diff --git a/compat/poll/poll.c b/compat/poll/poll.c
index ea362b4a8e2340..cc61b2704c7bd4 100644
--- a/compat/poll/poll.c
+++ b/compat/poll/poll.c
@@ -504,7 +504,21 @@ poll (struct pollfd *pfd, nfds_t nfd, int timeout)
 	     bits for the "wrong" direction. */
 	  pfd[i].revents = win32_compute_revents (h, &sought);
 	  if (sought)
-	    handle_array[nhandles++] = h;
+	    {
+	      /*
+	       * MsgWaitForMultipleObjects() below waits on the handles
+	       * collected here plus the message queue implied by
+	       * QS_ALLINPUT, so at most MAXIMUM_WAIT_OBJECTS - 1 handles
+	       * fit. Refuse to collect more instead of writing past the
+	       * end of handle_array.
+	       */
+	      if (nhandles >= MAXIMUM_WAIT_OBJECTS - 1)
+		{
+		  errno = EINVAL;
+		  return -1;
+		}
+	      handle_array[nhandles++] = h;
+	    }
 	  if (pfd[i].revents)
 	    timeout = 0;
 	}
diff --git a/parallel-checkout.c b/parallel-checkout.c
index 1eb277a0fc0a55..5f27143d6cf532 100644
--- a/parallel-checkout.c
+++ b/parallel-checkout.c
@@ -41,6 +41,18 @@ enum pc_status parallel_checkout_status(void)
 static const int DEFAULT_THRESHOLD_FOR_PARALLELISM = 100;
 static const int DEFAULT_NUM_WORKERS = 1;
 
+#ifdef GIT_WINDOWS_NATIVE
+/*
+ * Windows has no native poll(). compat/poll emulates it with
+ * MsgWaitForMultipleObjects(), which waits on at most MAXIMUM_WAIT_OBJECTS
+ * objects. One of those is the message queue implied by QS_ALLINPUT, and
+ * compat/poll reserves another for its own event object, leaving room for
+ * MAXIMUM_WAIT_OBJECTS - 2 descriptors. gather_results_from_workers() polls
+ * one pipe per worker, so the worker count must stay within that limit.
+ */
+#define MAX_PARALLEL_CHECKOUT_WORKERS (MAXIMUM_WAIT_OBJECTS - 2)
+#endif
+
 void get_parallel_checkout_configs(int *num_workers, int *threshold)
 {
 	char *env_workers = getenv("GIT_TEST_CHECKOUT_WORKERS");
@@ -671,6 +683,11 @@ int run_parallel_checkout(struct checkout *state, int num_workers, int threshold
 	if (parallel_checkout.nr < num_workers)
 		num_workers = parallel_checkout.nr;
 
+#ifdef GIT_WINDOWS_NATIVE
+	if (num_workers > MAX_PARALLEL_CHECKOUT_WORKERS)
+		num_workers = MAX_PARALLEL_CHECKOUT_WORKERS;
+#endif
+
 	if (num_workers <= 1 || parallel_checkout.nr < threshold) {
 		write_items_sequentially(state);
 	} else {
diff --git a/t/t2080-parallel-checkout-basics.sh b/t/t2080-parallel-checkout-basics.sh
index 7ad96cd5cd24a3..cf0d822fd708de 100755
--- a/t/t2080-parallel-checkout-basics.sh
+++ b/t/t2080-parallel-checkout-basics.sh
@@ -320,4 +320,41 @@ test_expect_success MINGW 'parallel checkout with fscache does not fail on new d
 	)
 '
 
+# A worker count far above any platform limit must still produce a correct
+# checkout. On Windows this used to smash the stack, because compat/poll
+# collected one wait handle per polled worker pipe in a fixed-size array.
+#
+# This test does not verify that clamping happens, and it cannot easily do so:
+# the clamp is not reported anywhere, and the number of workers that are
+# actually pending inside poll() depends on timing and I/O state, so no
+# specific worker count reliably demonstrates the old failure either. All the
+# test asserts is that a high worker count succeeds.
+test_expect_success 'checkout with more workers than the platform can poll' '
+	test_when_finished "rm -rf many-workers-repo" &&
+	git init many-workers-repo &&
+	(
+		cd many-workers-repo &&
+		mkdir -p dir &&
+		for i in $(test_seq 1 200)
+		do
+			echo "content $i" >dir/file$i || return 1
+		done &&
+		git add -A &&
+		git commit -q -m base &&
+		git checkout -q -b other &&
+		for i in $(test_seq 1 200)
+		do
+			echo "changed $i" >dir/file$i || return 1
+		done &&
+		git commit -q -a -m changed &&
+
+		git config checkout.workers 200 &&
+		git config checkout.thresholdForParallelism 1 &&
+
+		git checkout -q - &&
+		git checkout -q other &&
+		test "$(cat dir/file1)" = "changed 1"
+	)
+'
+
 test_done