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)


Social Media: If Mail on your Mac throws an error about being unable to send a message, always have it try again later rather than switching to a different server. Otherwise, your messages may look like spam and be blocked.

More Insights

Tech Article

Stay Safe in 2026 with These New Year’s Resolutions

We’re approaching the end of 2025, so we encourage you to consider your New Year’s resolutions. For many people, the new year offers an opportunity to reflect on habits we’d like to adopt or solidify. Although we support reducing social media use and making other positive lifestyle changes, we’d like to suggest a few additional […]

Read More »
Tech Tip

Create Reminders to Return Calls Directly in the Phone App

Apple introduced a neat new feature in the Phone app in iOS 26 and iPadOS 26 (but not macOS 26): callback reminders. Whenever you miss a call and think, “I’d better call this person back later,” you can now create a reminder to do that right within the Phone app. Swipe left on any call, […]

Read More »
Tech Tip

Clean Up Your Mac’s Login Items for Better Performance

If you use certain apps or documents regularly, you can ensure they’re ready to go after a restart by manually adding them to your Login Items list. Some login items are also added automatically by apps that want to be available at all times. Either way, when the Mac boots, it automatically opens all login […]

Read More »
Tech Article

Spotlight Gets Brighter in macOS 26 Tahoe

Spotlight has been a staple on macOS for decades, and at various points in its history, Apple has added new search capabilities. However, the revamp that Spotlight enjoyed in macOS 26 Tahoe is the most significant change in a long time. Here are the new features you’ll experience in Tahoe. Filterable Interface Apple has refocused […]

Read More »
Tech Tip

Messages Now Offers Shared Conversation Backgrounds

A potentially surprising and fun new feature in Messages in iOS 26, iPadOS 26, and macOS 26 Tahoe is conversation backgrounds. To set one, tap the person or group icon at the top of the conversation, then tap Backgrounds, select an image, and tap the blue checkmark to save. What you might not realize is […]

Read More »
Tech Article

Automate Your Mac with Folder Action Scripts

Do you repeatedly find yourself wanting to do something in the Finder with every file of a certain type? Perhaps you regularly download files from a particular website that come in with a .txt extension, even though they’re CSV files that should have a .csv extension? Or maybe you want to rename files according to […]

Read More »

If you are here and not sure how to proceed, please call us at 626-286-2350, and we would be happy to help you find a solution to your needs.