diff --git a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/systemOneUI/lib/curlCommand.test.ts b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/systemOneUI/lib/curlCommand.test.ts
index 9404e703ca6..4cd749ba913 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/systemOneUI/lib/curlCommand.test.ts
+++ b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/systemOneUI/lib/curlCommand.test.ts
@@ -1,3 +1,4 @@
+import { execFileSync } from "node:child_process";
 import { describe, expect, it } from "vitest";
 import { buildCurlCommand, curlPayload } from "./curlCommand";
 
@@ -12,7 +13,7 @@ describe("buildCurlCommand", () => {
     const command = buildCurlCommand(input);
 
     expect(command).toContain("curl -X POST 'http://localhost:4000/v1/systemone'");
-    expect(command).toContain("-H 'Authorization: Bearer $LITELLM_API_KEY'");
+    expect(command).toContain('-H "Authorization: Bearer $LITELLM_API_KEY"');
     expect(command).not.toContain("sk-");
     expect(command).toContain('  "state": "it\'\\\'\'s broken"');
     expect(JSON.parse(curlPayload(command) ?? "")).toEqual({ model: "jev-latest", state: "it's broken" });
@@ -37,10 +38,26 @@ describe("buildCurlCommand", () => {
       authHeaderName: "X-Litellm-Key",
     };
     const command = buildCurlCommand(input);
-    expect(command).toContain("-H 'X-Litellm-Key: Bearer $LITELLM_API_KEY'");
+    expect(command).toContain('-H "X-Litellm-Key: Bearer $LITELLM_API_KEY"');
     expect(command).not.toContain("Authorization");
   });
 
+  it("lets the shell expand the key while a hostile header name stays literal", () => {
+    const input = {
+      baseUrl: "https://proxy.example",
+      endpoint: "/v1/systemone" as const,
+      payload: "{}",
+      authHeaderName: 'X-"$(touch pwned)`id`\\Key',
+    };
+    const command = buildCurlCommand(input);
+    const args = execFileSync("bash", ["-c", command.replace(/^curl /, "printf '%s\\n' ")], {
+      encoding: "utf8",
+      env: { ...process.env, LITELLM_API_KEY: "sk-test-key" },
+    });
+    expect(args).toContain('X-"$(touch pwned)`id`\\Key: Bearer sk-test-key\n');
+    expect(args).not.toContain("$LITELLM_API_KEY");
+  });
+
   it("passes a payload that is not JSON through untouched", () => {
     const input = {
       baseUrl: "https://proxy.example",
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/systemOneUI/lib/curlCommand.ts b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/systemOneUI/lib/curlCommand.ts
index 1153107cade..27d44bb0b04 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/systemOneUI/lib/curlCommand.ts
+++ b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/systemOneUI/lib/curlCommand.ts
@@ -9,6 +9,8 @@ export const CURL_KEY_PLACEHOLDER = "$LITELLM_API_KEY";
 
 const shellSingleQuote = (value: string): string => `'${value.replace(/'/g, `'\\''`)}'`;
 
+const shellDoubleQuoteLiteral = (value: string): string => value.replace(/["\\$`]/g, (char) => `\\${char}`);
+
 const prettyPayload = (payload: string): string => {
   try {
     return JSON.stringify(JSON.parse(payload), null, 2);
@@ -20,7 +22,7 @@ const prettyPayload = (payload: string): string => {
 export const buildCurlCommand = ({ baseUrl, endpoint, payload, authHeaderName }: CurlCommandInput): string =>
   [
     `curl -X POST ${shellSingleQuote(`${baseUrl.replace(/\/+$/, "")}${endpoint}`)}`,
-    `  -H ${shellSingleQuote(`${authHeaderName}: Bearer ${CURL_KEY_PLACEHOLDER}`)}`,
+    `  -H "${shellDoubleQuoteLiteral(authHeaderName)}: Bearer ${CURL_KEY_PLACEHOLDER}"`,
     `  -H "Content-Type: application/json"`,
     `  -d ${shellSingleQuote(prettyPayload(payload))}`,
   ].join(" \\\n");