diff --git a/apps/silo/src/apps/github/workers/github/event-handlers/issue-comment.handler.ts b/apps/silo/src/apps/github/workers/github/event-handlers/issue-comment.handler.ts
index 133377cb1c..d0170f463b 100644
--- a/apps/silo/src/apps/github/workers/github/event-handlers/issue-comment.handler.ts
+++ b/apps/silo/src/apps/github/workers/github/event-handlers/issue-comment.handler.ts
@@ -22,15 +22,16 @@ export type GithubCommentWebhookPayload = GithubWebhookPayload[
 };
 
 export const handleIssueComment = async (store: Store, action: GithubCommentAction, data: unknown) => {
+  // Check if this webhook was triggered by our own Plane->GitHub sync (loop prevention)
   // @ts-expect-error
   if (data && data.comment && data.comment.id) {
     // @ts-expect-error
-    const exist = await store.get(`silo:comment:${data.comment.id}`);
+    const exist = await store.get(`silo:comment:gh:${data.comment.id}`);
     if (exist) {
-      logger.info(`[ISSUE-COMMENT] Event Processed Successfully, confirmed by target`);
-      // Remove the webhook from the store
+      logger.info(`[ISSUE-COMMENT] Event triggered by Plane->GitHub sync, skipping to prevent loop`);
+      // Remove the key so future legitimate webhooks are not blocked
       // @ts-expect-error
-      await store.del(`silo:comment:${data.comment.id}`);
+      await store.del(`silo:comment:gh:${data.comment.id}`);
       return true;
     }
   }
@@ -169,7 +170,9 @@ export const syncCommentWithPlane = async (
       comment.id,
       planeComment
     );
-    await store.set(`silo:comment:${comment.id}`, "true");
+    // Set key with Plane comment ID so Plane->GitHub handler can detect and skip
+    // Use 5 second TTL to allow the webhook loop back but expire quickly
+    await store.set(`silo:comment:plane:${comment.id}`, "true", 5);
   } else {
     const createdComment = await planeClient.issueComment.create(
       workspaceConnection.workspace_slug,
@@ -177,7 +180,9 @@ export const syncCommentWithPlane = async (
       issue.id,
       planeComment
     );
-    await store.set(`silo:comment:${createdComment.id}`, "true");
+    // Set key with Plane comment ID so Plane->GitHub handler can detect and skip
+    // Use 5 second TTL to allow the webhook loop back but expire quickly
+    await store.set(`silo:comment:plane:${createdComment.id}`, "true", 5);
   }
 };
 
diff --git a/apps/silo/src/apps/github/workers/github/event-handlers/issue.handler.ts b/apps/silo/src/apps/github/workers/github/event-handlers/issue.handler.ts
index 43a35aef3d..30b9b0dec4 100644
--- a/apps/silo/src/apps/github/workers/github/event-handlers/issue.handler.ts
+++ b/apps/silo/src/apps/github/workers/github/event-handlers/issue.handler.ts
@@ -18,16 +18,17 @@ import type { Store } from "@/worker/base";
 const SYNC_LABEL = "plane";
 
 export const handleIssueEvents = async (store: Store, action: string, data: unknown) => {
-  // If the issue number exist inside the store, skip it
+  // Check if this webhook was triggered by our own Plane->GitHub sync (loop prevention)
+  // The Plane->GitHub handler sets a temporary key right after syncing to GitHub
   // @ts-expect-error
   if (data && data.issueNumber) {
     // @ts-expect-error
-    const exist = await store.get(`silo:issue:${data.issueNumber}`);
+    const exist = await store.get(`silo:issue:gh:${data.issueNumber}`);
     if (exist) {
-      logger.info(`[GITHUB][ISSUE] Event Processed Successfully, confirmed by target`);
-      // Remove the webhook from the store
+      logger.info(`[GITHUB][ISSUE] Event triggered by Plane->GitHub sync, skipping to prevent loop`);
+      // Remove the key so future legitimate webhooks are not blocked
       // @ts-expect-error
-      await store.del(`silo:issue:${data.issueNumber}`);
+      await store.del(`silo:issue:gh:${data.issueNumber}`);
       return true;
     }
   }
@@ -205,7 +206,9 @@ export const syncIssueWithPlane = async (store: Store, action: IssueWebhookActio
         issue.id,
         planeIssue
       );
-      await store.set(`silo:issue:${issue.id}`, "true");
+      // Set key with Plane issue ID so Plane->GitHub handler can detect and skip
+      // Use 5 second TTL to allow the webhook loop back but expire quickly
+      await store.set(`silo:issue:plane:${issue.id}`, "true", 5);
     } else {
       const createdIssue = await planeClient.issue.create(
         entityConnection.workspace_slug,
@@ -241,7 +244,9 @@ export const syncIssueWithPlane = async (store: Store, action: IssueWebhookActio
         await ghService.createIssueComment(data.owner, data.repositoryName, Number(data.issueNumber), comment);
       };
 
-      await Promise.all([createLink(), createLinkBack(), store.set(`silo:issue:${createdIssue.id}`, "true")]);
+      // Set key with Plane issue ID so Plane->GitHub handler can detect and skip
+      // Use 5 second TTL to allow the webhook loop back but expire quickly
+      await Promise.all([createLink(), createLinkBack(), store.set(`silo:issue:plane:${createdIssue.id}`, "true", 5)]);
     }
   } catch (error) {
     logger.error("Error syncing issue with Plane", error);
diff --git a/apps/silo/src/apps/github/workers/plane/event-handlers/issue-comment.handler.ts b/apps/silo/src/apps/github/workers/plane/event-handlers/issue-comment.handler.ts
index 968dc0a538..8d24068f5a 100644
--- a/apps/silo/src/apps/github/workers/plane/event-handlers/issue-comment.handler.ts
+++ b/apps/silo/src/apps/github/workers/plane/event-handlers/issue-comment.handler.ts
@@ -23,14 +23,13 @@ export const handleIssueCommentWebhook = async (
 ) => {
   const payloadId = payload?.id ?? "";
 
-  // Store a key associated with the data in the store
-  // If the key is present, then we need to requeue all that task and process them again
+  // Check if this webhook was triggered by our own GitHub->Plane sync (loop prevention)
   if (payloadId) {
-    const exist = await store.get(`silo:comment:${payload.id}`);
+    const exist = await store.get(`silo:comment:plane:${payload.id}`);
     if (exist) {
-      logger.info("[PLANE][COMMENT] Event Processed Successfully, confirmed by target");
-      // Remove the webhook from the store
-      await store.del(`silo:comment:${payload.id}`);
+      logger.info("[PLANE][COMMENT] Event triggered by GitHub->Plane sync, skipping to prevent loop");
+      // Remove the key so future legitimate webhooks are not blocked
+      await store.del(`silo:comment:plane:${payload.id}`);
       return true;
     }
   }
@@ -130,7 +129,9 @@ const handleCommentSync = async (store: Store, payload: PlaneWebhookPayload) =>
       credentials,
       ghIntegrationKey
     );
-    await store.set(`silo:comment:${githubComment.data.id}`, "true");
+    // Set key with GitHub comment ID so GitHub->Plane handler can detect and skip
+    // Use 5 second TTL to allow the webhook loop back but expire quickly
+    await store.set(`silo:comment:gh:${githubComment.data.id}`, "true", 5);
 
     if (
       !comment.external_id ||
diff --git a/apps/silo/src/apps/github/workers/plane/event-handlers/issue.handler.ts b/apps/silo/src/apps/github/workers/plane/event-handlers/issue.handler.ts
index 101d8d2b6a..5a684fb165 100644
--- a/apps/silo/src/apps/github/workers/plane/event-handlers/issue.handler.ts
+++ b/apps/silo/src/apps/github/workers/plane/event-handlers/issue.handler.ts
@@ -20,13 +20,14 @@ const apiClient = getAPIClient();
 export const imagePrefix = encodeURI(env.SILO_API_BASE_URL + env.SILO_BASE_PATH + "/api/assets/github/");
 
 export const handleIssueWebhook = async (headers: TaskHeaders, mq: MQ, store: Store, payload: PlaneWebhookPayload) => {
-  // Check for the key in the store, if the key is present, then the issue is already synced
+  // Check if this webhook was triggered by our own GitHub->Plane sync (loop prevention)
+  // The GitHub->Plane handler sets a temporary key with the Plane issue ID
   if (payload && payload.id) {
-    const exist = await store.get(`silo:issue:${payload.id}`);
+    const exist = await store.get(`silo:issue:plane:${payload.id}`);
     if (exist) {
-      logger.info("[PLANE][ISSUE] Event Processed Successfully, confirmed by target");
-      // Remove the webhook from the store
-      await store.del(`silo:issue:${payload.id}`);
+      logger.info("[PLANE][ISSUE] Event triggered by GitHub->Plane sync, skipping to prevent loop");
+      // Remove the key so future legitimate webhooks are not blocked
+      await store.del(`silo:issue:plane:${payload.id}`);
       return true;
     }
   }
@@ -127,8 +128,9 @@ const handleIssueSync = async (store: Store, payload: PlaneWebhookPayload) => {
       await Promise.all([addExternalId(), createLink()]);
     }
 
-    // Add the issue number to the store
-    await store.set(`silo:issue:${githubIssue?.data.number}`, "true");
+    // Set key with GitHub issue number so GitHub->Plane handler can detect and skip
+    // Use 5 second TTL to allow the webhook loop back but expire quickly
+    await store.set(`silo:issue:gh:${githubIssue?.data.number}`, "true", 5);
   } catch (error) {
     logger.error("[Plane][Github] Error handling issue create/update event", {
       error,