diff --git a/server/src/__tests__/document-annotation-routes.test.ts b/server/src/__tests__/document-annotation-routes.test.ts
index 3e5201d74cc..1fd64e02dc2 100644
--- a/server/src/__tests__/document-annotation-routes.test.ts
+++ b/server/src/__tests__/document-annotation-routes.test.ts
@@ -298,6 +298,10 @@ describe("document annotation routes", () => {
     expect(mockIssueReferenceService.syncAnnotationComment).toHaveBeenCalledWith(annotationComment.id);
     expect(mockLogActivity).toHaveBeenCalledWith(expect.anything(), expect.objectContaining({
       action: "issue.document_annotation_thread_created",
+      details: expect.objectContaining({
+        key: "plan",
+        documentKey: "plan",
+      }),
     }));
     expect(mockHeartbeatService.wakeup).not.toHaveBeenCalled();
   });
@@ -324,6 +328,10 @@ describe("document annotation routes", () => {
     expect(mockIssueReferenceService.syncAnnotationComment).toHaveBeenCalledWith(annotationComment.id);
     expect(mockLogActivity).toHaveBeenCalledWith(expect.anything(), expect.objectContaining({
       action: "issue.document_annotation_comment_added",
+      details: expect.objectContaining({
+        key: "plan",
+        documentKey: "plan",
+      }),
     }));
     expect(mockHeartbeatService.wakeup).not.toHaveBeenCalled();
 
@@ -334,6 +342,10 @@ describe("document annotation routes", () => {
     expect(resolved.body.status).toBe("resolved");
     expect(mockLogActivity).toHaveBeenCalledWith(expect.anything(), expect.objectContaining({
       action: "issue.document_annotation_thread_resolved",
+      details: expect.objectContaining({
+        key: "plan",
+        documentKey: "plan",
+      }),
     }));
     expect(mockHeartbeatService.wakeup).not.toHaveBeenCalled();
   });
diff --git a/server/src/routes/issues.ts b/server/src/routes/issues.ts
index 6ee09f0d079..090b6c7ffbd 100644
--- a/server/src/routes/issues.ts
+++ b/server/src/routes/issues.ts
@@ -3299,6 +3299,7 @@ export function issueRoutes(
         entityType: "issue",
         entityId: issue.id,
         details: {
+          key: thread.documentKey,
           documentKey: thread.documentKey,
           documentId: thread.documentId,
           threadId: thread.id,
@@ -3383,6 +3384,7 @@ export function issueRoutes(
         entityType: "issue",
         entityId: issue.id,
         details: {
+          key: keyParsed.data,
           documentKey: keyParsed.data,
           threadId: comment.threadId,
           commentId: comment.id,
@@ -3436,6 +3438,7 @@ export function issueRoutes(
         entityType: "issue",
         entityId: issue.id,
         details: {
+          key: thread.documentKey,
           documentKey: thread.documentKey,
           documentId: thread.documentId,
           threadId: thread.id,