diff --git a/packages/server/src/server/agent/providers/claude/agent.test.ts b/packages/server/src/server/agent/providers/claude/agent.test.ts
index d28ac910ac..d88d8105cf 100644
--- a/packages/server/src/server/agent/providers/claude/agent.test.ts
+++ b/packages/server/src/server/agent/providers/claude/agent.test.ts
@@ -3069,6 +3069,44 @@ describe("ClaudeAgentSession context window usage", () => {
     }
   });
 
+  test("reports the plan mode Claude enters on its own with EnterPlanMode", async () => {
+    // Claude Code announces a mode it switched to itself as a status message
+    // carrying the new permissionMode, right after the EnterPlanMode tool call.
+    const client = new ClaudeAgentClient({
+      logger,
+      queryFactory: createQueryFactoryForTurns([
+        [
+          { ...createInitMessage(), permissionMode: "acceptEdits" },
+          {
+            type: "system",
+            subtype: "status",
+            status: null,
+            permissionMode: "plan",
+            session_id: "session-1",
+          },
+          createSuccessResult(),
+        ],
+      ]),
+      resolveBinary: async () => "/test/claude/bin",
+    });
+    const session = await client.createSession({
+      provider: "claude",
+      cwd: process.cwd(),
+      modeId: "acceptEdits",
+    });
+
+    try {
+      const events = await collectStreamEvents(session, "enter plan mode");
+
+      expect(events).toContainEqual(
+        expect.objectContaining({ type: "mode_changed", currentModeId: "plan" }),
+      );
+      expect(await session.getCurrentMode()).toBe("plan");
+    } finally {
+      await session.close();
+    }
+  });
+
   test("a compaction abandoned mid-turn does not suppress the next compaction marker", async () => {
     // The first turn starts compacting and then ends without ever reaching a
     // compact_boundary, so the marker it opened is never resolved.
diff --git a/packages/server/src/server/agent/providers/claude/agent.ts b/packages/server/src/server/agent/providers/claude/agent.ts
index 10048356b1..7b16c030a4 100644
--- a/packages/server/src/server/agent/providers/claude/agent.ts
+++ b/packages/server/src/server/agent/providers/claude/agent.ts
@@ -4321,6 +4321,19 @@ class ClaudeAgentSession implements AgentSession {
       return;
     }
     if (message.subtype === "status") {
+      // Claude Code reports a mode it switched to on its own, such as entering
+      // plan mode with the EnterPlanMode tool, through the status message.
+      if (
+        isPermissionMode(message.permissionMode) &&
+        this.observePermissionMode(message.permissionMode)
+      ) {
+        events.push({
+          type: "mode_changed",
+          provider: "claude",
+          currentModeId: this.currentMode,
+          availableModes: this.availableModes,
+        });
+      }
       const status = toObjectRecord(message)?.status;
       if (status === "compacting") {
         this.compacting = true;
@@ -4632,10 +4645,7 @@ class ClaudeAgentSession implements AgentSession {
       notice = this.createClaudeSessionChangedNotice(existingSessionId, newSessionId);
     }
     this.availableModes = DEFAULT_MODES;
-    this.currentMode = message.permissionMode;
-    if (this.currentMode !== "plan") {
-      this.planResumeMode = this.currentMode;
-    }
+    this.observePermissionMode(message.permissionMode);
     this.persistence = null;
     if (message.model) {
       const normalizedRuntimeModel = normalizeClaudeRuntimeModelId(message.model);
@@ -4654,6 +4664,16 @@ class ClaudeAgentSession implements AgentSession {
     return { threadStartedSessionId, notice };
   }
 
+  /** Records a mode Claude Code reports, returning whether it differs from the current one. */
+  private observePermissionMode(mode: PermissionMode): boolean {
+    const changed = this.currentMode !== mode;
+    this.currentMode = mode;
+    if (mode !== "plan") {
+      this.planResumeMode = mode;
+    }
+    return changed;
+  }
+
   private readMissingResumedConversationError(message: SDKMessage): string | null {
     if (message.type !== "result" || message.subtype !== "error_during_execution") {
       return null;