diff --git a/pkg/tools/shell.go b/pkg/tools/shell.go
index d9430672f..f23504139 100644
--- a/pkg/tools/shell.go
+++ b/pkg/tools/shell.go
@@ -143,6 +143,29 @@ func (t *ExecTool) Execute(ctx context.Context, args map[string]interface{}) *To
 
 	cwd := t.workingDir
 	if wd, ok := args["working_dir"].(string); ok && wd != "" {
+		if t.restrictToWorkspace && t.workingDir != "" {
+			absWD, err := filepath.Abs(wd)
+			if err != nil {
+				return ErrorResult("invalid working_dir path")
+			}
+			absWorkspace, err := filepath.Abs(t.workingDir)
+			if err != nil {
+				return ErrorResult("failed to resolve workspace path")
+			}
+			if !isWithinWorkspace(absWD, absWorkspace) {
+				return ErrorResult("Command blocked by safety guard (working_dir outside workspace)")
+			}
+			// Also check symlink resolution
+			if resolved, err := filepath.EvalSymlinks(absWD); err == nil {
+				workspaceReal := absWorkspace
+				if r, err := filepath.EvalSymlinks(absWorkspace); err == nil {
+					workspaceReal = r
+				}
+				if !isWithinWorkspace(resolved, workspaceReal) {
+					return ErrorResult("Command blocked by safety guard (working_dir symlink resolves outside workspace)")
+				}
+			}
+		}
 		cwd = wd
 	}