diff --git a/packages/core/src/tools/glob.test.ts b/packages/core/src/tools/glob.test.ts
index e747a1eec8..30a932d49e 100644
--- a/packages/core/src/tools/glob.test.ts
+++ b/packages/core/src/tools/glob.test.ts
@@ -659,6 +659,25 @@ describe('GlobTool', () => {
       expect(result.llmContent).toContain('[5 files truncated] ...');
     });
   });
+
+  describe('getDefaultPermission', () => {
+    it('should return allow for paths within workspace', async () => {
+      const params: GlobToolParams = { pattern: '*', path: 'sub' };
+      const invocation = globTool.build(params);
+      const permission = await invocation.getDefaultPermission();
+      expect(permission).toBe('allow');
+    });
+
+    it('should return ask for tilde paths outside workspace', async () => {
+      const params: GlobToolParams = {
+        pattern: '*',
+        path: '~/outside-workspace',
+      };
+      const invocation = globTool.build(params);
+      const permission = await invocation.getDefaultPermission();
+      expect(permission).toBe('ask');
+    });
+  });
 });
 
 describe('sortFileEntries', () => {
diff --git a/packages/core/src/tools/glob.ts b/packages/core/src/tools/glob.ts
index 24cb661f8a..d68ecca59f 100644
--- a/packages/core/src/tools/glob.ts
+++ b/packages/core/src/tools/glob.ts
@@ -12,6 +12,7 @@ import { BaseDeclarativeTool, BaseToolInvocation, Kind } from './tools.js';
 import { ToolNames, ToolDisplayNames } from './tool-names.js';
 import {
   resolveAndValidatePath,
+  resolvePath,
   isSubpath,
   unescapePath,
 } from '../utils/paths.js';
@@ -114,7 +115,7 @@ class GlobToolInvocation extends BaseToolInvocation<
       return 'allow'; // Default workspace directory
     }
     const workspaceContext = this.config.getWorkspaceContext();
-    const resolvedPath = path.resolve(
+    const resolvedPath = resolvePath(
       this.config.getTargetDir(),
       this.params.path,
     );
diff --git a/packages/core/src/tools/grep.test.ts b/packages/core/src/tools/grep.test.ts
index 473efecf80..e3fcbe8419 100644
--- a/packages/core/src/tools/grep.test.ts
+++ b/packages/core/src/tools/grep.test.ts
@@ -597,6 +597,25 @@ describe('GrepTool', () => {
     });
   });
 
+  describe('getDefaultPermission', () => {
+    it('should return allow for paths within workspace', async () => {
+      const params: GrepToolParams = { pattern: 'hello', path: 'sub' };
+      const invocation = grepTool.build(params);
+      const permission = await invocation.getDefaultPermission();
+      expect(permission).toBe('allow');
+    });
+
+    it('should return ask for tilde paths outside workspace', async () => {
+      const params: GrepToolParams = {
+        pattern: 'hello',
+        path: '~/outside-workspace',
+      };
+      const invocation = grepTool.build(params);
+      const permission = await invocation.getDefaultPermission();
+      expect(permission).toBe('ask');
+    });
+  });
+
   describe('Result limiting', () => {
     beforeEach(async () => {
       // Create many test files with matches to test limiting
diff --git a/packages/core/src/tools/grep.ts b/packages/core/src/tools/grep.ts
index ae1fa2edea..d0d30712f5 100644
--- a/packages/core/src/tools/grep.ts
+++ b/packages/core/src/tools/grep.ts
@@ -15,6 +15,7 @@ import { ToolNames, ToolDisplayNames } from './tool-names.js';
 import { createDebugLogger } from '../utils/debugLogger.js';
 import {
   resolveAndValidatePath,
+  resolvePath,
   isSubpath,
   unescapePath,
 } from '../utils/paths.js';
@@ -91,7 +92,7 @@ class GrepToolInvocation extends BaseToolInvocation<
       return 'allow'; // Default workspace directory
     }
     const workspaceContext = this.config.getWorkspaceContext();
-    const resolvedPath = path.resolve(
+    const resolvedPath = resolvePath(
       this.config.getTargetDir(),
       this.params.path,
     );
diff --git a/packages/core/src/tools/ripGrep.test.ts b/packages/core/src/tools/ripGrep.test.ts
index ab4e4efe55..57b12e067a 100644
--- a/packages/core/src/tools/ripGrep.test.ts
+++ b/packages/core/src/tools/ripGrep.test.ts
@@ -1132,5 +1132,15 @@ describe('RipGrepTool', () => {
       const permission = await invocation.getDefaultPermission();
       expect(permission).toBe('ask');
     });
+
+    it('should return ask for tilde paths outside workspace', async () => {
+      const params: RipGrepToolParams = {
+        pattern: 'hello',
+        path: '~/outside-workspace',
+      };
+      const invocation = grepTool.build(params);
+      const permission = await invocation.getDefaultPermission();
+      expect(permission).toBe('ask');
+    });
   });
 });
diff --git a/packages/core/src/tools/ripGrep.ts b/packages/core/src/tools/ripGrep.ts
index 5faa6f95c7..34299d3b35 100644
--- a/packages/core/src/tools/ripGrep.ts
+++ b/packages/core/src/tools/ripGrep.ts
@@ -9,7 +9,11 @@ import path from 'node:path';
 import type { ToolInvocation, ToolResult } from './tools.js';
 import { BaseDeclarativeTool, BaseToolInvocation, Kind } from './tools.js';
 import { ToolNames } from './tool-names.js';
-import { resolveAndValidatePath, unescapePath } from '../utils/paths.js';
+import {
+  resolveAndValidatePath,
+  resolvePath,
+  unescapePath,
+} from '../utils/paths.js';
 import { getErrorMessage } from '../utils/errors.js';
 import type { Config } from '../config/config.js';
 import { runRipgrep } from '../utils/ripgrepUtils.js';
@@ -149,7 +153,7 @@ class GrepToolInvocation extends BaseToolInvocation<
       return 'allow'; // Default workspace directory
     }
     const workspaceContext = this.config.getWorkspaceContext();
-    const resolvedPath = path.resolve(
+    const resolvedPath = resolvePath(
       this.config.getTargetDir(),
       this.params.path,
     );