diff --git a/pkg/tools/filesystem.go b/pkg/tools/filesystem.go
index d25ec1254..92946ef98 100644
--- a/pkg/tools/filesystem.go
+++ b/pkg/tools/filesystem.go
@@ -82,22 +82,19 @@ func isAllowedPath(path string, patterns []*regexp.Regexp) bool {
 	}
 
 	cleaned := filepath.Clean(path)
+	if !filepath.IsAbs(cleaned) {
+		return false
+	}
 	if !matchesAllowedPath(cleaned, patterns) {
 		return false
 	}
 
-	resolved, err := filepath.EvalSymlinks(cleaned)
-	if err == nil {
-		return matchesAllowedPath(resolved, patterns)
-	}
-	if os.IsNotExist(err) {
-		parentResolved, parentErr := resolveExistingAncestor(filepath.Dir(cleaned))
-		if parentErr == nil {
-			return matchesAllowedPath(parentResolved, patterns)
-		}
+	resolved, err := resolvePathAgainstExistingAncestor(cleaned)
+	if err != nil {
+		return false
 	}
 
-	return false
+	return matchesAllowedPath(resolved, patterns)
 }
 
 func matchesAllowedPath(path string, patterns []*regexp.Regexp) bool {
@@ -122,6 +119,29 @@ func resolveExistingAncestor(path string) (string, error) {
 	}
 }
 
+func resolvePathAgainstExistingAncestor(path string) (string, error) {
+	cleaned := filepath.Clean(path)
+	for current := cleaned; ; current = filepath.Dir(current) {
+		resolved, err := filepath.EvalSymlinks(current)
+		if err == nil {
+			suffix, relErr := filepath.Rel(current, cleaned)
+			if relErr != nil {
+				return "", relErr
+			}
+			if suffix == "." {
+				return filepath.Clean(resolved), nil
+			}
+			return filepath.Clean(filepath.Join(resolved, suffix)), nil
+		}
+		if !os.IsNotExist(err) {
+			return "", err
+		}
+		if filepath.Dir(current) == current {
+			return "", os.ErrNotExist
+		}
+	}
+}
+
 func isWithinWorkspace(candidate, workspace string) bool {
 	rel, err := filepath.Rel(filepath.Clean(workspace), filepath.Clean(candidate))
 	return err == nil && filepath.IsLocal(rel)
@@ -661,7 +681,7 @@ type whitelistFs struct {
 }
 
 func (w *whitelistFs) matches(path string) bool {
-	return matchesAllowedPath(path, w.patterns)
+	return isAllowedPath(path, w.patterns)
 }
 
 func (w *whitelistFs) ReadFile(path string) ([]byte, error) {
diff --git a/pkg/tools/filesystem_test.go b/pkg/tools/filesystem_test.go
index 0bbf6caf0..78d69273f 100644
--- a/pkg/tools/filesystem_test.go
+++ b/pkg/tools/filesystem_test.go
@@ -521,6 +521,55 @@ func TestWhitelistFs_AllowsMatchingPaths(t *testing.T) {
 	}
 }
 
+func TestWhitelistFs_BlocksSymlinkEscapeInAllowedDir(t *testing.T) {
+	workspace := t.TempDir()
+	allowedDir := t.TempDir()
+	secretDir := t.TempDir()
+	secretFile := filepath.Join(secretDir, "secret.txt")
+	if err := os.WriteFile(secretFile, []byte("top secret"), 0o644); err != nil {
+		t.Fatalf("WriteFile(secretFile) error = %v", err)
+	}
+
+	linkPath := filepath.Join(allowedDir, "link_out")
+	if err := os.Symlink(secretDir, linkPath); err != nil {
+		t.Skipf("symlink not supported in this environment: %v", err)
+	}
+
+	patterns := []*regexp.Regexp{regexp.MustCompile(`^` + regexp.QuoteMeta(allowedDir))}
+	tool := NewReadFileTool(workspace, true, MaxReadFileSize, patterns)
+
+	result := tool.Execute(context.Background(), map[string]any{"path": filepath.Join(linkPath, "secret.txt")})
+	if !result.IsError {
+		t.Fatalf("expected symlink escape from allowed dir to be blocked, got: %s", result.ForLLM)
+	}
+}
+
+func TestWhitelistFs_WriteAllowsNewFileUnderAllowedDir(t *testing.T) {
+	workspace := t.TempDir()
+	rootDir := t.TempDir()
+	allowedDir := filepath.Join(rootDir, "allowed")
+	targetFile := filepath.Join(allowedDir, "nested", "file.txt")
+
+	patterns := []*regexp.Regexp{regexp.MustCompile(`^` + regexp.QuoteMeta(allowedDir))}
+	tool := NewWriteFileTool(workspace, true, patterns)
+
+	result := tool.Execute(context.Background(), map[string]any{
+		"path":    targetFile,
+		"content": "outside write",
+	})
+	if result.IsError {
+		t.Fatalf("expected whitelisted write to succeed, got: %s", result.ForLLM)
+	}
+
+	data, err := os.ReadFile(targetFile)
+	if err != nil {
+		t.Fatalf("ReadFile(targetFile) error = %v", err)
+	}
+	if string(data) != "outside write" {
+		t.Fatalf("target file content = %q, want %q", string(data), "outside write")
+	}
+}
+
 // TestReadFileTool_ChunkedReading verifies the pagination logic of the tool
 // by reading a file in multiple chunks using 'offset' and 'length'.
 func TestReadFileTool_ChunkedReading(t *testing.T) {