If Mail Fails to Send, Try, Try Again (Instead of Changing Servers)

Sometimes, something goes wrong, causing Mail on the Mac to have trouble sending a message. When it does, you may see an error like the one below, encouraging you with a default button to try another configured server. Don’t do it! Always click Try Later. If that still doesn’t work, contact your favorite tech support professional to troubleshoot the problem with the SMTP server associated with the account from which you’re sending. Attempting to send through another SMTP server is a recipe for trouble because various anti-spam checks may fail, causing your message to be filtered as spam or bounced back to you. Worse, if you select a different server and click Try With Selected Server, Mail remembers that choice going forward, so you will have to reset it manually later.

(Featured image by iStock.com/Marut Khobtakhob)