diff --git a/src/actions/auth/status.ts b/src/actions/auth/status.ts
index e77432bd..fc042abe 100644
--- a/src/actions/auth/status.ts
+++ b/src/actions/auth/status.ts
@@ -13,7 +13,11 @@ export class StatusAction {
 
   public async execute(authKey: string | null): Promise<ActionResult> {
     const accountInfo = await getAuthInfo(this.configDir.toString());
-    if (accountInfo === null) {
+    // `auth logout` blanks config.json rather than deleting it, so a logged-out user still
+    // has a non-null AuthInfo with an empty key. Checking the key catches both that and a
+    // missing config file, and avoids a request that can only come back 401.
+    if (!accountInfo?.authKey) {
+      this.prompts.notLoggedIn();
       return ActionResult.failed();
     }
     const result = await this.prompts.accountInfoSpinner(
diff --git a/src/infrastructure/services/publishing-api-service.ts b/src/infrastructure/services/publishing-api-service.ts
index e207c638..f03f0b55 100644
--- a/src/infrastructure/services/publishing-api-service.ts
+++ b/src/infrastructure/services/publishing-api-service.ts
@@ -24,8 +24,10 @@ export class PublishingApiService {
     shell: string
   ): Promise<Result<PublishingProfileItem[], ServiceError>> {
     const authInfo: AuthInfo | null = await getAuthInfo(configDir.toString());
-    if (authInfo === null) {
-      return err(ServiceError.UnAuthorized);
+    // `auth logout` blanks config.json rather than deleting it, so a logged-out user
+    // still has a non-null AuthInfo with an empty key — check the key, not the object.
+    if (!authInfo?.authKey) {
+      return err(ServiceError.unauthorizedWithHint(null));
     }
 
     try {
@@ -51,8 +53,10 @@ export class PublishingApiService {
     shell: string
   ): Promise<Result<PublishingInfo, ServiceError>> {
     const authInfo: AuthInfo | null = await getAuthInfo(configDir.toString());
-    if (authInfo === null) {
-      return err(ServiceError.UnAuthorized);
+    // `auth logout` blanks config.json rather than deleting it, so a logged-out user
+    // still has a non-null AuthInfo with an empty key — check the key, not the object.
+    if (!authInfo?.authKey) {
+      return err(ServiceError.unauthorizedWithHint(null));
     }
     const sdkFileStream = await this.fileService.getStream(sdkFilePath);
 
@@ -107,8 +111,10 @@ export class PublishingApiService {
     shell: string
   ): Promise<Result<PublishLogItem, ServiceError>> {
     const authInfo: AuthInfo | null = await getAuthInfo(configDir.toString());
-    if (authInfo === null) {
-      return err(ServiceError.UnAuthorized);
+    // `auth logout` blanks config.json rather than deleting it, so a logged-out user
+    // still has a non-null AuthInfo with an empty key — check the key, not the object.
+    if (!authInfo?.authKey) {
+      return err(ServiceError.unauthorizedWithHint(null));
     }
 
     try {
diff --git a/src/infrastructure/services/transformation-service.ts b/src/infrastructure/services/transformation-service.ts
index 677aa186..119d4268 100644
--- a/src/infrastructure/services/transformation-service.ts
+++ b/src/infrastructure/services/transformation-service.ts
@@ -17,6 +17,7 @@ import { apiClientFactory } from "./api-client-factory.js";
 import { FilePath } from "../../types/file/filePath.js";
 import { CommandMetadata } from "../../types/common/command-metadata.js";
 import { err, ok, Result} from "neverthrow";
+import { ServiceError } from "../service-error.js";
 
 export interface TransformViaFileParams {
   file: FilePath;
@@ -86,7 +87,7 @@ export class TransformationService {
         return "Your API Definition is invalid. Please use the APIMatic VS Code Extension to fix the errors and try again.";
       } else if (apiError.statusCode === 401) {
         const message = JSON.parse(apiError.body as string).message;
-        return `${message} You are not authorized to perform this action. Please run 'auth:login' or provide a valid auth key.`;
+        return ServiceError.unauthorizedWithHint(message).errorMessage;
       }
       return `Error ${apiError.statusCode}: An error occurred during the transformation. Please try again or contact support@apimatic.io for assistance.`;
     } else {
diff --git a/src/infrastructure/services/validation-service.ts b/src/infrastructure/services/validation-service.ts
index 8a20d753..462af9dd 100644
--- a/src/infrastructure/services/validation-service.ts
+++ b/src/infrastructure/services/validation-service.ts
@@ -247,7 +247,7 @@ export class ValidationService {
         case 400:
           return "Your API Definition is invalid. Please fix the issues and try again.";
         case 401:
-          return "You are not authorized to perform this action. Please run 'auth:login' or provide a valid auth key.";
+          return ServiceError.unauthorizedWithHint(null).errorMessage;
         case 403:
           return "You do not have permission to perform this action.";
         case 500:
diff --git a/src/prompts/auth/status.ts b/src/prompts/auth/status.ts
index 32fc48e6..5b3f9786 100644
--- a/src/prompts/auth/status.ts
+++ b/src/prompts/auth/status.ts
@@ -16,12 +16,17 @@ export class StatusPrompts {
     );
   }
 
+  public notLoggedIn() {
+    log.error(`You are not logged in. Please run ${format.cmdAlt("apimatic", "auth", "login")} to log in.`);
+  }
+
   public invalidKeyProvided(serviceError: ServiceError) {
     const message =
       serviceError === ServiceError.UnAuthorized ? "Invalid API key provided." : serviceError.errorMessage;
     log.error(message);
   }
 
+
   public showAccountInfo(info: SubscriptionInfo) {
     const languages = mapLanguages(info.allowedLanguages);
     const message = `Account Information: