: JiraRemoveWatcherParams) => {
       if (!params?.cloudId) {
         const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
-        const watcherUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/watchers?accountId=${encodeURIComponent(params!.accountId?.trim() ?? '')}`
+        const watcherUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/watchers?accountId=${encodeURIComponent(params!.accountId?.trim() ?? '')}`
         const watcherResponse = await fetch(watcherUrl, {
           method: 'DELETE',
           headers: {
diff --git a/apps/sim/tools/jira/retrieve.ts b/apps/sim/tools/jira/retrieve.ts
index a1ad0c30c55..d909e7a0845 100644
--- a/apps/sim/tools/jira/retrieve.ts
+++ b/apps/sim/tools/jira/retrieve.ts
@@ -8,6 +8,7 @@ import {
   transformUser,
 } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 const logger = createLogger('JiraRetrieveTool')
 
@@ -232,7 +233,7 @@ export const jiraRetrieveTool: ToolConfig<JiraRetrieveParams, JiraRetrieveRespon
   request: {
     url: (params: JiraRetrieveParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}?expand=renderedFields,names,schema,transitions,operations,editmeta,changelog,versionedRepresentations`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}?expand=renderedFields,names,schema,transitions,operations,editmeta,changelog,versionedRepresentations`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -251,7 +252,7 @@ export const jiraRetrieveTool: ToolConfig<JiraRetrieveParams, JiraRetrieveRespon
     }
 
     const fetchIssue = async (cloudId: string) => {
-      const issueUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}?expand=renderedFields,names,schema,transitions,operations,editmeta,changelog,versionedRepresentations`
+      const issueUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}?expand=renderedFields,names,schema,transitions,operations,editmeta,changelog,versionedRepresentations`
       const issueResponse = await fetch(issueUrl, {
         method: 'GET',
         headers: {
@@ -273,7 +274,7 @@ export const jiraRetrieveTool: ToolConfig<JiraRetrieveParams, JiraRetrieveRespon
     }
 
     const fetchSupplementary = async (cloudId: string, data: any) => {
-      const base = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}`
+      const base = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}`
       const [commentsResp, worklogResp, watchersResp] = await Promise.all([
         fetch(`${base}/comment?maxResults=100&orderBy=-created`, {
           headers: { Accept: 'application/json', Authorization: `Bearer ${params.accessToken}` },
diff --git a/apps/sim/tools/jira/transition_issue.ts b/apps/sim/tools/jira/transition_issue.ts
index 4ddd33e32ab..398ed4a15c9 100644
--- a/apps/sim/tools/jira/transition_issue.ts
+++ b/apps/sim/tools/jira/transition_issue.ts
@@ -2,6 +2,7 @@ import type { JiraTransitionIssueParams, JiraTransitionIssueResponse } from '@/t
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT } from '@/tools/jira/types'
 import { getJiraCloudId, toAdf } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const jiraTransitionIssueTool: ToolConfig<
   JiraTransitionIssueParams,
@@ -67,7 +68,7 @@ export const jiraTransitionIssueTool: ToolConfig<
   request: {
     url: (params: JiraTransitionIssueParams) => {
       if (params.cloudId) {
-        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/transitions`
+        return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/transitions`
       }
       return 'https://api.atlassian.com/oauth/token/accessible-resources'
     },
@@ -88,7 +89,7 @@ export const jiraTransitionIssueTool: ToolConfig<
   transformResponse: async (response: Response, params?: JiraTransitionIssueParams) => {
     const performTransition = async (cloudId: string) => {
       // First, fetch available transitions to get the name and target status
-      const transitionsUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/transitions`
+      const transitionsUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/transitions`
       const transitionsResp = await fetch(transitionsUrl, {
         method: 'GET',
         headers: {
@@ -158,7 +159,7 @@ export const jiraTransitionIssueTool: ToolConfig<
 
       // Fetch transition metadata for the response
       try {
-        const transitionsUrl = `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/transitions`
+        const transitionsUrl = `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/transitions`
         const transitionsResp = await fetch(transitionsUrl, {
           method: 'GET',
           headers: {
diff --git a/apps/sim/tools/jira/update_comment.ts b/apps/sim/tools/jira/update_comment.ts
index 8e867a1999e..1cb43870fc2 100644
--- a/apps/sim/tools/jira/update_comment.ts
+++ b/apps/sim/tools/jira/update_comment.ts
@@ -2,6 +2,7 @@ import type { JiraUpdateCommentParams, JiraUpdateCommentResponse } from '@/tools
 import { SUCCESS_OUTPUT, TIMESTAMP_OUTPUT, USER_OUTPUT_PROPERTIES } from '@/tools/jira/types'
 import { extractAdfText, getJiraCloudId, toAdf, transformUser } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 /**
  * Transforms an update comment API response into typed output.
@@ -81,7 +82,7 @@ export const jiraUpdateCommentTool: ToolConfig<JiraUpdateCommentParams, JiraUpda
     request: {
       url: (params: JiraUpdateCommentParams) => {
         if (params.cloudId) {
-          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/comment/${params.commentId?.trim() ?? ''}`
+          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/comment/${safeUrlPathSegment(params.commentId, 'commentId')}`
         }
         return 'https://api.atlassian.com/oauth/token/accessible-resources'
       },
@@ -106,7 +107,7 @@ export const jiraUpdateCommentTool: ToolConfig<JiraUpdateCommentParams, JiraUpda
       if (params?.visibility) payload.visibility = params.visibility
 
       const makeRequest = async (cloudId: string) => {
-        const commentUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/comment/${params!.commentId?.trim() ?? ''}`
+        const commentUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/comment/${safeUrlPathSegment(params!.commentId, 'commentId')}`
         const commentResponse = await fetch(commentUrl, {
           method: 'PUT',
           headers: {
diff --git a/apps/sim/tools/jira/update_worklog.ts b/apps/sim/tools/jira/update_worklog.ts
index 86a2c36630f..86f5d521951 100644
--- a/apps/sim/tools/jira/update_worklog.ts
+++ b/apps/sim/tools/jira/update_worklog.ts
@@ -8,6 +8,7 @@ import {
   transformUser,
 } from '@/tools/jira/utils'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 function buildWorklogBody(params: JiraUpdateWorklogParams) {
   let timeSpentSeconds: number | undefined
@@ -122,7 +123,7 @@ export const jiraUpdateWorklogTool: ToolConfig<JiraUpdateWorklogParams, JiraUpda
     request: {
       url: (params: JiraUpdateWorklogParams) => {
         if (params.cloudId) {
-          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${params.issueKey?.trim() ?? ''}/worklog/${params.worklogId?.trim() ?? ''}`
+          return `https://api.atlassian.com/ex/jira/${params.cloudId}/rest/api/3/issue/${safeUrlPathSegment(params.issueKey, 'issueKey')}/worklog/${safeUrlPathSegment(params.worklogId, 'worklogId')}`
         }
         return 'https://api.atlassian.com/oauth/token/accessible-resources'
       },
@@ -143,7 +144,7 @@ export const jiraUpdateWorklogTool: ToolConfig<JiraUpdateWorklogParams, JiraUpda
     transformResponse: async (response: Response, params?: JiraUpdateWorklogParams) => {
       if (!params?.cloudId) {
         const cloudId = await getJiraCloudId(params!.domain, params!.accessToken)
-        const worklogUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${params!.issueKey?.trim() ?? ''}/worklog/${params!.worklogId?.trim() ?? ''}`
+        const worklogUrl = `https://api.atlassian.com/ex/jira/${cloudId}/rest/api/3/issue/${safeUrlPathSegment(params!.issueKey, 'issueKey')}/worklog/${safeUrlPathSegment(params!.worklogId, 'worklogId')}`
         const worklogResponse = await fetch(worklogUrl, {
           method: 'PUT',
           headers: {
diff --git a/apps/sim/tools/rootly/acknowledge_alert.ts b/apps/sim/tools/rootly/acknowledge_alert.ts
index a403ad7299a..1ae893314eb 100644
--- a/apps/sim/tools/rootly/acknowledge_alert.ts
+++ b/apps/sim/tools/rootly/acknowledge_alert.ts
@@ -3,6 +3,7 @@ import type {
   RootlyAcknowledgeAlertResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyAcknowledgeAlertTool: ToolConfig<
   RootlyAcknowledgeAlertParams,
@@ -29,7 +30,8 @@ export const rootlyAcknowledgeAlertTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/alerts/${params.alertId.trim()}/acknowledge`,
+    url: (params) =>
+      `https://api.rootly.com/v1/alerts/${safeUrlPathSegment(params.alertId, 'alertId')}/acknowledge`,
     method: 'POST',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/add_incident_event.ts b/apps/sim/tools/rootly/add_incident_event.ts
index cc9f1fe0ede..8d278ba15d7 100644
--- a/apps/sim/tools/rootly/add_incident_event.ts
+++ b/apps/sim/tools/rootly/add_incident_event.ts
@@ -3,6 +3,7 @@ import type {
   RootlyAddIncidentEventResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyAddIncidentEventTool: ToolConfig<
   RootlyAddIncidentEventParams,
@@ -41,7 +42,8 @@ export const rootlyAddIncidentEventTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/events`,
+    url: (params) =>
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/events`,
     method: 'POST',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/add_subscribers.ts b/apps/sim/tools/rootly/add_subscribers.ts
index 7035f013604..c3d92b2d4e8 100644
--- a/apps/sim/tools/rootly/add_subscribers.ts
+++ b/apps/sim/tools/rootly/add_subscribers.ts
@@ -1,5 +1,6 @@
 import type { RootlyAddSubscribersParams, RootlyIncidentActionResponse } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyAddSubscribersTool: ToolConfig<
   RootlyAddSubscribersParams,
@@ -33,7 +34,7 @@ export const rootlyAddSubscribersTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/add_subscribers`,
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/add_subscribers`,
     method: 'POST',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/assign_incident_role.ts b/apps/sim/tools/rootly/assign_incident_role.ts
index d016eaca5d8..488854000f8 100644
--- a/apps/sim/tools/rootly/assign_incident_role.ts
+++ b/apps/sim/tools/rootly/assign_incident_role.ts
@@ -3,6 +3,7 @@ import type {
   RootlyIncidentActionResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyAssignIncidentRoleTool: ToolConfig<
   RootlyAssignIncidentRoleParams,
@@ -42,7 +43,7 @@ export const rootlyAssignIncidentRoleTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/assign_role_to_user`,
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/assign_role_to_user`,
     method: 'POST',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/create_action_item.ts b/apps/sim/tools/rootly/create_action_item.ts
index 7297d19860f..2688230b4ba 100644
--- a/apps/sim/tools/rootly/create_action_item.ts
+++ b/apps/sim/tools/rootly/create_action_item.ts
@@ -3,6 +3,7 @@ import type {
   RootlyCreateActionItemResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyCreateActionItemTool: ToolConfig<
   RootlyCreateActionItemParams,
@@ -71,7 +72,8 @@ export const rootlyCreateActionItemTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/action_items`,
+    url: (params) =>
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/action_items`,
     method: 'POST',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/create_status_page_event.ts b/apps/sim/tools/rootly/create_status_page_event.ts
index d1506679024..3d186eba8a3 100644
--- a/apps/sim/tools/rootly/create_status_page_event.ts
+++ b/apps/sim/tools/rootly/create_status_page_event.ts
@@ -3,6 +3,7 @@ import type {
   RootlyCreateStatusPageEventResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyCreateStatusPageEventTool: ToolConfig<
   RootlyCreateStatusPageEventParams,
@@ -61,7 +62,7 @@ export const rootlyCreateStatusPageEventTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/status-page-events`,
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/status-page-events`,
     method: 'POST',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/delete_action_item.ts b/apps/sim/tools/rootly/delete_action_item.ts
index 055b2a4d594..c0f7e3d174b 100644
--- a/apps/sim/tools/rootly/delete_action_item.ts
+++ b/apps/sim/tools/rootly/delete_action_item.ts
@@ -3,6 +3,7 @@ import type {
   RootlyDeleteActionItemResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyDeleteActionItemTool: ToolConfig<
   RootlyDeleteActionItemParams,
@@ -29,7 +30,8 @@ export const rootlyDeleteActionItemTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/action_items/${params.actionItemId.trim()}`,
+    url: (params) =>
+      `https://api.rootly.com/v1/action_items/${safeUrlPathSegment(params.actionItemId, 'actionItemId')}`,
     method: 'DELETE',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/delete_incident.ts b/apps/sim/tools/rootly/delete_incident.ts
index 2b3a4cd0e80..32910ddac90 100644
--- a/apps/sim/tools/rootly/delete_incident.ts
+++ b/apps/sim/tools/rootly/delete_incident.ts
@@ -1,5 +1,6 @@
 import type { RootlyDeleteIncidentParams, RootlyDeleteIncidentResponse } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyDeleteIncidentTool: ToolConfig<
   RootlyDeleteIncidentParams,
@@ -26,7 +27,8 @@ export const rootlyDeleteIncidentTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}`,
+    url: (params) =>
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}`,
     method: 'DELETE',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/escalate_alert.ts b/apps/sim/tools/rootly/escalate_alert.ts
index 33d806abb07..7b6c3242475 100644
--- a/apps/sim/tools/rootly/escalate_alert.ts
+++ b/apps/sim/tools/rootly/escalate_alert.ts
@@ -1,5 +1,6 @@
 import type { RootlyAlertActionResponse, RootlyEscalateAlertParams } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyEscalateAlertTool: ToolConfig<
   RootlyEscalateAlertParams,
@@ -38,7 +39,8 @@ export const rootlyEscalateAlertTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/alerts/${params.alertId.trim()}/escalate`,
+    url: (params) =>
+      `https://api.rootly.com/v1/alerts/${safeUrlPathSegment(params.alertId, 'alertId')}/escalate`,
     method: 'POST',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/get_alert.ts b/apps/sim/tools/rootly/get_alert.ts
index 3b148219fb1..940d02bc15b 100644
--- a/apps/sim/tools/rootly/get_alert.ts
+++ b/apps/sim/tools/rootly/get_alert.ts
@@ -1,5 +1,6 @@
 import type { RootlyGetAlertParams, RootlyGetAlertResponse } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyGetAlertTool: ToolConfig<RootlyGetAlertParams, RootlyGetAlertResponse> = {
   id: 'rootly_get_alert',
@@ -23,7 +24,8 @@ export const rootlyGetAlertTool: ToolConfig<RootlyGetAlertParams, RootlyGetAlert
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/alerts/${params.alertId.trim()}`,
+    url: (params) =>
+      `https://api.rootly.com/v1/alerts/${safeUrlPathSegment(params.alertId, 'alertId')}`,
     method: 'GET',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/get_incident.ts b/apps/sim/tools/rootly/get_incident.ts
index 70b4f6c0f6d..9744630bc29 100644
--- a/apps/sim/tools/rootly/get_incident.ts
+++ b/apps/sim/tools/rootly/get_incident.ts
@@ -1,5 +1,6 @@
 import type { RootlyGetIncidentParams, RootlyGetIncidentResponse } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyGetIncidentTool: ToolConfig<RootlyGetIncidentParams, RootlyGetIncidentResponse> =
   {
@@ -24,7 +25,8 @@ export const rootlyGetIncidentTool: ToolConfig<RootlyGetIncidentParams, RootlyGe
     },
 
     request: {
-      url: (params) => `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}`,
+      url: (params) =>
+        `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}`,
       method: 'GET',
       headers: (params) => ({
         'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/list_action_items.ts b/apps/sim/tools/rootly/list_action_items.ts
index 96eb804c97a..2c1d16c7264 100644
--- a/apps/sim/tools/rootly/list_action_items.ts
+++ b/apps/sim/tools/rootly/list_action_items.ts
@@ -3,6 +3,7 @@ import type {
   RootlyListActionItemsResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyListActionItemsTool: ToolConfig<
   RootlyListActionItemsParams,
@@ -46,7 +47,7 @@ export const rootlyListActionItemsTool: ToolConfig<
       if (params.pageSize) queryParams.set('page[size]', String(params.pageSize))
       if (params.pageNumber) queryParams.set('page[number]', String(params.pageNumber))
       const qs = queryParams.toString()
-      return `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/action_items${qs ? `?${qs}` : ''}`
+      return `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/action_items${qs ? `?${qs}` : ''}`
     },
     method: 'GET',
     headers: (params) => ({
diff --git a/apps/sim/tools/rootly/list_incident_events.ts b/apps/sim/tools/rootly/list_incident_events.ts
index 2e85a36b4cf..031f1b2e63e 100644
--- a/apps/sim/tools/rootly/list_incident_events.ts
+++ b/apps/sim/tools/rootly/list_incident_events.ts
@@ -3,6 +3,7 @@ import type {
   RootlyListIncidentEventsResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyListIncidentEventsTool: ToolConfig<
   RootlyListIncidentEventsParams,
@@ -46,7 +47,7 @@ export const rootlyListIncidentEventsTool: ToolConfig<
       if (params.pageSize) queryParams.set('page[size]', String(params.pageSize))
       if (params.pageNumber) queryParams.set('page[number]', String(params.pageNumber))
       const qs = queryParams.toString()
-      return `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/events${qs ? `?${qs}` : ''}`
+      return `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/events${qs ? `?${qs}` : ''}`
     },
     method: 'GET',
     headers: (params) => ({
diff --git a/apps/sim/tools/rootly/mitigate_incident.ts b/apps/sim/tools/rootly/mitigate_incident.ts
index 16aca28e5ef..8b57c4c284e 100644
--- a/apps/sim/tools/rootly/mitigate_incident.ts
+++ b/apps/sim/tools/rootly/mitigate_incident.ts
@@ -3,6 +3,7 @@ import type {
   RootlyMitigateIncidentParams,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyMitigateIncidentTool: ToolConfig<
   RootlyMitigateIncidentParams,
@@ -35,7 +36,8 @@ export const rootlyMitigateIncidentTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/mitigate`,
+    url: (params) =>
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/mitigate`,
     method: 'PUT',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/path_safety.test.ts b/apps/sim/tools/rootly/path_safety.test.ts
new file mode 100644
index 00000000000..0852a5e49af
--- /dev/null
+++ b/apps/sim/tools/rootly/path_safety.test.ts
@@ -0,0 +1,216 @@
+/**
+ * @vitest-environment node
+ *
+ * Guards every Rootly tool against path traversal through an LLM-writable ID
+ * that gets interpolated into the request path.
+ *
+ * Incident, alert, action-item, and workflow IDs are `visibility: 'user-or-llm'`,
+ * so prompt injection controls them. Interpolating one raw let a value like
+ * `../../users/victim` escape its API prefix once `fetch` normalized the URL,
+ * re-aiming the request — and the workspace's Rootly bearer token — at an
+ * arbitrary Rootly resource, including on DELETE.
+ * `assertRequestUrlMatchesTrust` in `tools/request-transport.ts` only applies
+ * its canonicalization guard to internal `/api/` routes, so nothing downstream
+ * catches this.
+ *
+ * Wrapping the ID in `encodeURIComponent` is NOT enough, which is why the
+ * vector list below includes the bare `.` and `..` segments: both are made of
+ * unreserved characters, so they survive encoding untouched and the URL parser
+ * then removes them as dot segments, popping one path segment off a fixed host.
+ * Every assertion here resolves the built URL with `new URL(...)` — the same
+ * normalization `fetch` performs — rather than string-matching the template
+ * output, because string matching is exactly what let this through.
+ *
+ * The suite enumerates the tool barrel and then, per tool, every declared
+ * parameter that reaches a path segment, fuzzing **one parameter at a time**
+ * while the others hold a safe value. A new tool — or a new ID parameter on an
+ * existing tool — is therefore covered without anyone remembering to register
+ * it, and a still-guarded sibling parameter cannot mask an unguarded one by
+ * throwing first.
+ *
+ * Discovery inspects what `request.url` returns. That is total for this
+ * service: no Rootly tool issues a `fetch` of its own from `transformResponse`,
+ * so `request.url` is the only place a URL is built. Jira does build a second
+ * URL there, and its suite carries an extra block for it — if a Rootly tool
+ * ever grows one, this file needs the same.
+ */
+import { describe, expect, it } from 'vitest'
+import * as rootlyTools from '@/tools/rootly/index'
+
+/**
+ * The bare `.` and `..` entries are the whole point: their omission is why an
+ * `encodeURIComponent`-only fix looks correct while the hole stays live.
+ */
+const TRAVERSAL_IDS = [
+  '..',
+  '.',
+  '  ..  ',
+  '../../users/victim',
+  '..%2f..%2fusers/victim',
+  '123/../../../users/victim',
+  '123?injectedProbe=attacker',
+  '123#fragment',
+  '123/events/../../../workflows',
+  '\\..\\..',
+] as const
+
+/** Values a real user legitimately supplies; none may be rejected or altered. */
+const LEGITIMATE_IDS = [
+  '4f1c2b3a-5d6e-4f70-8a91-b2c3d4e5f607',
+  '00000000-0000-4000-8000-000000000000',
+  '12345',
+  'INC-42',
+  'incident_abc123',
+  'v1.2.3',
+  '..foo',
+  'foo..',
+] as const
+
+const SAFE_ID = 'SAFEID'
+
+/** Sentinel for the one parameter under test, so its slots are identifiable. */
+const PROBE_ID = 'PROBEID'
+
+const BASE_ORIGIN = 'https://api.rootly.com'
+
+/** Supplied by the platform, never by the model. */
+const FIXED_PARAMS: Record<string, unknown> = { apiKey: 'token' }
+
+/**
+ * The slice of a tool this suite drives. Narrowing to it — rather than reaching
+ * for `ToolConfig<any, any>` and an `as any` at the call site — keeps the
+ * harness typed end to end while staying agnostic about each tool's own param
+ * and response generics, which differ per tool and are irrelevant here.
+ */
+type ToolParams = Record<string, unknown>
+
+type UrlBuilder = (params: ToolParams) => string
+
+interface ParamDefinition {
+  readonly type?: string
+}
+
+interface PathBuildingTool {
+  readonly id: string
+  readonly params: Readonly<Record<string, ParamDefinition>>
+  readonly buildUrl: UrlBuilder
+}
+
+/**
+ * Narrows a barrel export to a Rootly tool that builds its URL from params.
+ * Anything else — a type-only re-export, a tool with a static URL — yields
+ * `null` and drops out of the suite.
+ */
+function asPathBuildingTool(value: unknown): PathBuildingTool | null {
+  if (typeof value !== 'object' || value === null) return null
+
+  const candidate = value as { id?: unknown; params?: unknown; request?: unknown }
+  if (typeof candidate.id !== 'string' || !candidate.id.startsWith('rootly_')) return null
+
+  const request = candidate.request as { url?: unknown } | undefined
+  if (typeof request?.url !== 'function') return null
+
+  return {
+    id: candidate.id,
+    params: (candidate.params ?? {}) as Record<string, ParamDefinition>,
+    buildUrl: request.url as UrlBuilder,
+  }
+}
+
+/**
+ * Fills every declared parameter with a type-appropriate safe value, then
+ * overrides the single parameter under test.
+ */
+function buildParams(tool: PathBuildingTool, paramName: string, value: string): ToolParams {
+  const params: ToolParams = {}
+  for (const [name, definition] of Object.entries(tool.params)) {
+    if (definition.type === 'json' || definition.type === 'array') {
+      params[name] = []
+    } else if (definition.type === 'number') {
+      params[name] = 1
+    } else if (definition.type === 'boolean') {
+      params[name] = false
+    } else {
+      params[name] = SAFE_ID
+    }
+  }
+  Object.assign(params, FIXED_PARAMS)
+  params[paramName] = value
+  return params
+}
+
+function buildUrl(tool: PathBuildingTool, paramName: string, value: string): URL {
+  return new URL(tool.buildUrl(buildParams(tool, paramName, value)))
+}
+
+function segmentsOf(tool: PathBuildingTool, paramName: string, value: string): string[] {
+  return buildUrl(tool, paramName, value).pathname.split('/')
+}
+
+/** Every (tool, parameter) pair whose value lands in a URL path segment. */
+const PATH_PARAMS = Object.values(rootlyTools)
+  .map(asPathBuildingTool)
+  .filter((tool): tool is PathBuildingTool => tool !== null)
+  .flatMap((tool) =>
+    Object.keys(tool.params)
+      .filter((name) => !(name in FIXED_PARAMS))
+      .filter((name) => {
+        try {
+          return buildUrl(tool, name, PROBE_ID).pathname.includes(PROBE_ID)
+        } catch {
+          return false
+        }
+      })
+      .map((name) => ({ label: `${tool.id} :: ${name}`, tool, paramName: name }))
+  )
+
+describe('rootly path-ID traversal safety', () => {
+  it('covers every Rootly parameter that reaches a URL path segment', () => {
+    expect(PATH_PARAMS.length).toBeGreaterThanOrEqual(23)
+  })
+
+  describe.each(PATH_PARAMS)('$label', ({ tool, paramName }) => {
+    const baseline = segmentsOf(tool, paramName, PROBE_ID)
+
+    it.each(TRAVERSAL_IDS)('cannot reshape the path with %j', (value) => {
+      let url: URL
+      try {
+        url = buildUrl(tool, paramName, value)
+      } catch {
+        return
+      }
+
+      expect(url.origin).toBe(BASE_ORIGIN)
+
+      const actual = url.pathname.split('/')
+      expect(actual).toHaveLength(baseline.length)
+      baseline.forEach((segment, index) => {
+        if (segment.includes(PROBE_ID)) return
+        expect(actual[index]).toBe(segment)
+      })
+    })
+
+    it.each(['..', '.'] as const)('rejects the bare %j segment by name', (value) => {
+      expect(() => buildUrl(tool, paramName, value)).toThrow(new RegExp(paramName))
+    })
+
+    it.each(LEGITIMATE_IDS)('passes %j through unchanged', (value) => {
+      const actual = segmentsOf(tool, paramName, value)
+
+      expect(actual).toHaveLength(baseline.length)
+      baseline.forEach((segment, index) => {
+        expect(actual[index]).toBe(segment.split(PROBE_ID).join(value))
+      })
+    })
+
+    it('trims surrounding whitespace without altering the id', () => {
+      expect(segmentsOf(tool, paramName, `  ${PROBE_ID}  `)).toEqual(baseline)
+    })
+
+    it('does not let the id inject a query parameter', () => {
+      const url = buildUrl(tool, paramName, `${PROBE_ID}?injectedProbe=attacker`)
+
+      expect(url.searchParams.get('injectedProbe')).toBeNull()
+    })
+  })
+})
diff --git a/apps/sim/tools/rootly/remove_subscribers.ts b/apps/sim/tools/rootly/remove_subscribers.ts
index 86b9bdc73f9..98d3bcccc2d 100644
--- a/apps/sim/tools/rootly/remove_subscribers.ts
+++ b/apps/sim/tools/rootly/remove_subscribers.ts
@@ -3,6 +3,7 @@ import type {
   RootlyRemoveSubscribersParams,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyRemoveSubscribersTool: ToolConfig<
   RootlyRemoveSubscribersParams,
@@ -36,7 +37,7 @@ export const rootlyRemoveSubscribersTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/remove_subscribers`,
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/remove_subscribers`,
     method: 'DELETE',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/resolve_alert.ts b/apps/sim/tools/rootly/resolve_alert.ts
index 550dc61ceed..b4d4f160897 100644
--- a/apps/sim/tools/rootly/resolve_alert.ts
+++ b/apps/sim/tools/rootly/resolve_alert.ts
@@ -1,5 +1,6 @@
 import type { RootlyResolveAlertParams, RootlyResolveAlertResponse } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyResolveAlertTool: ToolConfig<
   RootlyResolveAlertParams,
@@ -38,7 +39,8 @@ export const rootlyResolveAlertTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/alerts/${params.alertId.trim()}/resolve`,
+    url: (params) =>
+      `https://api.rootly.com/v1/alerts/${safeUrlPathSegment(params.alertId, 'alertId')}/resolve`,
     method: 'POST',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/resolve_incident.ts b/apps/sim/tools/rootly/resolve_incident.ts
index a6f4406ba3c..e85622a171f 100644
--- a/apps/sim/tools/rootly/resolve_incident.ts
+++ b/apps/sim/tools/rootly/resolve_incident.ts
@@ -3,6 +3,7 @@ import type {
   RootlyResolveIncidentParams,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyResolveIncidentTool: ToolConfig<
   RootlyResolveIncidentParams,
@@ -35,7 +36,8 @@ export const rootlyResolveIncidentTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/resolve`,
+    url: (params) =>
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/resolve`,
     method: 'PUT',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/run_workflow.ts b/apps/sim/tools/rootly/run_workflow.ts
index f37fbd8d73e..adff5841c34 100644
--- a/apps/sim/tools/rootly/run_workflow.ts
+++ b/apps/sim/tools/rootly/run_workflow.ts
@@ -1,5 +1,6 @@
 import type { RootlyRunWorkflowParams, RootlyRunWorkflowResponse } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyRunWorkflowTool: ToolConfig<RootlyRunWorkflowParams, RootlyRunWorkflowResponse> =
   {
@@ -50,7 +51,7 @@ export const rootlyRunWorkflowTool: ToolConfig<RootlyRunWorkflowParams, RootlyRu
 
     request: {
       url: (params) =>
-        `https://api.rootly.com/v1/workflows/${params.workflowId.trim()}/workflow_runs`,
+        `https://api.rootly.com/v1/workflows/${safeUrlPathSegment(params.workflowId, 'workflowId')}/workflow_runs`,
       method: 'POST',
       headers: (params) => ({
         'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/snooze_alert.ts b/apps/sim/tools/rootly/snooze_alert.ts
index 339cd1440a6..4c83c4aaab9 100644
--- a/apps/sim/tools/rootly/snooze_alert.ts
+++ b/apps/sim/tools/rootly/snooze_alert.ts
@@ -1,5 +1,6 @@
 import type { RootlyAlertActionResponse, RootlySnoozeAlertParams } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlySnoozeAlertTool: ToolConfig<RootlySnoozeAlertParams, RootlyAlertActionResponse> =
   {
@@ -30,7 +31,8 @@ export const rootlySnoozeAlertTool: ToolConfig<RootlySnoozeAlertParams, RootlyAl
     },
 
     request: {
-      url: (params) => `https://api.rootly.com/v1/alerts/${params.alertId.trim()}/snooze`,
+      url: (params) =>
+        `https://api.rootly.com/v1/alerts/${safeUrlPathSegment(params.alertId, 'alertId')}/snooze`,
       method: 'POST',
       headers: (params) => ({
         'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/unassign_incident_role.ts b/apps/sim/tools/rootly/unassign_incident_role.ts
index cc977939807..3de05111fc8 100644
--- a/apps/sim/tools/rootly/unassign_incident_role.ts
+++ b/apps/sim/tools/rootly/unassign_incident_role.ts
@@ -3,6 +3,7 @@ import type {
   RootlyUnassignIncidentRoleParams,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyUnassignIncidentRoleTool: ToolConfig<
   RootlyUnassignIncidentRoleParams,
@@ -42,7 +43,7 @@ export const rootlyUnassignIncidentRoleTool: ToolConfig<
 
   request: {
     url: (params) =>
-      `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}/unassign_role_from_user`,
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}/unassign_role_from_user`,
     method: 'DELETE',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/update_action_item.ts b/apps/sim/tools/rootly/update_action_item.ts
index df8a5e3cb57..bbdf82c907d 100644
--- a/apps/sim/tools/rootly/update_action_item.ts
+++ b/apps/sim/tools/rootly/update_action_item.ts
@@ -3,6 +3,7 @@ import type {
   RootlyUpdateActionItemResponse,
 } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyUpdateActionItemTool: ToolConfig<
   RootlyUpdateActionItemParams,
@@ -71,7 +72,8 @@ export const rootlyUpdateActionItemTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/action_items/${params.actionItemId.trim()}`,
+    url: (params) =>
+      `https://api.rootly.com/v1/action_items/${safeUrlPathSegment(params.actionItemId, 'actionItemId')}`,
     method: 'PUT',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/update_alert.ts b/apps/sim/tools/rootly/update_alert.ts
index ac64a2dffd2..b467c4ba1fa 100644
--- a/apps/sim/tools/rootly/update_alert.ts
+++ b/apps/sim/tools/rootly/update_alert.ts
@@ -1,5 +1,6 @@
 import type { RootlyUpdateAlertParams, RootlyUpdateAlertResponse } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyUpdateAlertTool: ToolConfig<RootlyUpdateAlertParams, RootlyUpdateAlertResponse> =
   {
@@ -78,7 +79,8 @@ export const rootlyUpdateAlertTool: ToolConfig<RootlyUpdateAlertParams, RootlyUp
     },
 
     request: {
-      url: (params) => `https://api.rootly.com/v1/alerts/${params.alertId.trim()}`,
+      url: (params) =>
+        `https://api.rootly.com/v1/alerts/${safeUrlPathSegment(params.alertId, 'alertId')}`,
       method: 'PATCH',
       headers: (params) => ({
         'Content-Type': 'application/vnd.api+json',
diff --git a/apps/sim/tools/rootly/update_incident.ts b/apps/sim/tools/rootly/update_incident.ts
index bebaf6f84e0..45377ade5c5 100644
--- a/apps/sim/tools/rootly/update_incident.ts
+++ b/apps/sim/tools/rootly/update_incident.ts
@@ -1,5 +1,6 @@
 import type { RootlyUpdateIncidentParams, RootlyUpdateIncidentResponse } from '@/tools/rootly/types'
 import type { ToolConfig } from '@/tools/types'
+import { safeUrlPathSegment } from '@/tools/url-path'
 
 export const rootlyUpdateIncidentTool: ToolConfig<
   RootlyUpdateIncidentParams,
@@ -118,7 +119,8 @@ export const rootlyUpdateIncidentTool: ToolConfig<
   },
 
   request: {
-    url: (params) => `https://api.rootly.com/v1/incidents/${params.incidentId.trim()}`,
+    url: (params) =>
+      `https://api.rootly.com/v1/incidents/${safeUrlPathSegment(params.incidentId, 'incidentId')}`,
     method: 'PUT',
     headers: (params) => ({
       'Content-Type': 'application/vnd.api+json',