diff --git a/pkg/tools/shell.go b/pkg/tools/shell.go
index 5f4103dcf..9816dfb30 100644
--- a/pkg/tools/shell.go
+++ b/pkg/tools/shell.go
@@ -95,12 +95,12 @@ var (
 		regexp.MustCompile(`\bssh\b.*@`),
 		regexp.MustCompile(`\beval\b`),
 		regexp.MustCompile(`\bsource\s+.*\.sh\b`),
-		regexp.MustCompile(`\bfind\s+/\b`),       // find / - traverse entire filesystem
-		regexp.MustCompile(`\bls\s+/\b`),         // ls / - list root directory
+		regexp.MustCompile(`\bfind\s+/(\s|[;&|><\n]|$)`), // find / - traverse entire filesystem
+		regexp.MustCompile(`\bls\s+/(\s|[;&|><\n]|$)`),   // ls / - list root directory
 	}
 
 	// absolutePathPattern matches absolute file paths in commands (Unix and Windows).
-	absolutePathPattern = regexp.MustCompile(`[A-Za-z]:\\[^\\\"']+|/(?:[^\s\"']*)?`)
+	absolutePathPattern = regexp.MustCompile(`[A-Za-z]:\\[^\\\"']+|/[^\s\"']*`)
 
 	// safePaths are kernel pseudo-devices that are always safe to reference in
 	// commands, regardless of workspace restriction. They contain no user data
@@ -113,7 +113,7 @@ var (
 		"/dev/stdin":   true,
 		"/dev/stdout":  true,
 		"/dev/stderr":  true,
-		"/":            true,  // root is a path boundary, not a regular file
+		"/":            true, // root is a path boundary, not a regular file
 	}
 )
 
diff --git a/pkg/tools/shell_test.go b/pkg/tools/shell_test.go
index fedc99c45..6a19a6e25 100644
--- a/pkg/tools/shell_test.go
+++ b/pkg/tools/shell_test.go
@@ -1621,12 +1621,38 @@ func TestShellTool_FindRootBlocked(t *testing.T) {
 		t.Fatalf("unable to configure exec tool: %s", err)
 	}
 
+	// Commands that attempt to traverse or list the root filesystem.
+	// Each must be blocked by either a deny-pattern match or the
+	// workspace-boundary check.
 	blocked := []string{
+		// deny pattern: find /
 		"find / -name 'private*' -type f 2>/dev/null",
-		"find /etc -name 'passwd'",
 		"find / -type f -name '*.key'",
+		"find / -maxdepth 1",
+		// deny pattern: ls /
 		"ls /",
+		"ls / -la",
+		// workspace check: find /<path>
+		"find /etc -name 'passwd'",
+		"find /var/log -name '*.log'",
+		// workspace check: ls /<path>
 		"ls /etc",
+		"ls /root",
+		// shell metacharacter bypass attempts
+		"find /;",
+		"find /& ",
+		"find /| cat",
+		"find /&& echo done",
+		"find /|| echo fail",
+		"ls /;",
+		"ls /& ",
+		"ls /| wc -l",
+		"ls /&& echo done",
+		"ls /|| echo fail",
+		// uppercase / mixed case (matching is case-insensitive)
+		"FIND /",
+		"Ls /",
+		"Find / -name passwd",
 	}
 
 	for _, cmd := range blocked {
@@ -1650,10 +1676,19 @@ func TestShellTool_FindInWorkspaceAllowed(t *testing.T) {
 		t.Fatalf("unable to configure exec tool: %s", err)
 	}
 
+	// Legitimate workspace-relative commands that must not be blocked.
 	allowed := []string{
 		"find . -name '*.go'",
 		"find -name '*.txt'",
+		"find workspace -type d",
 		"echo hello",
+		"ls -la",
+		// these match the find/ls prefix but not the root-path pattern
+		"findfile",
+		"lst",
+		// find/ls used on single-component relative paths (no slash)
+		"find sub -name '*.go'",
+		"ls sub",
 	}
 
 	for _, cmd := range allowed {
@@ -1666,3 +1701,54 @@ func TestShellTool_FindInWorkspaceAllowed(t *testing.T) {
 		}
 	}
 }
+
+func TestShellTool_FindRootBlocked_DenyDisabled(t *testing.T) {
+	// When deny patterns are disabled, find / and ls / should still be
+	// caught by the workspace-boundary check (since / is outside the
+	// workspace).
+	tmpDir := t.TempDir()
+	cfg := &config.Config{}
+	cfg.Tools.Exec.EnableDenyPatterns = false
+
+	tool, err := NewExecToolWithConfig(tmpDir, true, cfg)
+	if err != nil {
+		t.Fatalf("unable to configure exec tool: %s", err)
+	}
+
+	// These are blocked by workspace restriction even without deny patterns.
+	blocked := []string{
+		"find /etc -name passwd",
+		"ls /etc",
+		"find /;",
+		"ls /;",
+	}
+
+	for _, cmd := range blocked {
+		result := tool.Execute(context.Background(), map[string]any{
+			"action":  "run",
+			"command": cmd,
+		})
+		if !result.IsError {
+			t.Errorf("expected command to be blocked (workspace check): %s", cmd)
+		}
+	}
+
+	// find / and ls / with bare root *can* execute when deny patterns
+	// are disabled because / is in safePaths.
+	bareRoot := []string{
+		"find / -maxdepth 1",
+		"ls /",
+	}
+	for _, cmd := range bareRoot {
+		result := tool.Execute(context.Background(), map[string]any{
+			"action":  "run",
+			"command": cmd,
+		})
+		if result.IsError && strings.Contains(result.ForLLM, "blocked") {
+			t.Errorf(
+				"bare root command should not be workspace-blocked (safePaths): %s\n  error: %s",
+				cmd, result.ForLLM,
+			)
+		}
+	}
+}