diff --git a/src/index.ts b/src/index.ts
index 1c3ca77..27a3f2f 100755
--- a/src/index.ts
+++ b/src/index.ts
@@ -362,6 +362,16 @@ async function main(): Promise<void> {
     // Silently ignore update failures
   });
 
+  // Clean up old overflow files (non-blocking, 24h retention)
+  const { cleanupOldOverflowFiles } = await import("./tools/impl/overflow");
+  Promise.resolve().then(() => {
+    try {
+      cleanupOldOverflowFiles(process.cwd());
+    } catch {
+      // Silently ignore cleanup failures
+    }
+  });
+
   // Parse command-line arguments (Bun-idiomatic approach using parseArgs)
   // Preprocess args to support --conv as alias for --conversation
   const processedArgs = process.argv.map((arg) =>
diff --git a/src/tests/tools/overflow.test.ts b/src/tests/tools/overflow.test.ts
index 3c6959d..aa8cee4 100644
--- a/src/tests/tools/overflow.test.ts
+++ b/src/tests/tools/overflow.test.ts
@@ -170,6 +170,33 @@ describe("overflow utilities", () => {
 
       expect(deletedCount).toBe(0);
     });
+
+    test("skips subdirectories without crashing", () => {
+      // Create a test file and a subdirectory
+      const content = "Test content";
+      const filePath = writeOverflowFile(content, testWorkingDir, "TestTool");
+
+      // Create a subdirectory in the overflow dir
+      const subDir = path.join(path.dirname(filePath), "subdir");
+      fs.mkdirSync(subDir, { recursive: true });
+
+      // Make the file old
+      const oldTime = Date.now() - 48 * 60 * 60 * 1000;
+      fs.utimesSync(filePath, new Date(oldTime), new Date(oldTime));
+
+      // Cleanup should skip the directory and only delete the file
+      const deletedCount = cleanupOldOverflowFiles(
+        testWorkingDir,
+        24 * 60 * 60 * 1000,
+      );
+
+      expect(deletedCount).toBe(1);
+      expect(fs.existsSync(filePath)).toBe(false);
+      expect(fs.existsSync(subDir)).toBe(true);
+
+      // Clean up the subdir
+      fs.rmdirSync(subDir);
+    });
   });
 
   describe("getOverflowStats", () => {
diff --git a/src/tools/impl/Task.ts b/src/tools/impl/Task.ts
index 66b5ecc..828a00f 100644
--- a/src/tools/impl/Task.ts
+++ b/src/tools/impl/Task.ts
@@ -16,6 +16,7 @@ import {
   generateSubagentId,
   registerSubagent,
 } from "../../cli/helpers/subagentState.js";
+import { LIMITS, truncateByChars } from "./truncation.js";
 import { validateRequiredParams } from "./validation";
 
 interface TaskArgs {
@@ -114,7 +115,18 @@ export async function task(args: TaskArgs): Promise<string> {
       .filter(Boolean)
       .join(" ");
 
-    return `${header}\n\n${result.report}`;
+    const fullOutput = `${header}\n\n${result.report}`;
+    const userCwd = process.env.USER_CWD || process.cwd();
+
+    // Apply truncation to prevent excessive token usage (same pattern as Bash tool)
+    const { content: truncatedOutput } = truncateByChars(
+      fullOutput,
+      LIMITS.TASK_OUTPUT_CHARS,
+      "Task",
+      { workingDirectory: userCwd, toolName: "Task" },
+    );
+
+    return truncatedOutput;
   } catch (error) {
     const errorMessage = error instanceof Error ? error.message : String(error);
     completeSubagent(subagentId, { success: false, error: errorMessage });
diff --git a/src/tools/impl/overflow.ts b/src/tools/impl/overflow.ts
index 9c7959b..d345ffa 100644
--- a/src/tools/impl/overflow.ts
+++ b/src/tools/impl/overflow.ts
@@ -113,17 +113,33 @@ export function cleanupOldOverflowFiles(
     return 0;
   }
 
-  const files = fs.readdirSync(overflowDir);
+  let files: string[];
+  try {
+    files = fs.readdirSync(overflowDir);
+  } catch {
+    // Directory may have been deleted or become inaccessible
+    return 0;
+  }
+
   const now = Date.now();
   let deletedCount = 0;
 
   for (const file of files) {
     const filePath = path.join(overflowDir, file);
-    const stats = fs.statSync(filePath);
+    try {
+      const stats = fs.statSync(filePath);
 
-    if (now - stats.mtimeMs > maxAgeMs) {
-      fs.unlinkSync(filePath);
-      deletedCount++;
+      // Skip directories (shouldn't exist, but be safe)
+      if (stats.isDirectory()) {
+        continue;
+      }
+
+      if (now - stats.mtimeMs > maxAgeMs) {
+        fs.unlinkSync(filePath);
+        deletedCount++;
+      }
+    } catch {
+      // File may have been deleted, or permission error - skip it
     }
   }
 
diff --git a/src/tools/impl/truncation.ts b/src/tools/impl/truncation.ts
index 00e3360..0be2acd 100644
--- a/src/tools/impl/truncation.ts
+++ b/src/tools/impl/truncation.ts
@@ -10,6 +10,7 @@ import { OVERFLOW_CONFIG, writeOverflowFile } from "./overflow.js";
 export const LIMITS = {
   // Command output limits
   BASH_OUTPUT_CHARS: 30_000, // 30K characters for bash/shell output
+  TASK_OUTPUT_CHARS: 30_000, // 30K characters for subagent task output
 
   // File reading limits
   READ_MAX_LINES: 2_000, // Max lines per file read