diff --git a/extensions/cli/src/commands/serve.ts b/extensions/cli/src/commands/serve.ts
index f0a41469b3f..cefe2e6dd9b 100644
--- a/extensions/cli/src/commands/serve.ts
+++ b/extensions/cli/src/commands/serve.ts
@@ -529,7 +529,19 @@ export async function serve(prompt?: string, options: ServeOptions = {}) {
         // Update metadata after successful agent turn
         try {
           const history = services.chatHistory?.getHistory();
-          await updateAgentMetadata(history);
+
+          // Check if the agent should be marked as complete
+          // The agent is complete if the last message is from the assistant and has no tool calls
+          let isComplete = false;
+          if (history && history.length > 0) {
+            const lastItem = history[history.length - 1];
+            if (lastItem?.message?.role === "assistant") {
+              const toolCalls = (lastItem.message as any).tool_calls;
+              isComplete = !toolCalls || toolCalls.length === 0;
+            }
+          }
+
+          await updateAgentMetadata({ history, isComplete });
         } catch (metadataErr) {
           // Non-critical: log but don't fail the agent execution
           logger.debug(
diff --git a/extensions/cli/src/tools/exit.ts b/extensions/cli/src/tools/exit.ts
index a6d84bdc3ee..987b9522ecf 100644
--- a/extensions/cli/src/tools/exit.ts
+++ b/extensions/cli/src/tools/exit.ts
@@ -1,3 +1,5 @@
+import { logger } from "../util/logger.js";
+
 import { Tool } from "./types.js";
 
 export const exitTool: Tool = {
@@ -12,7 +14,21 @@ export const exitTool: Tool = {
   readonly: false,
   isBuiltIn: true,
   run: async (): Promise<string> => {
-    const { gracefulExit } = await import("../util/exit.js");
+    const { gracefulExit, updateAgentMetadata } = await import(
+      "../util/exit.js"
+    );
+
+    // Mark agent as complete before exiting
+    try {
+      await updateAgentMetadata({ isComplete: true });
+    } catch (err) {
+      // Non-critical: log but don't block exit
+      logger.debug(
+        "Failed to update completion metadata (non-critical)",
+        err as any,
+      );
+    }
+
     await gracefulExit(1);
     return "";
   },
diff --git a/extensions/cli/src/tools/reportFailure.ts b/extensions/cli/src/tools/reportFailure.ts
index 1e0fede2e65..a2d56fe3304 100644
--- a/extensions/cli/src/tools/reportFailure.ts
+++ b/extensions/cli/src/tools/reportFailure.ts
@@ -6,6 +6,7 @@ import {
   AuthenticationRequiredError,
   post,
 } from "../util/apiClient.js";
+import { updateAgentMetadata } from "../util/exit.js";
 import { logger } from "../util/logger.js";
 
 import { Tool } from "./types.js";
@@ -74,6 +75,18 @@ export const reportFailureTool: Tool = {
         errorMessage: trimmedMessage,
       });
 
+      // Mark agent as complete since it failed
+      try {
+        await updateAgentMetadata({ isComplete: true });
+        logger.debug("Marked agent as complete due to failure");
+      } catch (metadataErr) {
+        // Non-critical: log but don't fail the failure report
+        logger.debug(
+          "Failed to update completion metadata (non-critical)",
+          metadataErr as any,
+        );
+      }
+
       logger.info(`Failure reported: ${trimmedMessage}`);
       return "Failure reported to user.";
     } catch (error) {
diff --git a/extensions/cli/src/tools/status.ts b/extensions/cli/src/tools/status.ts
index c75eec837f6..c545a8d581d 100644
--- a/extensions/cli/src/tools/status.ts
+++ b/extensions/cli/src/tools/status.ts
@@ -5,6 +5,7 @@ import {
   AuthenticationRequiredError,
   post,
 } from "../util/apiClient.js";
+import { updateAgentMetadata } from "../util/exit.js";
 import { logger } from "../util/logger.js";
 
 import { Tool } from "./types.js";
@@ -62,6 +63,24 @@ You should use this tool to notify the user whenever the state of your work chan
       await post(`agents/${agentId}/status`, { status: args.status });
 
       logger.info(`Status: ${args.status}`);
+
+      // If status is DONE or FAILED, mark agent as complete
+      const normalizedStatus = args.status.toUpperCase();
+      if (normalizedStatus === "DONE" || normalizedStatus === "FAILED") {
+        try {
+          await updateAgentMetadata({ isComplete: true });
+          logger.debug(
+            `Marked agent as complete due to status: ${args.status}`,
+          );
+        } catch (metadataErr) {
+          // Non-critical: log but don't fail the status update
+          logger.debug(
+            "Failed to update completion metadata (non-critical)",
+            metadataErr as any,
+          );
+        }
+      }
+
       return `Status set: ${args.status}`;
     } catch (error) {
       if (error instanceof ContinueError) {