diff --git a/apps/desktop/src-tauri/src/core/built_in_tools/bash.rs b/apps/desktop/src-tauri/src/core/built_in_tools/bash.rs
index a467b154..32cba66c 100644
--- a/apps/desktop/src-tauri/src/core/built_in_tools/bash.rs
+++ b/apps/desktop/src-tauri/src/core/built_in_tools/bash.rs
@@ -96,6 +96,32 @@ async fn try_rtk_rewrite(command: &str) -> Option<String> {
     None
 }
 
+#[cfg(target_os = "windows")]
+fn validate_working_directory(
+    working_directory: Option<&str>,
+    allowed_directories: &[String],
+) -> Result<(), String> {
+    let Some(working_directory) = working_directory else {
+        return Ok(());
+    };
+    if allowed_directories.is_empty() {
+        return Ok(());
+    }
+
+    let canonical_working_directory = std::fs::canonicalize(working_directory)
+        .map_err(|error| format!("Failed to resolve working directory: {error}"))?;
+    let is_allowed = allowed_directories.iter().any(|allowed_directory| {
+        std::fs::canonicalize(allowed_directory)
+            .map(|canonical_allowed| canonical_working_directory.starts_with(canonical_allowed))
+            .unwrap_or(false)
+    });
+    if is_allowed {
+        Ok(())
+    } else {
+        Err("Working directory is outside the allowed scope".to_string())
+    }
+}
+
 #[cfg(target_os = "windows")]
 async fn execute_bash_windows(
     request: BuiltInBashExecutionRequest,
@@ -106,6 +132,11 @@ async fn execute_bash_windows(
         return Err("Command cannot be empty".to_string());
     }
 
+    validate_working_directory(
+        request.working_directory.as_deref(),
+        &request.allowed_working_directories,
+    )?;
+
     // 当输出压缩启用且模型未请求原始输出时，通过 rtk rewrite 判断命令是否可重写，
     // 支持的命令自动替换为 rtk 等价形式，不支持的原样执行。
     let (effective_command, compressed) =
@@ -257,3 +288,27 @@ fn build_powershell_command_script(command: &str) -> String {
         format!("{}\n{}\n{}", UTF8_POWERSHELL_PRELUDE, path_prelude, command)
     }
 }
+
+#[cfg(all(test, target_os = "windows"))]
+mod tests {
+    use super::validate_working_directory;
+    use std::fs;
+
+    #[test]
+    fn rejects_canonical_working_directory_outside_allowlist() {
+        let root = tempfile::tempdir().expect("tempdir");
+        let allowed = root.path().join("allowed");
+        let outside = root.path().join("outside");
+        fs::create_dir_all(&allowed).expect("allowed directory");
+        fs::create_dir_all(&outside).expect("outside directory");
+        let escaped = allowed.join("..").join("outside");
+
+        let error = validate_working_directory(
+            Some(escaped.to_string_lossy().as_ref()),
+            &[allowed.to_string_lossy().into_owned()],
+        )
+        .expect_err("escaped working directory must be rejected");
+
+        assert!(error.contains("outside the allowed scope"));
+    }
+}
diff --git a/apps/desktop/src-tauri/src/core/built_in_tools/types.rs b/apps/desktop/src-tauri/src/core/built_in_tools/types.rs
index 8159b1ea..939a5d1f 100644
--- a/apps/desktop/src-tauri/src/core/built_in_tools/types.rs
+++ b/apps/desktop/src-tauri/src/core/built_in_tools/types.rs
@@ -14,6 +14,8 @@ pub struct BuiltInBashExecutionRequest {
     pub command: String,
     /// 可选工作目录。留空时沿用当前进程工作目录。
     pub working_directory: Option<String>,
+    #[serde(default)]
+    pub allowed_working_directories: Vec<String>,
     /// 可选超时，单位毫秒。
     pub timeout_ms: Option<u64>,
     /// 是否启用输出压缩：执行前自动为命令添加压缩前缀以精简输出。
diff --git a/apps/desktop/src/services/BuiltInToolService/tools/bash/helper.ts b/apps/desktop/src/services/BuiltInToolService/tools/bash/helper.ts
index 81cf4e6d..2eb8cb77 100644
--- a/apps/desktop/src/services/BuiltInToolService/tools/bash/helper.ts
+++ b/apps/desktop/src/services/BuiltInToolService/tools/bash/helper.ts
@@ -16,7 +16,49 @@ import {
 } from './constants';
 
 function normalizeDirectoryPath(path: string): string {
-    return path.replace(/\//g, '\\').replace(/\\+$/, '').toLowerCase();
+    const normalizedSeparators = path.trim().replace(/\//g, '\\').replace(/\\+$/, '');
+    const uncMatch = /^\\\\([^\\]+)\\([^\\]+)(?:\\(.*))?$/.exec(normalizedSeparators);
+    const driveMatch = /^([a-zA-Z]:)(?:\\(.*))?$/.exec(normalizedSeparators);
+    const hasRoot = normalizedSeparators.startsWith('\\');
+    const prefix =
+        uncMatch && uncMatch[1] && uncMatch[2]
+            ? `\\\\${uncMatch[1].toLowerCase()}\\${uncMatch[2].toLowerCase()}`
+            : (driveMatch?.[1]?.toLowerCase() ?? (hasRoot ? '\\' : ''));
+    const body = uncMatch
+        ? (uncMatch[3] ?? '')
+        : driveMatch
+          ? (driveMatch[2] ?? '')
+          : normalizedSeparators.replace(/^\\+/, '');
+    const resolvedSegments: string[] = [];
+
+    for (const segment of body.split(/\\+/)) {
+        if (!segment || segment === '.') {
+            continue;
+        }
+
+        if (segment === '..') {
+            const lastSegment = resolvedSegments[resolvedSegments.length - 1];
+            if (lastSegment && lastSegment !== '..') {
+                resolvedSegments.pop();
+            } else if (!prefix) {
+                resolvedSegments.push(segment);
+            }
+            continue;
+        }
+
+        resolvedSegments.push(segment.toLowerCase());
+    }
+
+    const normalizedBody = resolvedSegments.join('\\');
+    if (!prefix) {
+        return normalizedBody;
+    }
+
+    if (!normalizedBody) {
+        return prefix;
+    }
+
+    return prefix.endsWith('\\') ? `${prefix}${normalizedBody}` : `${prefix}\\${normalizedBody}`;
 }
 
 function isWithinAllowedDirectory(path: string, allowlist: string[]): boolean {
diff --git a/apps/desktop/src/services/BuiltInToolService/tools/bash/index.ts b/apps/desktop/src/services/BuiltInToolService/tools/bash/index.ts
index 8eae42d3..7c23291a 100644
--- a/apps/desktop/src/services/BuiltInToolService/tools/bash/index.ts
+++ b/apps/desktop/src/services/BuiltInToolService/tools/bash/index.ts
@@ -52,6 +52,7 @@ async function executeCancelableBash(
         executionId: string;
         command: string;
         workingDirectory?: string | null;
+        allowedWorkingDirectories?: string[];
         timeoutMs?: number | null;
         compactOutput?: boolean;
         rawOutput?: boolean;
@@ -158,6 +159,7 @@ export async function executeBashTool(
             executionId: context.callId,
             command: commandContext.command,
             workingDirectory: commandContext.workingDirectory,
+            allowedWorkingDirectories: config.allowedWorkingDirectories,
             timeoutMs: config.timeoutMs,
             compactOutput: config.compactOutput,
             rawOutput: commandContext.rawOutput,
diff --git a/apps/desktop/src/services/NativeService/types.ts b/apps/desktop/src/services/NativeService/types.ts
index a3a52379..0a4921f8 100644
--- a/apps/desktop/src/services/NativeService/types.ts
+++ b/apps/desktop/src/services/NativeService/types.ts
@@ -15,6 +15,7 @@ export interface BuiltInBashExecutionRequest {
     executionId: string;
     command: string;
     workingDirectory?: string | null;
+    allowedWorkingDirectories?: string[];
     timeoutMs?: number | null;
     compactOutput?: boolean;
     rawOutput?: boolean;
diff --git a/apps/desktop/tests/services/BuiltInToolService/tools/bash/helper.test.ts b/apps/desktop/tests/services/BuiltInToolService/tools/bash/helper.test.ts
index 15741d99..f9b5c29c 100644
--- a/apps/desktop/tests/services/BuiltInToolService/tools/bash/helper.test.ts
+++ b/apps/desktop/tests/services/BuiltInToolService/tools/bash/helper.test.ts
@@ -94,6 +94,48 @@ describe('resolveCommandContext', () => {
         ).rejects.toThrow('Working directory is outside the allowed scope');
     });
 
+    it('rejects working directories that escape the allowlist with parent segments', async () => {
+        setLocale('en-US');
+        const config = {
+            ...baseConfig,
+            allowedWorkingDirectories: ['D:/allowed'],
+        };
+
+        await expect(
+            resolveCommandContext(
+                { command: 'dir', workingDirectory: 'D:/allowed/../other' },
+                config
+            )
+        ).rejects.toThrow('Working directory is outside the allowed scope');
+    });
+
+    it('rejects relative working directories that escape with consecutive parent segments', async () => {
+        setLocale('en-US');
+        const config = {
+            ...baseConfig,
+            allowedWorkingDirectories: ['foo'],
+        };
+
+        await expect(
+            resolveCommandContext({ command: 'dir', workingDirectory: '../../foo' }, config)
+        ).rejects.toThrow('Working directory is outside the allowed scope');
+    });
+
+    it('rejects UNC paths that escape to a sibling share before re-entering the allowlist', async () => {
+        setLocale('en-US');
+        const config = {
+            ...baseConfig,
+            allowedWorkingDirectories: ['\\\\server\\share'],
+        };
+
+        await expect(
+            resolveCommandContext(
+                { command: 'dir', workingDirectory: '\\\\server\\other\\..\\share\\secret' },
+                config
+            )
+        ).rejects.toThrow('Working directory is outside the allowed scope');
+    });
+
     it('accepts command inside allowed directories', async () => {
         const config = {
             ...baseConfig,
diff --git a/apps/desktop/tests/services/BuiltInToolService/tools/bash/index.test.ts b/apps/desktop/tests/services/BuiltInToolService/tools/bash/index.test.ts
index af8b8484..c6024610 100644
--- a/apps/desktop/tests/services/BuiltInToolService/tools/bash/index.test.ts
+++ b/apps/desktop/tests/services/BuiltInToolService/tools/bash/index.test.ts
@@ -128,6 +128,7 @@ describe('executeBashTool request construction', () => {
         const config = {
             ...DEFAULT_BASH_TOOL_CONFIG,
             defaultWorkingDirectory: 'D:/project',
+            allowedWorkingDirectories: ['D:/other'],
             compactOutput: true,
             timeoutMs: 20000,
         };
@@ -143,6 +144,7 @@ describe('executeBashTool request construction', () => {
                 executionId: 'call-1',
                 command: 'git diff',
                 workingDirectory: 'D:/other',
+                allowedWorkingDirectories: ['D:/other'],
                 timeoutMs: 20000,
                 compactOutput: true,
                 rawOutput: true,