diff --git a/.changeset/ninety-comics-scream.md b/.changeset/ninety-comics-scream.md
new file mode 100644
index 0000000000..e0b493c282
--- /dev/null
+++ b/.changeset/ninety-comics-scream.md
@@ -0,0 +1,5 @@
+---
+"@clerk/backend": patch
+---
+
+Improve debugging error reasons.
diff --git a/packages/backend/src/errors.ts b/packages/backend/src/errors.ts
index 111cf4d8ec..90cfdc343a 100644
--- a/packages/backend/src/errors.ts
+++ b/packages/backend/src/errors.ts
@@ -13,6 +13,7 @@ export const TokenVerificationErrorReason = {
   TokenInvalidAuthorizedParties: 'token-invalid-authorized-parties',
   TokenInvalidSignature: 'token-invalid-signature',
   TokenNotActiveYet: 'token-not-active-yet',
+  TokenIatInTheFuture: 'token-iat-in-the-future',
   TokenVerificationFailed: 'token-verification-failed',
   InvalidSecretKey: 'secret-key-invalid',
   LocalJWKMissing: 'jwk-local-missing',
diff --git a/packages/backend/src/jwt/assertions.ts b/packages/backend/src/jwt/assertions.ts
index f91e9b2636..4153de625f 100644
--- a/packages/backend/src/jwt/assertions.ts
+++ b/packages/backend/src/jwt/assertions.ts
@@ -162,7 +162,7 @@ export const assertIssuedAtClaim = (iat: number | undefined, clockSkewInMs: numb
   const postIssued = issuedAtDate.getTime() > currentDate.getTime() + clockSkewInMs;
   if (postIssued) {
     throw new TokenVerificationError({
-      reason: TokenVerificationErrorReason.TokenNotActiveYet,
+      reason: TokenVerificationErrorReason.TokenIatInTheFuture,
       message: `JWT issued at date claim (iat) is in the future. Issued at date: ${issuedAtDate.toUTCString()}; Current date: ${currentDate.toUTCString()};`,
     });
   }
diff --git a/packages/backend/src/tokens/__tests__/request.test.ts b/packages/backend/src/tokens/__tests__/request.test.ts
index 73a68c74ba..e72c8904b1 100644
--- a/packages/backend/src/tokens/__tests__/request.test.ts
+++ b/packages/backend/src/tokens/__tests__/request.test.ts
@@ -238,7 +238,7 @@ export default (QUnit: QUnit) => {
 
       const requestState = await authenticateRequest(mockRequestWithHeaderAuth(), mockOptions());
 
-      assertHandshake(assert, requestState, { reason: AuthErrorReason.SessionTokenOutdated });
+      assertHandshake(assert, requestState, { reason: AuthErrorReason.SessionTokenExpired });
       assert.strictEqual(requestState.toAuth(), null);
     });
 
@@ -487,7 +487,7 @@ export default (QUnit: QUnit) => {
         mockOptions(),
       );
 
-      assertHandshake(assert, requestState, { reason: AuthErrorReason.SessionTokenOutdated });
+      assertHandshake(assert, requestState, { reason: AuthErrorReason.SessionTokenIATBeforeClientUAT });
       assert.equal(requestState.message, '');
       assert.strictEqual(requestState.toAuth(), null);
     });
@@ -554,7 +554,7 @@ export default (QUnit: QUnit) => {
         mockOptions(),
       );
 
-      assertHandshake(assert, requestState, { reason: AuthErrorReason.SessionTokenOutdated });
+      assertHandshake(assert, requestState, { reason: AuthErrorReason.SessionTokenExpired });
       assert.true(/^JWT is expired/.test(requestState.message || ''));
       assert.strictEqual(requestState.toAuth(), null);
     });
diff --git a/packages/backend/src/tokens/authStatus.ts b/packages/backend/src/tokens/authStatus.ts
index 78a7de9c12..ec836e6a85 100644
--- a/packages/backend/src/tokens/authStatus.ts
+++ b/packages/backend/src/tokens/authStatus.ts
@@ -64,7 +64,10 @@ export const AuthErrorReason = {
   SatelliteCookieNeedsSyncing: 'satellite-needs-syncing',
   SessionTokenAndUATMissing: 'session-token-and-uat-missing',
   SessionTokenMissing: 'session-token-missing',
-  SessionTokenOutdated: 'session-token-outdated',
+  SessionTokenExpired: 'session-token-expired',
+  SessionTokenIATBeforeClientUAT: 'session-token-iat-before-client-uat',
+  SessionTokenNotActiveYet: 'session-token-not-active-yet',
+  SessionTokenIatInTheFuture: 'session-token-iat-in-the-future',
   SessionTokenWithoutClientUAT: 'session-token-but-no-client-uat',
   UnexpectedError: 'unexpected-error',
 } as const;
diff --git a/packages/backend/src/tokens/request.ts b/packages/backend/src/tokens/request.ts
index 53c5c19f2d..9a3bb1257f 100644
--- a/packages/backend/src/tokens/request.ts
+++ b/packages/backend/src/tokens/request.ts
@@ -165,7 +165,8 @@ export async function authenticateRequest(
     if (
       authenticateContext.instanceType === 'development' &&
       (error?.reason === TokenVerificationErrorReason.TokenExpired ||
-        error?.reason === TokenVerificationErrorReason.TokenNotActiveYet)
+        error?.reason === TokenVerificationErrorReason.TokenNotActiveYet ||
+        error?.reason === TokenVerificationErrorReason.TokenIatInTheFuture)
     ) {
       error.tokenCarrier = 'cookie';
       // This probably means we're dealing with clock skew
@@ -456,7 +457,7 @@ ${error.getFullMessage()}`,
     }
 
     if (decodeResult.payload.iat < authenticateContext.clientUat) {
-      return handleMaybeHandshakeStatus(authenticateContext, AuthErrorReason.SessionTokenOutdated, '');
+      return handleMaybeHandshakeStatus(authenticateContext, AuthErrorReason.SessionTokenIATBeforeClientUAT, '');
     }
 
     try {
@@ -502,12 +503,13 @@ ${error.getFullMessage()}`,
     const reasonToHandshake = [
       TokenVerificationErrorReason.TokenExpired,
       TokenVerificationErrorReason.TokenNotActiveYet,
+      TokenVerificationErrorReason.TokenIatInTheFuture,
     ].includes(err.reason);
 
     if (reasonToHandshake) {
       return handleMaybeHandshakeStatus(
         authenticateContext,
-        AuthErrorReason.SessionTokenOutdated,
+        convertTokenVerificationErrorReasonToAuthErrorReason(err.reason),
         err.getFullMessage(),
         undefined,
         refreshError,
@@ -531,3 +533,18 @@ export const debugRequestState = (params: RequestState) => {
   const { isSignedIn, proxyUrl, reason, message, publishableKey, isSatellite, domain } = params;
   return { isSignedIn, proxyUrl, reason, message, publishableKey, isSatellite, domain };
 };
+
+const convertTokenVerificationErrorReasonToAuthErrorReason = (
+  reason: TokenVerificationErrorReason,
+): AuthErrorReason => {
+  switch (reason) {
+    case TokenVerificationErrorReason.TokenExpired:
+      return AuthErrorReason.SessionTokenExpired;
+    case TokenVerificationErrorReason.TokenNotActiveYet:
+      return AuthErrorReason.SessionTokenNotActiveYet;
+    case TokenVerificationErrorReason.TokenIatInTheFuture:
+      return AuthErrorReason.SessionTokenIatInTheFuture;
+    default:
+      return AuthErrorReason.UnexpectedError;
+  }
+};