Kibbles and Bytes

Troubleshooting eMail Problems

Written by Don Mayer | Jun 18, 2020 4:04:57 PM

One of the most common questions we are asked is "Help, my eMail is not working..." of "Help, I cannot send eMail" or "Help, my eMail disappeared.." . Troubleshooting these eMail issues is complicated by the myriad of eMail clients, servers and accounts as well as issues of connectivity unrelated to eMail.

When a friend calls with eMail issues, my first question is always - "do you have internet?" and I ask them to go to Safari and try to surf to a website that they do not normally visit (to avoid any caching issues).  If they have connectivity we can move to diagnose eMail issues.   If connectivity is the issue we go through the steps of restarting the radios on the Mac, iPad or iPhone by putting them in Airplane mode and taking them off.  Then we may try restarting the device, investigating whether the internet service provider is having a downtime and restarting the modem or router.

But if they successfully surf to the random website that I give them, perhaps my favorite restaurant or lefty political news site, we have to look at other issues to address mail.  Mail servers go down and it is pretty simple to determine if your server is down. That is usually not the problem.

If you are not receiving eMail here are some suggestions of steps to try:

  • Check whether Mail is retrieving a large message or a message with large attachments. You can choose the "Activity" menu item to see if it is hung up on that 500MB download.
  • Check if you’re using filters in the message list that are preventing expected messages from being shown.
  • Try sorting messages in the message list by Date or another attribute, or searching for messages, to verify if you received them.
  • Check whether your account is offline or disabled (inactive).
  • If you’re missing emails from a specific person or group, check whether you blocked messages from them.
  • Try quitting Mail, then opening it again.
  • Choose Window > Connection Doctor, then follow any instructions in the Details column. Check for problems logging in to email accounts or with the incoming mail server, or with firewall software blocking network traffic.

    Check whether you’re affected by another firewall, such as software installed separately from macOS or built into an internet sharing router, or administered by your email account provider.

  • If you’re still having problems, contact your email account provider to verify your user name, password, incoming mail server, and other required information. Then verify the information is entered correctly in Mail account preferences.

Many email providers offer webmail, which is a way to use email with a web browser such as Safari, instead of with an email app such as Mail. For example, if you're using an iCloud Mail account, you can use iCloud.com to send and receive email, if you use Gmail you can use gmail.com or if you are wicked old and still have an AOL account - get a new account!

Webmail is a good way to verify that your account is valid and you can sign in to it from the web, but it doesn't mean that your account is set up correctly in Mail. If a mail server doesn’t accept your user name and password, try these suggestions.

Not receiving?

You might see a status icon such as a lightning bolt or warning symbol next to your account's inbox in the Mail sidebar, or in the upper-right corner of the Mail window. Click it to learn more.

  • If the status is Network Offline, make sure that your Mac is connected to the Internet, then try again.
  • If the status is Login Failed, check with your email provider to be sure that your account is set up correctly on your Mac.
  • If Mail asks for your password, but entering the password doesn't help, find out why your email provider is rejecting your password.
  • If your email service is temporarily unavailable, your email provider might have a status message on their website. For example, Apple's system status page shows the status of iCloud Mail. Status pages are also available for other email services, such as Gmail and Outlook. Some brief service outages might not appear on a system status page, so you might want to wait a few hours and try again.

In the Mail app on your Mac or your eMail client, do the following:

  • Make sure you enter the password for your email account, not the login password for your Mac or the password for another account.
  • Make sure you enter uppercase and lowercase characters where needed.
  • Verify your login information. Choose Mail > Preferences, then click Accounts.

If people tell you that they are not receiving your emails you can try these steps:

  • Make sure the person’s email address is correct. Ask the person to send you a message, then reply to it. Now the email address is in the Previous Recipients list in Mail and should be correct.
  • Some mail servers reject messages that exceed a certain size. If your message includes attachments, use Mail Drop or try resizing image attachments.
  • Send yourself a test message. If you receive it, ask people to send themselves a test message to see if the mail server for their email accounts has a problem.
  • Use Connection Doctor to check your network connection.
  • Ask your email account provider whether it limits the number of people you can send a message to at one time, as a way to prevent junk mail.
  • Some mail servers won’t deliver a message to any of the recipients if even one address is invalid. When this happens, Mail alerts you that the message wasn’t sent. Open the message (it’s in your Outbox) and remove or correct invalid addresses, then send the message again.

If you have just gotten a new Mac or iPhone and are setting up eMail for the first time, realize that it does take some time for the device to download your messages from the server, especially if they contain large attachments such as pictures or videos.

As I think about the hundreds of calls about "no eMail!" I think that the top causes are:

  1. No internet connection
  2. Mail is hung up on a gigantic download
  3. eMail provider has a temporary outage
  4. eMail client settings are wrong