diff --git a/packages/terminal-security/src/evaluateTerminalCommandSecurity.ts b/packages/terminal-security/src/evaluateTerminalCommandSecurity.ts
index 693eef25f9c..060c1d75a5a 100644
--- a/packages/terminal-security/src/evaluateTerminalCommandSecurity.ts
+++ b/packages/terminal-security/src/evaluateTerminalCommandSecurity.ts
@@ -465,9 +465,12 @@ function isCriticalCommand(baseCommand: string, args: string[]): boolean {
 
   // Windows destructive commands
   if (baseCommand === "del") {
-    const hasRecursive = args.includes("/s") && args.includes("/q");
-    const hasSystemDrive = args.some(
-      (arg) => arg.toLowerCase().includes("c:\\") || arg.includes("c:/"),
+    // Windows switches and drive letters are case-insensitive, so `/S /Q C:\`
+    // has to be treated exactly like `/s /q c:\`
+    const lowerArgs = args.map((arg) => arg.toLowerCase());
+    const hasRecursive = lowerArgs.includes("/s") && lowerArgs.includes("/q");
+    const hasSystemDrive = lowerArgs.some(
+      (arg) => arg.includes("c:\\") || arg.includes("c:/"),
     );
     if (hasRecursive || hasSystemDrive) {
       return true;
diff --git a/packages/terminal-security/test/terminalCommandSecurity.test.ts b/packages/terminal-security/test/terminalCommandSecurity.test.ts
index 7d2e484765e..22663dea9ae 100644
--- a/packages/terminal-security/test/terminalCommandSecurity.test.ts
+++ b/packages/terminal-security/test/terminalCommandSecurity.test.ts
@@ -60,6 +60,22 @@ describe("evaluateTerminalCommandSecurity", () => {
         expect(result).toBe("disabled");
       });
 
+      it("should disable Windows del with uppercase recursive flags", () => {
+        const result = evaluateTerminalCommandSecurity(
+          "allowedWithoutPermission",
+          "DEL /S /Q C:\\",
+        );
+        expect(result).toBe("disabled");
+      });
+
+      it("should disable Windows del on the system drive regardless of case", () => {
+        const result = evaluateTerminalCommandSecurity(
+          "allowedWithoutPermission",
+          "del /Q C:/Windows",
+        );
+        expect(result).toBe("disabled");
+      });
+
       it("should disable dd commands that could overwrite disk", () => {
         const result = evaluateTerminalCommandSecurity(
           "allowedWithoutPermission",