Fix Mail Problems

As I said earlier in this book, the macOS version of Mail (at least in its Sierra and High Sierra incarnations) has a number of reliability and behavior problems, and many of them are things you can’t fix, because you didn’t do anything to cause them—only Apple can fix them. So, although I can’t offer solutions to every problem, I’ve compiled solutions to some of the most common (and serious) problems in the pages ahead, including difficulties receiving and sending mail, problems with damaged mailboxes, and misbehaving Spotlight searches.

Although some of this information may provide useful background for resolving iOS Mail issues too, the specifics are different; see Troubleshoot iOS Mail Problems for help with Mail in iOS.

Fix Incoming Mail Problems

If Mail cannot download incoming messages, the cause may be anything from an incorrect setting in Mail, to a server problem, to a loss of internet connectivity. Work through each of the following sections until you resolve the problem.

Try Connection Doctor

To open Connection Doctor, choose Window > Connection Doctor. In the Connection Doctor window, Mail lists each incoming and outgoing email account you’ve configured—even those you’ve temporarily disabled. It attempts to log in to each account, and if it fails with any of them, it shows an explanation of why it failed. These explanations aren’t always helpful, but they often give you a good starting point in debugging problems, and are written in refreshingly plain English. If the Connection Doctor window suggests a specific fix, try that first. Otherwise, proceed with the following steps.

Username and Password Errors

If you enter your password in Mail > Preferences > Accounts (or in System Preferences > Internet Accounts), macOS stores the password in your keychain (which is usually what you want). If, for security reasons, you prefer for Mail to prompt you for your password each time you connect, leave the Password field blank.

Sometimes, even after successfully checking your email many times with the password you entered, Mail displays a dialog claiming that the mail server has “rejected” your password. Worse, you may re-enter your password—and even select “Remember this password in my keychain”—but find that another error message pops up as soon as you click OK. This annoyance may be due to any number of causes, but most have simple solutions.

If Mail suddenly begins prompting you for your password repeatedly when checking incoming mail (after retrieving it correctly earlier), try these steps in order until the problem goes away:

  1. Click Cancel, and then check your email again in a minute or two. Sometimes the problem goes away on its own—most likely because the problem was on the mail server’s end or with the connection to the server. (If your account is offline, choose Mailbox > Take All Accounts Online.)

  2. If the problem persists, return to Keychain Access. Make sure that Passwords or All Items is selected under Category, locate your mail server in the list (for iCloud accounts, the entry’s name should show the Apple ID you use for iCloud and its type should be “application password”), select it, and click Delete. The next time you check your email, you’ll be prompted for your password; enter it, select “Remember this password in my keychain,” and click OK.

  3. If even that doesn’t work, your mail server may be at fault. Try checking your messages with another email client. If the other client also gives you error messages, ask your email provider for help.

Connection Errors

Sometimes, when attempting to contact a mail server, Mail encounters an error of one kind or another that prevents it from connecting. If you see a lightning bolt symbol, which I call a “squiggle,” next to an account name in your sidebar, that account is offline (not connected to the mail server). If Mail cannot connect to an account after multiple attempts, it takes the account offline automatically. This may be an indication that your computer as a whole is having internet connection issues; if so, you may also see this symbol on the right of the Favorites bar, with a message such as Network Offline. Or, it may be a problem with just that mail server, or with your settings for that account.

If you encounter a squiggle, follow these steps:

  1. Check your Internet connection: Visit your favorite website to make sure your computer can access the Internet. If it can’t, the problem relates to a failed Internet connection. If it can, continue with the next step.

  2. Try bringing your accounts online manually: To reestablish a connection, click the squiggle symbol next to an account name. Sometimes this jogs the connection back to life. If the account remains offline, continue to the next step.

  3. Disable automatic setting detection: I describe this option in the sidebar Automatic Setting Detection, just ahead—note that it doesn’t apply to account types such as iCloud, Gmail, and AOL. Having done this, check your password (in Mail > Preferences > Accounts > Account Name > Server Settings) and authentication method (in the same place, but only visible if you deselect “Automatically manage account settings”). Then close the Preferences window and click Save when prompted.

  4. Check mail server availability: Mail servers occasionally crash or become unreachable due to network problems. If an account remains offline even after you complete the preceding steps, contact your email provider to see if there’s a problem.

Fix Outgoing Mail (SMTP) Problems

One of the most frequently reported problems with Mail is an inability to send messages—after clicking the Send button, an error message appears. Rather than go into every detail about the many possible causes, symptoms, and solutions, I want to focus on just four central points. If you get an error when sending mail, most likely the reason is one of the following:

  • You have the wrong SMTP server (or no SMTP server) selected.

  • You have incorrect settings for the right SMTP server.

  • Your ISP is blocking the port Mail wants to use.

  • The SMTP server doesn’t respond quickly enough.

In all these cases, the solution is usually to make sure you know the correct settings and then enter them in the proper places.

Find the Correct Settings

When you initially set up your email account, your email provider typically provides you with a short list of information you’d need to access your account, including some or all of these details:

  • Your username, password, and email address

  • Addresses for the incoming (POP, IMAP, or Exchange) mail server and the outgoing (SMTP) server

  • Whether the incoming and/or outgoing servers use SSL (secure sockets layer, which encrypts email in transit)

  • You may also have received the following information:

    • What authentication method the servers use to verify your identity (for example, Password, MD5 Challenge-Response, or Kerberos)

    • What port(s) the incoming and outgoing servers can use

You’ll need all this information now. If you can’t find it in your records or on your email provider’s website, contact their customer service department for assistance.

Fix the “Wrong Server” Problem

Each email account you’ve set up includes settings for a single SMTP server (except Exchange accounts, which use the same server for incoming and outgoing mail). If you have lots of accounts, Mail may have settings for lots of SMTP servers—including, perhaps, some that are outdated or broken. As a result, it’s easy to inadvertently select the wrong SMTP server. And sometimes, Mail can get confused and forget the SMTP server you previously associated with an account, with the result that it has no outgoing server selected at all. Here’s how to address both problems.

Clean Out Your SMTP Server List

First, get rid of any SMTP servers that aren’t being used. To do this:

  1. Go to Mail > Preferences > Accounts, select any account in the list on the left, and click Server Settings.

  2. From the Account pop-up menu under Outgoing Mail Server (SMTP) or, for certain account types, the Outgoing Mail Account pop-up menu, choose Edit SMTP Server List.

  3. In the list at the top, note the third column, In Use By Account. (You won’t see servers listed for some account types, including iCloud and Gmail.) If this column is blank for any item in the list, select that item and click the minus button to remove it (confirming the deletion if prompted to do so). Repeat this step for every server not in use.

  4. Click OK.

Associate the Right Server with Each Account

Next, make sure every (incoming) email account uses the correct outgoing server. Follow these steps:

  1. Go to Mail > Preferences > Accounts, select an account in the list on the left, and click Server Settings.

  2. In the Account pop-up menu under Outgoing Mail Server (SMTP) or the Outgoing Mail Account pop-up menu, verify that a server is listed (None is always the wrong choice) and that the selected server is the one matching this incoming account. If the server appears to be correct but you’re still getting errors when sending mail, proceed with…

  3. From the Account pop-up menu under Outgoing Mail Server (SMTP) or the Outgoing Mail Account pop-up menu, choose Edit SMTP Server List.

  4. In the list at the top, make sure the SMTP server that was selected for the account is still selected, and click the minus button to remove it (confirming the deletion if prompted to do so).

  5. Click the plus button to add a new SMTP server. Fill in both the Account Information and Advanced views with the information you got from your email provider.

  6. Click OK.

Repeat these steps for all your accounts.

Now, choose Window > Connection Doctor, and wait for it to complete its checks. Next to the SMTP server you just modified, if you see a green dot (on the left) and the text (on the right) “Connection and login to server succeeded,” the change worked. If not, go on to…

Fix the “Incorrect Settings” Problem

Your SMTP server typically requires several settings to be exactly correct: your email address, username, and password; the server’s address; the port; the authentication method; and the SSL setting (on or off). If any one of these is wrong, you won’t be able to send mail.

Unfortunately, Mail’s error messages don’t always clarify which setting might be incorrect. So, if an error message doesn’t provide an obvious solution, do this:

  1. Go to Mail > Preferences > Accounts > Account Name > Server Settings.

  2. Confirm that the correct SMTP server is already selected in the Account pop-up menu under Outgoing Mail Server (SMTP) or the Outgoing Mail Account pop-up menu. If that menu is the only thing in the Server Settings view (as it is for certain account types, including iCloud and Gmail), skip the remaining steps.

  3. Confirm that the User Name, Password, Host Name fields are filled with exactly what your email provider specified. Note that some email providers expect you to use your entire email address as the User Name, and that the host name is typically something like smtp.domain.com.

  4. If the “Automatically manage connection settings” checkbox appears under Outgoing Mail Server (SMTP), uncheck it (see the sidebar Automatic Setting Detection for details).

  5. Confirm that the server port, Use Secure Sockets Layer (SSL)TLS/SSL checkbox, and authentication method, username, and password exactly match what your email provider specified. If any of these items is incorrect, correct the information and click OK. (Note that some email providers expect you to use your entire email address as the username.). Click Save.

    Now, choose Window > Connection Doctor, and wait for it to complete its checks. Next to the SMTP server you just modified, if you see a green dot (on the left) and the text (on the right) “Connection and login to server succeeded,” the change worked.

    If the change did not work, proceed with:

  6. Return to the Server Settings view from Step 5 just previously. Choose a different authentication method, click Save, and repeat the check in Connection Doctor. Repeat this step up to five times, trying each method (including None) in turn. If that doesn’t work…

  7. Back in the Server Settings view, toggle the Use TLS/SSL checkbox, click Save, and repeat the check in Connection Doctor.

  8. If that doesn’t work, try the suggestions for fixing a blocked port, next.

Fix the “Blocked Port” Problem

Many ISPs routinely block the use of port 25—the “channel” most email programs use to send mail—except for email originating within that ISP’s network and sent via its own SMTP servers. For example, if you’re a Kabletown customer and connect via a cable modem from your home, you could send email via Kabletown’s SMTP server through port 25. But you probably couldn’t send mail using, say, smtp.gmail.com on port 25 (because that server is outside the network from which you’re connecting); similarly, if you take your laptop to a coffee shop, whose network service is provided by another ISP, that network may block port 25, preventing you from reaching your regular Kabletown SMTP server while you’re away from home.

Either way, the result is an error message when you try sending email from a particular account—even though you might be able to send from that account at another location, or from another account at your current location.

One way to solve this problem is to switch to a different port—one that isn’t blocked. For this to work, your email provider must support the use of the alternative port. To learn if they do, check their website or contact their technical support department…or just guess. The most commonly used alternative ports are 465 and 587, and if the “Automatically manage connection settings” checkbox is selected (as discussed previously), Mail in macOS tries these two ports automatically if port 25 doesn’t work.

However, if your provider uses a less-common port (such as 2525), you can enter that manually:

  1. Choose Mail > Preferences > Accounts > Account Name > Server Settings.

  2. Uncheck “Automatically manage connection settings” under Outgoing Mail Server (SMTP).

  3. Enter the port number (whatever your email provider tells you) in the Port field, and click Save.

Now, choose Window > Connection Doctor, and wait for it to complete its checks. Next to the SMTP server you just modified, if you see a green dot (on the left) and the text (on the right) “Connection and login to server succeeded,” all is well. If not, contact your email provider for assistance.

If no alternative port solves the problem, you have three options:

  • Use your email provider’s webmail interface to send mail until you return to your regular network.

  • Send your message from a different account in Mail, if one is available that doesn’t suffer from the port-blocking problem.

  • Use a virtual private network—such as those provided at modest cost by Private Internet Access (my top pick), IVPN (Wirecutter’s top pick), Encrypt.me, WiTopia, or the free Hotspot Shield service.

    A VPN makes it appear to remote servers as though your Mac is on a different network, not the one you’re actually connected to, and in most cases the VPN won’t block port 25. Once you connect your Mac to the internet using one of these services, you should be able to send email on whichever port you normally use.

Fix Sending Delays

Error messages aren’t the only problems that can arise when sending mail. Sometimes Mail succeeds in sending your messages, but only after what seems like an interminable delay—perhaps 30 seconds or longer for each outgoing message.

One likely cause of this problem is that macOS is taking too long to do a DNS lookup. This problem, in turn, often occurs when your ISP doesn’t provide any explicit addresses for its DNS servers, but rather supplies them dynamically using DHCP (dynamic host configuration protocol), the same method by which your computer probably gets its IP address. The upshot is that when Mail tries to send, it might have to query several servers in a row (waiting for each to respond) to figure out how to talk to the SMTP server.

The best way to solve this problem is to stop relying on your ISP to dynamically supply the addresses of its (possibly slow) DNS servers. Using a free service called 1.1.1.1, you can override your default (dynamic or blank) DNS server list with the static addresses of speedy, reliable DNS servers.

To use 1.1.1.1, follow these steps:

  1. Go to System Preferences > Network.

  2. If the lock icon in the lower left corner of the window is in its locked state, click it and enter your administrator credentials to unlock it.

  3. In the list on the left, select the interface that’s currently providing your internet access (usually AirPort or Built-in Ethernet).

  4. Click Advanced, and then click DNS.

  5. Under the DNS Server field, click the plus button, type 1.1.1.1, and press Return. Then repeat this step using the address 1.0.0.1. Click OK.

  6. Click Apply, and then close System Preferences.

  7. To verify that the new DNS servers are working, visit any website in your favorite browser.

If DNS delays were causing the sending problem, sending mail should go much faster now.

Untangle Special Mailboxes

Because each mail server handles Special Mailboxes slightly differently, you may find that Mail isn’t using the mailbox you expect for Drafts, Sent, Trash, Junk, and/or Archive. If you have problems—such as more than one special mailbox for a given category appearing in a single account—these instructions may help.

I’ll use Sent here, but this process is similar for any special mailbox:

  1. Go to Mail > Preferences > Accounts > Account Name > Mailbox Behaviors, where Account Name is the one with the duplicate mailboxes.

  2. From the Sent Mailbox pop-up menu, choose Sent under On My Mac. Then close the Preferences window.

  3. In Mail’s sidebar, look in the list of mailboxes for the account in question. A new mailbox should have appeared in that list—that’s the one Mail was using for Sent in that account until a moment ago; you’ve just relocated it from the server to your Mac. You’ll also see the existing duplicate mailbox(es), such as Sent.

  4. Decide which mailbox you want to be the “real” Sent mailbox. The best way to do this is to send a message from the email account’s webmail interface—not from within Mail—and see which mailbox it goes into.

  5. Whichever mailbox you identified in the previous step, go back to Mail > Preferences > Accounts > Account Name > Mailbox Behaviors and select that mailbox from the Sent Mailbox pop-up menu (remembering that the mailbox is listed under your account name, not under On My Mac). Then close the Preferences window.

  6. Now go to the other Sent (or Sent Messages or whatever) mailbox that’s still listed under that account in the sidebar. Select all the messages in it and drag them to the Sent mailbox for that account under the unified Sent mailbox.

  7. Wait until all the messages have finished copying (use the mini activity monitor at the bottom of the sidebar or Window > Activity to keep an eye on your progress). Then select the now-empty mailbox whose contents you just moved, choose Mailbox > Delete Mailbox, and click Delete to confirm.

From now on, you shouldn’t be troubled by duplicate mailboxes. (Remember, you can follow almost exactly the same steps for other special mailboxes, such as Trash.)

Fix Mailbox Problems

Most of the time, Mail correctly displays all the messages in a mailbox when you select that mailbox. If your mailboxes begin misbehaving, though—not showing messages you know they contain or taking an extremely long time to show their contents, for example, you can try some easy tricks to fix them.

If your envelope index—a special database that Mail uses to track which messages are in which mailboxes—and the other files that Mail uses to catalog messages become damaged, Mail may exhibit any of several symptoms, including:

  • Missing messages

  • Incorrect message counts, in which the number of unread messages shown next to the mailbox name in the sidebar differs from the number of unread messages you see inside the mailbox

  • An empty mailbox, even though you know it contains messages

  • Failure to move messages into a mailbox (manually or using rules)

If you suspect that a mailbox contains errors, the standard cure-all is to rebuild it. To do this, select the mailbox (or mailboxes, by holding down the Shift key and clicking them) and choose Mailbox > Rebuild.

If that doesn’t solve the problem, quit Mail, navigate to ~/Library/Mail/V5/MailData (for High Sierra) or ~/Library/Mail/V4/MailData (for Sierra) and drag the files Envelope Index, Envelope Index-shm, and Envelope Index-wal to the Trash. When you launch Mail again, it’ll tell you that you need to “import” all your messages (just as it may have done when you upgraded to your current version of macOS). Let it do so—it’s recreating your envelope index from scratch, but don’t worry, you won’t lose any messages, labels, message status, or other data—and when it finishes, your mailboxes should behave correctly.

Fix Searching Errors

If searches in Mail fail blatantly (such as no results appearing for a very common term or hundreds of irrelevant results showing up for a search), even after rebuilding the envelope index, try each of these things, in order, until the problem goes away:

  1. Make sure that neither the folder ~/Library/Mail nor any of its parent folders is in Spotlight’s Privacy list (in System Preferences > Spotlight > Privacy).

  2. You may have server-hosted mailboxes whose contents have not yet been downloaded to your computer. To ensure that they have been, choose Mailbox > Synchronize Account-Name. If more than one account is configured, the account names appear on a Synchronize submenu, but you can choose Mailbox > Synchronize All Accounts to sync everything at once. Either way, this may take some time.

  3. Open /Applications/Utilities/Terminal and enter the following command, followed by Return, to re-index your Mail messages:

    mdimport -r /System/Library/Spotlight/Mail.mdimporter

  4. Still no luck? Trash your entire Spotlight index and allow Spotlight to rebuild it from scratch. In Terminal, type:

    sudo mdutil -E /

    Press Return and enter your administrator password when prompted. The rebuilding process goes on in the background, but may take several hours. When it’s finished, searching should work. But, fair warning: this is Spotlight we’re talking about. It has been notoriously flaky since it first appeared, and sometimes it just doesn’t work.

Deal with Recovered Messages

In the On My Mac portion of Mail’s sidebar, you may see a Recovered Messages mailbox. In fact, you may see more than one, each labeled with a different account name (like “Recovered Messages (iCloud)”). What are these weird mailboxes all about and what can you do to get rid of them?

One reason you might have such a mailbox is that you’ve used Time Machine to restore messages from a backup. For reasons that have never been clear to me, Mail doesn’t put these messages back where they came from, but rather creates this new, local mailbox and stores them there.

Mail also creates a mailbox like this and puts a message into it if it thinks the message might otherwise be lost. For example, if you’re in the process of moving a message and Mail crashes, or loses its connection to the server, or you shut down your Mac, the message can end up in “limbo”—you’ve already removed it from its original mailbox but it hasn’t reached its destination yet. There are various other situations in which Mail puts messages in Recovered Messages, but they all amount to the same thing: Apple is trying to be helpful by making sure a message that might otherwise disappear isn’t gone forever.

And yet…nearly every time I see a message in a Recovered Messages mailbox, it’s a duplicate of a message stored somewhere else. Mail never tells me why a message was moved there, what to do about it, or how to prevent the problem in the future. And, even after cleaning out my Recovered Messages mailbox(es) and deleting them, they always return.

So, although these steps may be ultimately unsatisfying, here’s what I suggest doing if you see a Recovered Messages mailbox:

  1. Select the mailbox in Mail’s sidebar.

  2. Manually move each of the messages in the mailbox to the place you think they should be stored (or delete them, if you don’t need them).

  3. Keeping an eye on the progress indicator at the bottom of the sidebar, wait until all the messages have finished copying.

  4. Once the Recovered Messages mailbox is empty, delete it by selecting, choosing Mailbox > Delete Mailbox, and clicking Delete.

If you have more than one Recovered Messages mailbox, repeat the above steps for each.

But keep in mind:

  • The messages you moved might be duplicates of messages you already have. If that bothers you, you can manually delete one of the duplicates, but I personally feel that’s more trouble than it’s worth.

  • You might wake up tomorrow to find that Recovered Messages mailbox back again!

Solve Other Problems

Besides what I’ve covered so far in this chapter, there are tons of other problems you may encounter in Mail. At the risk of repeating myself, in almost every case, it’s not you, it’s Apple.

And, just to head off the inevitable email messages that begin, “Yeah, but what about…” let me be clear: if Mail is doing something you don’t like and this book doesn’t contain a solution—or if my proposed solution doesn’t work for you—I’m sorry to say I have nothing further to offer (and I’m probably frustrated with the same problem myself). Everything I know about Mail comes from either trial and error or reading what other people have tried—and there’s nothing more in my bag of tricks than what’s in this book. I also have no inside connections on the Mail team at Apple, and no influence over Mail’s development. So, if you ask me about any other problem, all I can suggest is to consult Apple’s Mail support page or do a web search. Sorry!

That said, if you find a solution to a Mail problem that was vexing you, I’d love to hear about it! Please let me know, and perhaps I’ll include that information in a future version of this book.

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