diff --git a/ms_agent/permission/shell_validator.py b/ms_agent/permission/shell_validator.py
index 506a8d073..e0e23e10f 100644
--- a/ms_agent/permission/shell_validator.py
+++ b/ms_agent/permission/shell_validator.py
@@ -126,8 +126,12 @@ def check(self, command: str, *, _depth: int = 0) -> SafetyDecision:
             if not tokens:
                 continue
 
-            # 3. Check output redirections on the raw sub-command string
-            redirect_result = self._check_redirects(sub_cmd)
+            # 3. Check output redirections on the raw sub-command string.
+            # Resolve relative targets against the cd-tracked cwd, matching
+            # how the shell itself resolves them. Note this runs before the
+            # `cd` below updates _current_cwd, which is also what the shell
+            # does for a command like `cd foo > log`.
+            redirect_result = self._check_redirects(sub_cmd, cwd=_current_cwd)
             if redirect_result.action != 'allow':
                 return redirect_result
 
@@ -325,7 +329,11 @@ def _validate_paths(
         return SafetyDecision(
             action='allow', reason=f'{cmd_name}: all paths validated')
 
-    def _check_redirects(self, sub_cmd: str) -> SafetyDecision:
+    def _check_redirects(self,
+                         sub_cmd: str,
+                         *,
+                         cwd: str | None = None) -> SafetyDecision:
+        effective_cwd = cwd or self._workspace_root
         for match in _REDIRECT_PATTERN.finditer(sub_cmd):
             target = match.group(1)
             if _FD_REDIRECT.match(target):
@@ -341,7 +349,7 @@ def _check_redirects(self, sub_cmd: str) -> SafetyDecision:
 
             result = validate_path(
                 target,
-                self._workspace_root,
+                effective_cwd,
                 self._allowed_dirs,
                 'create',
                 read_only_dirs=self._read_only_dirs,
diff --git a/tests/permission/test_shell_validator.py b/tests/permission/test_shell_validator.py
index 2f214b3ab..97151740b 100644
--- a/tests/permission/test_shell_validator.py
+++ b/tests/permission/test_shell_validator.py
@@ -5,7 +5,8 @@
 
 import pytest
 
-from ms_agent.permission.shell_validator import ShellPathValidator
+from ms_agent.permission.shell_validator import (PathSafetyConfig,
+                                                 ShellPathValidator)
 
 
 @pytest.fixture
@@ -99,6 +100,60 @@ def test_redirect_with_variable(self, validator):
         assert r.action == 'deny'
 
 
+class TestRedirectCwdTracking:
+    """Relative redirect targets must resolve against the cd-tracked cwd.
+
+    The shell resolves ``>`` targets against the current working directory,
+    so a compound command like ``cd sub && echo x > ../f`` writes to
+    ``<cwd>/sub/../f``. Validating the target against the workspace root
+    instead disagrees with what actually happens on disk in both directions.
+    """
+
+    @pytest.fixture
+    def layout(self, tmp_path):
+        work = tmp_path / 'a' / 'b' / 'work'
+        work2 = tmp_path / 'a' / 'b' / 'work2'
+        cache = tmp_path / 'cache'
+        for p in (work / 'sub', work2, cache):
+            p.mkdir(parents=True)
+        allowed = (str(work), str(work2), str(cache))
+        validator = ShellPathValidator(
+            allowed_dirs=list(allowed),
+            safety_config=PathSafetyConfig(
+                allowed_directories=allowed, workspace_root=str(work)),
+        )
+        return validator, work, work2, cache
+
+    def test_relative_redirect_after_cd_into_subdir(self, layout):
+        """``cd work/sub && echo x > ../f`` writes work/f — inside allowed."""
+        validator, work, _, _ = layout
+        r = validator.check(f'cd {work}/sub && echo x > ../f')
+        assert r.action == 'allow'
+
+    def test_relative_redirect_escaping_after_cd(self, layout):
+        """``cd cache && echo x > ../work2/f`` writes outside allowed dirs.
+
+        Resolved against the workspace root the target would look like
+        ``work/../work2/f`` (an allowed directory), but the shell writes to
+        ``cache/../work2/f``, which is not allowed.
+        """
+        validator, _, _, cache = layout
+        r = validator.check(f'cd {cache} && echo x > ../work2/f')
+        assert r.action != 'allow'
+
+    def test_redirect_without_cd_uses_workspace_root(self, layout):
+        validator, _, _, _ = layout
+        r = validator.check('echo x > f')
+        assert r.action == 'allow'
+
+    def test_redirect_matches_argument_path_validation(self, layout):
+        """Redirects and ordinary path arguments must agree on the cwd."""
+        validator, work, _, _ = layout
+        rm = validator.check(f'cd {work}/sub && rm ../f')
+        redirect = validator.check(f'cd {work}/sub && echo x > ../f')
+        assert rm.action == redirect.action == 'allow'
+
+
 class TestProcessSubstitution:
     def test_output_substitution(self, validator):
         r = validator.check('echo secret > >(tee .git/config)')