diff --git a/packages/cli/src/cli/agent-relay-mcp.startup.test.ts b/packages/cli/src/cli/agent-relay-mcp.startup.test.ts
index 94f664185..ebcca9f9b 100644
--- a/packages/cli/src/cli/agent-relay-mcp.startup.test.ts
+++ b/packages/cli/src/cli/agent-relay-mcp.startup.test.ts
@@ -593,6 +593,10 @@ describe('createAgentRelayMcpServer', () => {
     // `node up` mentioned it.
     expect(result.structuredContent.message).toContain('node_abc');
     expect(result.structuredContent.message).toContain('relay cloud enroll');
+    // A cleared enrollment means the write SUCCEEDED. Reporting it through the
+    // persistence-failure wording would tell the caller the key never landed.
+    expect(result.structuredContent.message).toContain('persisted for this project');
+    expect(result.structuredContent.message).not.toContain('could not be persisted');
   });
 
   it('registers submit_result when a spawned-agent result callback is configured', async () => {
diff --git a/packages/cli/src/cli/agent-relay-mcp.ts b/packages/cli/src/cli/agent-relay-mcp.ts
index d24af51b3..8ef54b2d6 100644
--- a/packages/cli/src/cli/agent-relay-mcp.ts
+++ b/packages/cli/src/cli/agent-relay-mcp.ts
@@ -499,11 +499,15 @@ function registerAgentRelayTools(
       } else {
         setSession({ workspaceKey: key });
       }
+      // Two distinct outcomes, never conflated: the write failed, or the write
+      // succeeded and dropped this project's enrolled fleet node. Reporting the
+      // second as the first would tell the caller the key had not persisted.
       let persistenceWarning: string | undefined;
+      let clearedEnrollmentWarning: string | undefined;
       try {
         // Joining a different workspace drops this project's enrolled fleet
         // node; surface that here instead of at the next `node up`.
-        persistenceWarning = describeClearedEnrollment(persistWorkspaceSession({ workspaceKey: key }));
+        clearedEnrollmentWarning = describeClearedEnrollment(persistWorkspaceSession({ workspaceKey: key }));
       } catch (error) {
         const persistenceError = error instanceof Error ? error.message : String(error);
         persistenceWarning =
@@ -517,7 +521,9 @@ function registerAgentRelayTools(
       const activeMessage = switchingWorkspace
         ? 'Workspace key set. Call "register_agent" to join this workspace.'
         : 'Workspace key set.';
-      const message = persistenceWarning ? `${activeMessage} ${persistenceWarning}` : persistedMessage;
+      const message = persistenceWarning
+        ? `${activeMessage} ${persistenceWarning}`
+        : [persistedMessage, clearedEnrollmentWarning].filter(Boolean).join(' ');
       return textContent(message);
     }
   );