diff --git a/.changeset/few-bats-remember.md b/.changeset/few-bats-remember.md
new file mode 100644
index 000000000..b923f2d9e
--- /dev/null
+++ b/.changeset/few-bats-remember.md
@@ -0,0 +1,5 @@
+---
+'@faustwp/cli': patch
+---
+
+Previously, WordPress connection failures lacked clear feedback. This update adds a proper error message when a 500 error occurs, improving debugging and usability.
diff --git a/packages/faustwp-cli/src/healthCheck/validateNextWordPressUrl.ts b/packages/faustwp-cli/src/healthCheck/validateNextWordPressUrl.ts
index 71d438829..9f79ff29c 100644
--- a/packages/faustwp-cli/src/healthCheck/validateNextWordPressUrl.ts
+++ b/packages/faustwp-cli/src/healthCheck/validateNextWordPressUrl.ts
@@ -28,6 +28,11 @@ export async function validateNextWordPressUrl(): Promise<void> {
 				warnLog(
 					'Route not found: Please update your FaustWP plugin to the latest version.',
 				);
+			} else if (response.status >= 500 && response.status < 600) {
+				// Handle WordPress server error
+				errorLog(
+					'Could not connect to the WordPress server. Please check your WordPress URL or server status, as your site may not function correctly.',
+				);
 			} else {
 				errorLog(
 					'Validation Failed: Your Faust front-end site URL value is misconfigured. It should NOT match the `NEXT_PUBLIC_WORDPRESS_URL.`',