diff --git a/server/src/__tests__/chat-channels.integration.test.ts b/server/src/__tests__/chat-channels.integration.test.ts
index e877cbe2e8..c94734cf22 100644
--- a/server/src/__tests__/chat-channels.integration.test.ts
+++ b/server/src/__tests__/chat-channels.integration.test.ts
@@ -59573,7 +59573,7 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
       expect(
         deliveries.every((delivery) => delivery.state === "processed"),
       ).toBe(true);
-    });
+    }, { timeout: 5_000 });
 
     const [conversation] = await db
       .select()
@@ -59601,7 +59601,7 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
     ).resolves.toMatchObject({ ok: true });
     expect(deferred).toHaveLength(1);
     await drainDeferred();
-    await vi.waitFor(() => expect(deferred).toHaveLength(1));
+    await vi.waitFor(() => expect(deferred).toHaveLength(1), { timeout: 5_000 });
     await drainDeferred();
     await vi.waitFor(async () => {
       await expect(
@@ -59627,7 +59627,7 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
           state: "filtered",
         },
       ]);
-    });
+    }, { timeout: 5_000 });
     await expect(
       db
         .select({ body: issueComments.body })
diff --git a/server/src/__tests__/documents-service.test.ts b/server/src/__tests__/documents-service.test.ts
index 92dd1f3217..1115d0251f 100644
--- a/server/src/__tests__/documents-service.test.ts
+++ b/server/src/__tests__/documents-service.test.ts
@@ -1,5 +1,5 @@
 import { randomUUID } from "node:crypto";
-import { afterAll, afterEach, beforeAll, describe, expect, it } from "vitest";
+import { afterAll, afterEach, beforeAll, describe, expect, it, vi } from "vitest";
 import {
   companies,
   createDb,
@@ -86,6 +86,37 @@ describeEmbeddedPostgres("documentService system issue documents", () => {
     return { issueId };
   }
 
+  it.each([
+    "issue_documents_company_issue_key_uq",
+    "issue_documents_document_uq",
+    "document_revisions_document_revision_uq",
+  ])("only translates document-key conflicts for %s", async (constraintName) => {
+    const { issueId } = await createIssueWithDocuments();
+    const failure = new Error("Failed query", {
+      cause: { code: "23505", constraint_name: constraintName },
+    });
+    const transaction = vi.spyOn(db, "transaction").mockRejectedValueOnce(failure);
+    try {
+      const result = svc.upsertIssueDocument({
+        issueId,
+        key: "plan",
+        format: "markdown",
+        body: "Updated plan",
+      });
+      if (constraintName === "issue_documents_company_issue_key_uq") {
+        await expect(result).rejects.toMatchObject({
+          status: 409,
+          message: "Document key already exists on this issue",
+          details: { key: "plan" },
+        });
+      } else {
+        await expect(result).rejects.toBe(failure);
+      }
+    } finally {
+      transaction.mockRestore();
+    }
+  });
+
   it("filters continuation summaries from default document lists and issue payload summaries", async () => {
     const { issueId } = await createIssueWithDocuments();
 
diff --git a/server/src/services/documents.ts b/server/src/services/documents.ts
index 35cc8e3a7e..1ee5dcc2f2 100644
--- a/server/src/services/documents.ts
+++ b/server/src/services/documents.ts
@@ -499,7 +499,7 @@ export function documentService(db: Db) {
           };
           });
         } catch (error) {
-          if (isUniqueViolation(error)) {
+          if (isUniqueViolation(error, "issue_documents_company_issue_key_uq")) {
             if (input.lockedDocumentStrategy === "create_new_document" && attempt < maxAttempts - 1) {
               continue;
             }