diff --git a/docs/pages/setup/manual.mdx b/docs/pages/setup/manual.mdx
index 58e4251..840eef5 100644
--- a/docs/pages/setup/manual.mdx
+++ b/docs/pages/setup/manual.mdx
@@ -61,7 +61,8 @@ const keys = await generateKeyPair("RS256", {
 });
 const privateKey = await exportPKCS8(keys.privateKey);
 const publicKey = await exportJWK(keys.publicKey);
-const jwks = JSON.stringify({ keys: [{ use: "sig", ...publicKey }] });
+const kid = crypto.randomUUID();
+const jwks = JSON.stringify({ keys: [{ use: "sig", kid, ...publicKey }] });
 
 process.stdout.write(
   `JWT_PRIVATE_KEY="${privateKey.trimEnd().replace(/\n/g, " ")}"`,
@@ -127,5 +128,5 @@ export default http;
 
 </Steps>
 
-Continue to [Step 3](/setup#add-authentication-tables-to-your-schema) in
-the Setup guide.
+Continue to [Step 3](/setup#add-authentication-tables-to-your-schema) in the
+Setup guide.
diff --git a/src/cli/generateKeys.ts b/src/cli/generateKeys.ts
index bad4358..559a6a7 100644
--- a/src/cli/generateKeys.ts
+++ b/src/cli/generateKeys.ts
@@ -5,7 +5,8 @@ export async function generateKeys() {
     const keys = await generateKeyPair("RS256");
     const privateKey = await exportPKCS8(keys.privateKey);
     const publicKey = await exportJWK(keys.publicKey);
-    const jwks = JSON.stringify({ keys: [{ use: "sig", ...publicKey }] });
+    const kid = crypto.randomUUID();
+    const jwks = JSON.stringify({ keys: [{ use: "sig", kid, ...publicKey }] });
     return {
       JWT_PRIVATE_KEY: `${privateKey.trimEnd().replace(/\n/g, " ")}`,
       JWKS: jwks,
diff --git a/src/server/implementation/tokens.ts b/src/server/implementation/tokens.ts
index 3701f24..847f3d0 100644
--- a/src/server/implementation/tokens.ts
+++ b/src/server/implementation/tokens.ts
@@ -1,6 +1,6 @@
 import { GenericId } from "convex/values";
 import { ConvexAuthConfig } from "../index.js";
-import { SignJWT, importPKCS8 } from "jose";
+import { SignJWT, importPKCS8, type JWK } from "jose";
 import { requireEnv } from "../utils.js";
 import { TOKEN_SUB_CLAIM_DIVIDER } from "./utils.js";
 
@@ -17,13 +17,29 @@ export async function generateToken(
   const expirationTime = new Date(
     Date.now() + (config.jwt?.durationMs ?? DEFAULT_JWT_DURATION_MS),
   );
+  const latestJwk = getLatestJwk();
   return await new SignJWT({
     sub: args.userId + TOKEN_SUB_CLAIM_DIVIDER + args.sessionId,
   })
-    .setProtectedHeader({ alg: "RS256" })
+    .setProtectedHeader({ alg: "RS256", kid: latestJwk.kid, typ: "JWT" })
     .setIssuedAt()
     .setIssuer(requireEnv("CONVEX_SITE_URL"))
     .setAudience("convex")
     .setExpirationTime(expirationTime)
     .sign(privateKey);
 }
+
+function getLatestJwk() {
+  try {
+    const jwksString = requireEnv("JWKS");
+    const jwks = JSON.parse(jwksString);
+    // assume the latest JWK is the first one
+    const latestJwk = jwks["keys"][0];
+    if (!latestJwk) {
+      throw new Error("No JWK found");
+    }
+    return latestJwk as JWK;
+  } catch (error) {
+    throw new Error("Error getting latest JWK", { cause: error });
+  }
+}