Fix Mac Mail Problems With These Troubleshooting Guides

Use Mail's own built-in troubleshooting tools

Troubleshooting Apple Mail can at first seem like a difficult process, but Apple provides some built-in troubleshooting tools that can help you get your Mail application up and running quickly.

While the troubleshooting tools can take care of many of the Mail issues you may run into, there are other Mail-related problems that the built-in troubleshooting tools won't be able to diagnose. That's why when you're having trouble with Apple Mail, you should check out our Apple Mail Troubleshooting guides, which cover both the problems that are easy to fix and the ones that may need a bit more effort.

Using Apple Mail's Troubleshooting Tools

Apple Mail is very straightforward to set up and use. Apple provides convenient guides that step you through the process for creating accounts. Apple also provides a few troubleshooting guides designed to help you when something isn't working.

The three main assistants for diagnosing problems are the Activity window, the Connection Doctor, and Mail logs. Learning how to use each of these troubleshooting aids can help you quickly resolve Mail issues.

Troubleshooting Apple Mail and a Dimmed Send Button

You've just dashed off a reply to an important email message. When you hit the 'Send' button, you discover that it's dimmed, which means you can't send your message. Mail was working fine yesterday; what went wrong?

This guide will show you the problems that can cause Mail's Send button to be unavailable, and then help you fix the issues, so you can get back to sending that important email.

Transfer Your Apple Mail to a New Mac

Transferring your Apple Mail to another Mac may not seem like much of a troubleshooting-related issue, but the process includes steps to repair your Mac's keychain, which can fix forgotten passwords. It also includes the steps for rebuilding an Apple Mail mailbox, which can fix problems with incorrect message counts or messages that won't display.

And it's a great guide to actually moving your email, should you ever need to do so.

What to Do When Mail Fails to Auto-Complete Email Addresses

Have you noticed that your Mac's Mail app has stopped automatically completing an email address when you enter it into any of the Mail header fields (To, CC, BCC)? Perhaps you've also noticed that Mail is no longer able to add events and invitations to your Calendar program.

It appears this may be a bug in how Mail transverses an alias to a cloud storage or syncing service. While Mail will work just fine with iCloud and its services, if you've decided to use Google Drive, Dropbox, or other cloud-based services, then you may run into this problem.

If you're using OS X Mountain Lion or later, we may have the fix you're looking for right here.

How to Filter Spam With Apple Mail to Keep the Junk Mail at Bay

Junk mail seems to plague just about every mail account I've ever created. It seems within a day of using a new mail account, the spammers will find the email address, and gleefully add it to their mailing list.

Of course, once you're on one spammer's mailing list, you're soon on everyone else's. That's why I like Mail's built-in system for dealing with junk mail.

Mail's junk mail filters work pretty well out of the box, but you can get much better spam recognition with just a few tweaks to the settings, and a bit of encouragement by telling the junk mail system which messages are correctly identified as spam and which ones aren't.

Spending a little bit of time with the junk mail filter can really make using Mail a better experience.

Getting iCloud Mail Working on Your Mac

iCloud Preference pane showing Mail set up

Coyote Moon, Inc.

iCloud offers a nice selection of cloud-based services for the Mac and iOS devices. They include syncing browser bookmarks, syncing login credentials, and an iCloud-based email system.

One of the nice features of iCloud Mail is that you don’t have to use the web-based interface to the mail system. Instead, you can use your Mac's Mail app and send and receive iCloud mail just like any other email account you may have.

Even better, setup is easy. Mail already knows most of the settings an iCloud mail account needs, so you won't need to search for obscure server names to get iCloud mail up and running.

How to Set Up Apple Mail Rules

Apple mail rule editor

Coyote Moon, Inc.

Apple Mail is popular and easy to set up and use, but one place that seems to invite trouble is setting up and using Apple Mail rules to automate the Mail app.

With properly configured Mail rules, you can have Mail sort your email messages, putting important messages in a must-answer-right-away mailbox. Likewise, messages from friends can be grouped together, and messages from annoying vendors you need to keep in contact with, but whose sales pitches you'd rather deal with on your schedule and not theirs, can be placed in an "I'll get around to it someday" mailbox.

Getting Apple Mail rules working correctly can really help your use of Apple Mail. Having Mail rules that don’t work correctly can cause all kinds of strange Apple Mail behavior that is often misdiagnosed as Mail not working.