5 Simple Steps to Fix Email Problems on Mac, iPhone or PC

Last Updated: Dec 06, 2022

Written by

This article contains affiliate links, which means that I may receive a commission if you make a purchase using these links.

Here are five simple steps you can take if you’re unable to send emails, if you’re unable to receive emails, or if you’re unable to delete emails on your Mac, iPhone, iPad, Android phone or Windows PC.

Even though I’m using macOS and iOS as examples, you can apply most of the solutions I describe in this article to fix email problems on Windows and Android.

One of the most common computer problems friends and relatives complain about is related to sending and receiving email.

I have also run into many issues with iOS and Exchange/Office365 accounts related to ghost messages that won’t disappear from my email inbox. When I try to remove those ghosts, I get an error message that says “Unable to Move Message.”

The troubleshooting steps I go through (and that I make others go through) are almost always the same, and so I decided to write them down. The next time someone asks me for help with email problems, I’ll refer them to this article.

Apple Mail unable to send emails
Apple Mail is unable to send an email.

In this article, I’m using Apple Mail on macOS 10.13 and the native Mail app on iOS 11 to illustrate the most common problems and their solutions. But if you’re using Microsoft Outlook or another email client, note that most of the steps below still apply. The dialog box or error messages might look slightly different or have different wording, but the underlying errors tend to be the same.

Common Email Problems

If you found this page on Google because you were looking for a solution to any of the following problems, chances are that the email troubleshooting steps below will fix your issues. So stick with me!

  • Why can’t I get my emails on my iPhone
  • Why is my email not working on my iPhone
  • Can send but not receive emails?
  • Can receive but not send emails?
  • I can receive but cannot send emails on iPhone
  • Unable to send email from iPad
  • Unable to send email phone
  • Cannot send email from iPhone username or password incorrect
  • Can no longer send email from iPhone?
  • Can’t send emails from iPhone but can receive them
  • Why is my email not working on my computer?

The Most Common Causes of Email Issues

Not being able to send or receive emails can be a major inconvenience, especially if you rely on email for your job or business. The good news is that most email problems have causes that are easy to fix, including:

  • A wrong or expired email password
  • Incorrect account settings (server address, port number or protocol)
  • A misbehaving email client or email app

5 Steps to Fix Common Email Problems

5 Simple steps to fix email problems on Mac and iPhone
iOS is unable to receive emails.

If you’re unable to send or receive emails, take a deep breath and follow the steps below. I highly recommend not skipping any of the steps, even if you feel convinced that (for example) your email password isn’t the culprit. I consider myself proficient with technology, but even I have spent time debugging an email problem that was ultimately caused by an expired password.

Had I checked the validity of my password first, I could have saved the time I wasted trying to figure out the problem. To ensure you’re not mistyping the password, which is particularly easy to do on a mobile device, I recommend copying and pasting the password from a password manager, such as 1Password.

The five steps I recommend following are:

  1. Verify your email account password
  2. Verify your email account username
  3. Determine the email account type
  4. Check the email server connection settings
  5. Fix a misbehaving email program or app

Step 1 – Verify Your Email Account Password

Before you do anything else, double check to make sure you have the correct password and that it hasn’t expired. The best way to do that is by logging in to your email account via your provider’s web-based email system. Logging in via your web browser can tell you whether the problem you’re experiencing exists at the account level or the program/app level.

If you use Gmail, go to gmail.com and try to log in. If you use a different service provider, find out what their web-based email system’s url is. Often, it’s something like webmail.provider.com. For example, with Bluehost, go to webmail.bluehost.com and sign on to your account.

Bluehost webmail control panel
Log in to the Bluehost webmail control panel.

If you can’t log in via your web browser, chances are you’re using an incorrect username or password. If you cant figure out your username, try your email address. If you can’t figure out the correct password, try to reset it. Once you’ve done that, make sure you save it in a password manager (such as 1Password). That way, you won’t forget it again. But don’t use an easy-to-guess password, just because you are afraid of forgetting it!

If you use Microsoft Exchange, Office 365, or an Outlook account for your email, and the webmail interface prompts you to change your password, you know that your old password had expired. I use Office 365 for work and I have to change my password every three months because of my company’s password expiration policy.

If your email provider doesn’t offer a webmail client, try to send and receive a test email from another device (assuming you have another device and your email account is set up on it). Again, this troubleshooting step is designed to let you know whether the problem is with one particular device or your account settings and configuration.

If you can log in to webmail or from a secondary device successfully, but sending email or receiving email still fails on your primary device, proceed to the next steps.

Note: Fixing an incorrect, forgotten or expired password is easy. But don’t worry — verifying and correcting wrong account settings isn’t complicated either. Just follow these steps and you’ll be up and running in no time.

Step 2 – Verify Your Email Account Username

Depending on your email service provider, your username could be your email address, a part thereof, or something entirely different.

I use Office 365 as the email service for my blog. As a result, my username is the same as my email address: [email protected]. Bluehost also uses your email address as the default username for its email accounts.

If you’re trying to set up your email account on a new device — after having gotten a new iPhone, for example — make sure your username is correct. The easiest way to do that is to verify if you can log in via webmail (see Step 1). I have seen many people use the correct password but the wrong username, so always double check if you’re using the correct account credentials!

Step 3 – Determine the Email Account Type

Depending on the type of email account you have, the next steps might vary from the screenshots below. Common account types include:

  • IMAP
  • Exchange
  • POP3

Popular email providers like Google and Apple use a variation of the IMAP protocol to receive emails. For business accounts, or if you use Office 365, you’re likely dealing with an Exchange Server account. And some internet service providers (ISPs) still offer the old and outdated POP3 protocol.

If that’s what you use, I highly recommend checking to see if your email service provider supports using an IMAP account instead. It offers a ton of advantages over POP3 (such as better message syncing).

When it comes to sending email, SMTP is the most common protocol (unless you use an Exchange Server). To figure out what account type you have, follow these steps:

On macOS:

  • Open Mail and go to Mail > Preferences (or press Command + ,)
  • Go to Accounts and verify the account type underneath the account name, in the left section of the dialog box

In the screenshot below, you can see two IMAP accounts (an iCloud email account and a test email account) and three Exchange accounts.

Apple Mail Email settings Office 365
Apple Mail settings: Accounts.

On iOS:

  • Open the Settings app and go to Accounts & Passwords
  • Click on the account you want to verify
  • You can see the account type on top of the screen (see Exchange in the screenshot below)
iOS email account type exchange
iOS > Account Type – Exchange.

Step 4 – Check the Email Server Connection Settings

Once you’ve determined your email account type, the next step is to verify your incoming server settings. If you’re receiving email but having trouble sending an email, then you can skip to the next step to check your outgoing server settings!

Both macOS and iOS usually manage the server connection settings automatically for most account types, especially Exchange accounts. In fact, for Exchange accounts, the only connection settings you can tweak on macOS are the Internal and External URL.

For Office 365, like in the example below, both URLs point to https://outlook.office365.com/EWS/Exchange.asmx. If you can’t see those two URLs, just uncheck “Automatically manage connection settings” on the Accounts tab.

Beyond that, there isn’t usually much to verify with Exchange accounts (unless your email provider uses an old version of Microsoft Exchange).

Apple Mail Office 365 server URLs
Office 365 account server settings.

When it comes to IMAP accounts, both macOS and iOS have become pretty good at automatically managing connection settings. In the example below, I have set up an IMAP account with Bluehost. MacOS automatically determined the proper parameters when I initially set up the account in the native Mail app.

But if you have an older version of Apple’s operating system, or if the OS can’t determine the correct settings automatically, you may have to change them manually.

Incoming Mail Server

To check the details of your incoming mail server settings, you may have to uncheck “Automatically manage connection settings” under Incoming Mail Server (IMAP).

Apple Mail IMAP mail server settings
Apple Mail: incoming and outgoing server settings.

Once you’ve done that, you’ll see additional connection settings, including:

  • Port
  • Use TLS/SSL
  • Authentication

Before you proceed, double check to make sure the username, password and hostname are correct. In my example, I have to use the following basic settings:

Bluehost, like many other email service providers, may give you confusing information regarding the proper hostname to use. Normally, the hostname of the email server would be similar to your email domain (i.e., gmail.com, or eventosdeportivos.com).

So you may be inclined to think that the incoming mail server should (in my case) be eventosdeportivos.com or imap.eventosdeportivos.com.

I’m using encrypted communication via TLS/SSL, and I don’t have my own SSL certificate. That’s why I have to use box930.bluehost.com — because it matches the SSL certificate that Bluehost provides for my web host.

The standard IMAP port is 143, but with SSL it’s 993. As you can see in the screenshot, macOS put the non-secure 143 port into the connection settings. Given that, you might think that I’m using an incorrect port number and that switching them out will resolve the issue.

However, both Apple Mail and the Bluehost IMAP server support transport layer security (TLS), which can automatically hand over from an insecure channel (port 143) to an encrypted channel (port 993).

The caveat is that if your IMAP server doesn’t speak TLS and only supports SSL, make sure you change the port to 993 if Apple Mail doesn’t do that automatically.

Note: Enabling SSL/TLS but using the insecure default port (143) is one of the most common problems I have seen.

To verify the connection settings on iOS, follow these steps:

  • Open the Settings app
  • Click on the account you want to verify
  • Click on the Account field
  • Go to Advanced on the bottom of the screen
  • Scroll down to Incoming Settings

Under Incoming Settings, make sure you have “Use SSL” checked, unless your provider doesn’t support it. If so, I’d look for another provider! Check that the authentication is set to “Password,” and double check the server port. With SSL enabled, the port should be 993 for IMAP accounts because the Mail app on iOS doesn’t support TLS!

iOS email account settings for incoming (IMAP) mail server
iOS > Incoming mail server settings (IMAP).

Outgoing Mail Server

If receiving email is working fine, but you’re having problems sending email, follow these steps to verify and fix the outgoing server settings.

On macOS, follow the same steps as above and verify that your username, password, hostname, and port are correct.

The most common issue that causes problems sending email is an incorrect port number. For SMTP the standard port for unencrypted (insecure) communication is 25, but I don’t recommend using that. For the more secure SMTPS (SMTP over SSL), the default port is 587.

Note: Bluehost says in its documentation that they use port 465 for SMTPS, but in my tests both 465 and 587 worked.

Additionally, make sure that you have the proper account selected under Outgoing Mail Server (SMTP). Apple Mail tends to forget what outgoing mail server it’s supposed to use. I wrote about that problem in another blog post.

To verify your outgoing mail connection settings on iOS, follow these steps:

  • Open the Settings app
  • Click on the account you want to verify
  • Click on the Account field
  • Go to SMTP under Outgoing Mail Server
  • Select the primary server

Then verify if the server is enabled and all settings look correct, especially “Use SSL” and the corresponding server port.

iOS account settings for outgoing (smtp) mail server
iOS > Outgoing mail server settings (SMTP).

Step 5 – Fix a Misbehaving Email Program or App

Sometimes your email client may run into an issue and forget the connection settings, or try to use a cached but expired password. In those cases, the best course of action is to quit the app and start it back up.

To quit an app on macOS, just right click on the app icon in the Dock and select “Quit.” If it doesn’t want to quit, hold the Option key and right-click to force quit the app (which works like CTRL + ALT + DELETE on Windows).

On iOS devices with a home button, double-click the home button and swipe up to remove the Mail app from memory. If you have an iPhone without a home button, such as the iPhone X, swipe up from the bottom and stop halfway to bring up the app switcher.

Then touch and hold the Mail app until you see the red “quit” circle in the upper-left corner of the app. From there, press the red icon or swipe up on the app to shut it down.

Note: Quitting apps on iOS is normally not recommended or necessary unless the app crashes. I still see many iOS users making it a habit of periodically closing all their apps, hoping to save battery (or for other reasons). Apple has been very clear on why that’s useless.

Additional Email Troubleshooting

If the above steps don’t resolve your email issues, there are a few more steps you can take to troubleshoot the problem further.

Temporarily Disable the Mail Account

Internet Accounts in System Preferences
Internet Accounts in the MacOS System Preferences.

Before we look at advanced techniques, one of the easiest ways to fix an issue is to remove and re-add the account.

On MacOS – System Preferences

Depending on the type of email account (iCloud email or other), open System Preferences and go to iCloud or Internet Accounts. You have to pick the latter if the affected account is part of iCloud. From there, merely unselect Mail, close the Mail app, re-enable Mail under System Preferences and open/re-launch Mail.

On iOS – Settings

The steps on iOS are similar, but instead of going into System Preferences, you open the Settings app and scroll down to Passwords & Accounts. From there, you can select the affected account type and disable/re-enable Mail.

Delete and Re-Add the Mail Account

If flipping the switch as described above doesn’t work, you might have to delete the entire account and re-add it.

Analyze Log Files

In Apple Mail, go to Window > Connection Doctor and see if your account shows an error. If it does, you can select “Log Connection Activity” and click on “Check Again.”

Apple Mail Connection Doctor
Apple Mail > Connection Doctor.

Once Apple Mail has completed the check, click on “Show Logs” and look for the log file that matches your server name. You should see two files per server name: one for the incoming connection and one for the outgoing connection.

Apple Mail Finder location of diagnostics files
Apple Mail > Diagnostics files in Finder.

Open both files and look for the reason why the connection attempt failed. In my case, I could see that the problem was related to an incorrect password.

Apple Mail Diagnostics file
Apple Mail > Diagnostics file.

If you don’t know how to read or interpret the log data, you can send it to Apple Support when you contact them for further assistance.

Unable to Delete Emails on iOS

A few months ago, I started seeing issues related to ghosts messages. Those are emails that I had already deleted or archived that wouldn’t disappear from my mailbox. If I tried to delete or move them again on the affected iPhone or iPad, I would get error messages saying “Unable to Move Message.” Over time, those ghosts messages would start to really clutter up my mailbox.

After doing some research, I realized that this is one of the most common iPhone email problems. And fortunately, there’s a way to resolve the issue. The most obvious solution is to completely remove and re-add the affected email account, which is what I would recommend.

Another, albeit potentially temporary solution, is to kill the Mail app, go into Settings > Passwords & Accounts, and disable Mail from the affected account by flipping the switch. Then relaunch the Mail app and confirm that all the ghost messages have finally moved on to their final resting place in the infinite cloud.

If that’s the case, re-enable Mail on the impacted account. I had to do this a couple of times before it worked. And in some cases, the problem returned a few days or weeks later. I was haunted. As a result, I recommend completely removing the account and re-adding it.

Misbehaving Spam Filters

Apple’s email app has relatively poor spam filters. As a result, I disabled the junk mail filter in Apple Mail on my Macs. Unfortunately, if you use iCloud Mail, there’s an additional (server-side) spam folder that may mess with your email inbox by placing legit email messages into the trash.

To learn more about how to troubleshoot that issue, check out this article.

How to Fix Email Problems

Whether you’re unable to send emails or unable to receive emails, I hope the steps above helped you resolve the issue. Most of the email problems I have come across were related to a wrong or expired password, incorrect mail settings, or a misbehaving email client.

If none of the above steps resolved your issues, you can also try to remove the email account from your device completely and then re-add it. If you use Exchange or IMAP, you won’t lose any emails by doing that.

If you’re experiencing a different problem or have found another solution to fix email problems, leave a comment below. I may update the article accordingly!

77 thoughts on “5 Simple Steps to Fix Email Problems on Mac, iPhone or PC”

  1. Hi

    Could you please assist me! I am able to receive my emails but I am unable to reply to them as it keeps saying “oops there if something wrong with the system” then after I will see a message saying “message could not be sent. Check your network and try again” what can I do to fix this problem?

    • Hi Pretty,

      Unfortunately, your issues could be caused by a million of reasons and finding out what the problem is remotely (via exchanging messages) is almost impossible. I’d take your computer or Mac to someone who can look at it. If it’s a Mac, try an Apple Store.


  2. Hi Michael,

    For some reason the Flagged mail box keeps disappearing. The messages still show as being flagged. In the past the Flagged mail box has come back but I don’t remember what I did. Please help.

    Thank you.

  3. Hi Michael,

    I am having issues with my mail on my Mac. It is constantly saying mailbox is full even though very minimal emails are in the inbox. How can I resolve this? I am not receiving emails due to this. Any information is appreciated.


    • Your mailbox consists of more than your Inbox. It also includes your Sent and Archive folders, Deleted Items, etc. I’m guessing one of these other folders has filled up and needs to be emptied.

  4. Hi Michael,
    Thanks for the tips. I couldn’t see my issue so thought I would ask for help. My emails on my iPhone are working perfectly but not on my MacBook Pro computer. I have a very full inbox (thousands of emails) – don’t judge! My issue is that my computer is randomly missing thousands of emails (new emails see to come in fine) – which is about half of my emails missing on my computer that are fine on my iPhone! When I need access to an email on my computer my short term solution is to forward to my email from my phone then access on my computer when it goes through (pretty much straight away). Any ideas on how to solve for an untechy mum!

    • Hi MJ,

      you might have to close the Mail.app and then delete the account in System Preferences and also delete (make a backup copy first) ~/Library/Mail/V8.

      Then re-add the mail account and see if Mail fetches all of the old emails.


  5. Hi Michael,

    Is this any way to stop an Exchange acount from pushing email to my inbox? I use Apple Mail on a Macbook Pro, Catalina OS, and I have checked the “Check for new messages manually” box, but the mails still come pouring in immediately. I’m guessing this is something that can’t be changed with Exchange. I find it really disruptive not to be able to regulate when the emails come in.

    Thanks for any help you can provide.

    • Hi CJ,

      I’m not aware of any client-side setting to prevent Exchange from pushing emails. You could try using the IMAP interface if supported by your Exchange.


  6. Hi Michael,

    Set-up: MacBook Pro 13 mid 2012, Catalina 10.15.7, POP3 email on Mac Mail

    I get the dreaded triangle next to my account names and message: The server returned the error: Connections to the server …. on the default ports timed out.
    I can send emails without any problems, but can’t receive incoming correspondence.
    The problem stays for most of the day, but then suddenly disappear and I can catch up with the incoming mail.
    Re-starting Mail won’t help, but re-starting computer does, but not always.
    In the morning I usually see many emails downloaded overnight, but for most of the day I encounter the problem of not being able to receive messages.

  7. Hi Michael. I’m hoping that you can help. Nobody else has been able to yet. I use all Mac products. All updated to date. For some reason all email from my various domains thru Bluehost, won’t download in Apple mail while WiFi is on. This is on my MacBook Pro, iPhones, iPad, etc. everything. I’ve deleted and added all email accounts a few times and it didn’t make a difference. I reset network settings and it didn’t make a difference. I even reset my phone and it didn’t make a difference. This has been going on for a few months now and it’s really getting aggravating. Gmail and iCloud emails opened in Apple mail work fine. Any advice ?

    • Hi Vicky,

      please see my reply to another commenter with the same issue:

      My father-in-law also uses Bluehost and they changed the name of his server from box123 to box789 (not the actual server names but you know what I mean). That caused the credentials not to work anymore and the security warning. So I’d recommend to log into the Bluehost webmail interface and verify what the proper server name should be!

  8. My problem of not getting mail on my MacBook Pro turned out to be The Firewall was turned off.As soon as I turned it on no problem, back to normal!!!Hooray

  9. When I have all my emails showing on a list (hotmail.com), I’ll select one of the emails, take a look at it and decide I want to just have it return back down off the screen & back to my lists of emails without deleting it. There used to be a Big X on top of the sliding bar on the right hand side where I would just click the Big X and it would do so. That X is no longer showing so my only option is to go to previous or next email or delete it. I’M JUST WANTING TO SAVE IT BY CLICKING THE BIG X AND HAVE THAT EMAIL GO BACK DOWN TO ALL MY OTHER EMAILS THAT ARE LISTED. How to I get that big X to appear again?

  10. Thanks for this great advice. My problem recently is that all my emails under bluehost account stopped working and when I decided to delete them at add them again, It says “unable to verify username and password” and when I manually typed in my bluehost hosting box240.bluehost.com, it says it cannot connect securely and it just keep on loading.

    • Hi Pops!

      My father-in-law also uses Bluehost and they changed the name of his server from box123 to box789 (not the actual server names but you know what I mean). That caused the credentials not to work anymore and the security warning. So I’d recommend to log into the Bluehost webmail interface and verify what the proper server name should be!


  11. Hi Michael, I just update my OS to Big Sur. When I went to open my email, the account was stating it was read only. None of my existing email accounts were there. When I try to add them back in, I can’t. It just gets stuck on the page where you pick which apps you want to bring in. (contacts, mail, etc). Any assistance/advise would be appreciated.


  12. Hey Michael,

    after updating to Big Sur, Mail is completely empty and wants me to add an account. Any idea how i can get back my three accounts with multiple folders? I can see all my Mailboxes in the “V8”-folder in the Library-folder, but have no clue how to get Mail to use these accounts and mailboxes. Thank you!

    • Hi Christian!

      If your mail accounts are of type IMAP or Exchange, adding the accounts back should restore the folder structure. If you have POP3 account, that won’t be the case.

      Have you tried rebooting? Big Sur normally upgrades its mail database and I guess something went wrong with that step. I haven’t experienced that issue yet, so I don’t have a good solution for you.

      But whatever you do, make sure to create a backup of your Library/Mail folder.


      • Thanks Michael, it worked. I added the accounts and everything was back. Of course I had backups before updating. Rebooting didn’t do a thing.

        Thank you again for your quick answer.

  13. Michael, I do hope you can help me. My Apple Mail preferences are set to “Manually” for downloading emails.

    This has worked as intended on my old Mac, running Yosemite. However, all my Gmail accounts were POP.

    On my brand new Mac, running Big Sur, Mail automatically turned the mail accounts to IMAP. This is fine.

    But the Mail.app ignores my setting and downloads all available emails from these IMAP accounts (and a test POP account I made) automatically.

    I’ve rebooted, set to download every hour but it still downloads automatically. I’ve shut down Mail and re-opened – no change.

    I worked for some hours with a support specialist but after testing things (including testing the situation on another user account, same thing happens) it seemed to be a problem on Googles end. But speaking to them, they were clear it’s not, and when I then set up an IMAP test gmail on my old Mac, I realised that no, it’s Apple Mail, and others seem to be having the same problem from some years ago on older operating systems.

    All help much appreciated.

  14. Hope you can help Michael, because nobody else can! A couple of months back I “updated” to Catalina but quickly realized it had robbed me of critical functionality, especially in the Preview app. So I proceeded to reinstall Mojave 10.14.6 which was largely successful. Trouble is since that day my mail app is totally unsearchable. Type in ANYTHING and all there is below is a vast black space. I have tried deleting all the envelope index files in the V6 mail data folder but same result every time. I have also forced the entire drive to re-index in spotlight but NOTHING seems to be able to give me this key functionality back. Please help!

    • I recently had the same problem in Big Sur and it was related to the Spotlight index. Try force-quitting all Spotlight processes and rebuilding the index to see if that helps.

      • Thanks Michael, Didn’t work for me but I doubt if I did it correctly anyway! Could you please be more specific on the steps required? You may have to type S-L-O-W-L-Y with me!

  15. Heya MK,

    After changing my password I was unable login to my hotmail in mail op on Mac OS. So I deleted the account. Upon re-adding I get the following message; ‘Check off account name or password failed’.

    The mail works just fine on iPhone and when logging in via Safari.

    Any ideas?


  16. Doesn;t fix the situation where Email works normally, but leave your computer on overnight, and the next day will not connect to the email, takes them all offline, the only fix I have found is reboot. So this eliminates, accounts login, credentials etc, and seems to aim at the email client problem, which is hard to beleive with Apple QA, but alas I suffer.

  17. I am still using Mojave OS, and my Apple Mail account (synchronised with an Exchange server) seems to have been scrambled when my provider upgraded my internet service. This resulted in recurrent crashes and various error messages (“The message could not be saved” and “MCMailError Domain error 30”). After trying various approaches, I simply unchecked the Mail account in System Preferences Accounts and went through the laborious process of waiting until the entire (quite large) account reloaded. Once completed, the instability was gone and the frequency of error messages was much reduced but not they are not completely gone. However, I have a remaining problem: my Drafts and Trash folders are not synchronising with the server. For each mail box folder, I’ve tried both “Synchronise” and “Rebuild”, but nothing happens. Both folders are fully populated when I log into the account using a web browser. I would appreciate any advice you might be able to offer. Thank you, Jon

    • Hey Jon,

      I would close Mail.app, remove the offending account in System Preferences and then open Finder, navigate to ~/Library/Mail/ and delete the V8 folder (make a backup before, just in case).

      Then add the account back.

      • Apologies for the delay in my reply, Michael, but I have been distracted by other issues. I went to the folder you indicated but there is no V8 folder; only a V2 and V6 folder. Should I delete both of these? There is also a file called Persistenceinfo.plist

        Mail continues to crash and completely lost the messages I had opened to manage later, so I really must do something radical to fix or abandon Apple Mail altogether.

        Thanks for your help! Jon

        • Hey Jon,

          depending on the version of macOS you have, V6 might be the most current one. So I’d move both folders (while Mail.app isn’t running) to your desktop and then restart Mail.

      • By the way, I found this recommendation on an Apple Support thread, which seems to involve deleting a lot of files. i would value your opinion on this approach:
        Quit Mail.

        In the Finder, hold down the option key and select

        Go ▹ Library

        from the menu bar. Move the following items from the folder that opens to the Trash (some may not exist):
        Saved Application State/com.apple.mail.savedState
        Application Support/AddressBook/MailRecents-v4.abcdmr
        Note: you are not moving the Mail application. You’re moving a folder named “Mail.”

        • You can do all that — I’d just create a copy of each file, especially the Mail folder. By doing so, you’ll delete all mail settings, the email auto complete history (when typing an email address), and all locally downloaded mail. The latter isn’t an issue if all of your mail is stored on Gmail or an Exchange/IMAP server. It will result in a loss of emails if you used POP3 to download your emails.

          • Thank you, Michael.

            Well, I removed the account, deleted all the files, and then reconnected Mail to the MS Exchange server. My account is huge (i.e. too big, so must archive some it soon), so the rebuilding of the account took more than two days(!). Along the way, I had to quit and restart Mail a few times, as it appeared to get stuck now and again. That said, I am now back up and running, although a few emails in my intray clearly (still) have the wrong date and time – not sure what that’s about.

            Anyway, thanks for your advice. I can vouch for the fact that (at least for me) it worked!

            Best, Jon

  18. Hi,
    I have a real issue with mail/Gmail.
    Deleted emails keep reappearing on my macbook. I’ve rebuilt mailboxes, deleted and reinstalled accounts, and it’s getting very frustrating. The Gmail settings appear to show I’m using both POP and IMAP – could this be the cause? And if I disable POP will I lose emails already on the macbook? Finally, can I delete the All Mail box? I have a single email account and it seems pointless to have everything twice. Thanks!

    • Hi Geoff,

      You might have both IMAP and POP enabled but what matters is the connection type in Mail.app on your MacBook. I assume that’s IMAP but you should double-check. Also make sure the settings in both Gmail and Mail.app are to move deleted messages to the trash rather than to archive them.

      Using POP is not advisable and you can’t delete the All Inboxes (in Mail.app) as far as I know. Plus, it’s just a virtual container, not a real mailbox.

  19. When I am offline I cannot compose an email message in Mac Mail, it does not recognise email addresses and is really slow to type. Any ideas? I cannot see anyone else with this problem! If I turn accounts offline first before I have no internet this seems to help but not always going to be able to do this.

    • Hi Joanne,

      I never heard about or had this issue. I’d create a second user account on your Mac and see if the issue happens there as well. You can also delete all of your Mail accounts (make sure you have a backup if your mails aren’t stored in the cloud) and re-add them.


  20. I keep getting a pop up and when I hit OK ti just keeps popping back up and it prevents me from using apple mail.

  21. I am recently facing issues on one of the staff at the office when setting up his O365 eMail on his Mac. I delete and add his eMail profile but it says downloading x/xxx and gets stuck there (x is a randomly number each time I delete & add his account). I’m frustrated over here.

  22. I spent most of the last day or so trying to change my email from a POP3 set up to an IMAP setup… I was one of those unlucky Verizon folks that had to migrate to AOL a while back… Also, I was using Outlook so that added another monkey wrench as I tried to get my email sorted out! Just when I was about to give up hope (and had solved 95% of my problem by trial and error) I found this article. THANK YOU!!! I followed your steps and with one minor tweak (changing auth to password), all is good in my email world!
    … for now, at least! LOL

  23. Many thanks indeed, Michael! SMTP now working on iMac. Still no joy on ancient laptop (Mail v6.6, OS 10.8.5), which also suddenly forgot how to send, but I’m content to use webmail, not wanting to embarrass this old beast…
    Best wishes

  24. Michael, thanks for your advice. I have a slightly different problem. I have a Mac, running Catalina, and an iPad mini 4 running 13.1.3 and an iPhone XR running 13.1.3. I access Mail on all 3 devices. But if my Mac is turned on, mail is not delivered to the iPad and the iPhone – it is only delivered to the Mac. If my Mac is off, mail comes to the iPad and the iPhone, then, when I turn the Mac on, it is delivered to the Mac. It’s like the mail preferences on the Mac override the iPad and iPhone . Are you able to suggest a remedy? Hope you can help Kimball

  25. great info…my issue is that my email on my applemac is a pop email account, and my iphone is IMAP, therefore emails i delete from my phone wont delete from my applemac…and visa versa….I have removed the email account from applemac, and reinstated it, but no option to choose IMAP, it seems to default to a pop account….it was working fine up till a week ago when i had password issues and was instructed to remove email account
    from applemac and reinstate (i believe it was IMAP before doing this) any suggestions please! thank AC

  26. Hello and thanks for the help ahead of time, so when I pull up my email on my MacBook it keeps popping up and down with some old draft or something. Is it a virus or some steps to remove or stop it I can’t use my mail because of this. Thank you very much friend!

  27. Great help and “flipping the switch” cured the problem of not being able receive incoming emails. Many thanks

  28. I open the log from the connection doctor to see if I can diagnose why my stmp server isn’t sending my email. I see this sequence of messages repeated dozens of times in the log. I don’t see anything that suggests why the emails won’t send. Can you help?

    INITIATING CONNECTION May 04 12:41:34.742 host:smtp.mail.att.net — port:465 — socket:0x0 — thread:0x600007405300

    CONNECTED May 04 12:41:35.043 [kCFStreamSocketSecurityLevelTLSv1_2] — host:smtp.mail.att.net — port:465 — socket:0x60000452d380 — thread:0x600007405300

    READ May 04 12:41:35.043 [kCFStreamSocketSecurityLevelTLSv1_2] — host:smtp.mail.att.net — port:465 — socket:0x60000452d380 — thread:0x600007405300
    220 smtp.mail.yahoo.com ESMTP ready

    WROTE May 04 12:42:05.051 [kCFStreamSocketSecurityLevelTLSv1_2] — host:smtp.mail.att.net — port:465 — socket:0x60000452d380 — thread:0x600007405300
    EHLO []

  29. Hi Michael
    I wonder if you can help? My issue is with getting Mail to save the outgoing mail settings specifically Port 465. The Use TLS/SSL checkbox fails to save when checked. The wheel of death just keeps going round then gives up. Any ideas

  30. Looking at the Dr., my client gives up eventually, but it is using port 193 even though I have repeatedly set it to 993. I’ve quit and restarted my email client to try to clear any cache. High Sierra OS – mac client.

    Thank you for any help.

  31. More info…at the bottom of my inbox list of emails, it says “Updated Thursday, Account Error: Yahoo” and “Details” (in blue) and when I press it I get “Cannot Get Mail, the connection to the server failed”. As I said in my email just previous to this one, everything is normal on my mac, and furthermore, I can use my iPhone for everything else online, and even for sending emails. It’s just receiving new emails on my iPhone that is the issue. Thank you.

  32. I can send and receive emails on my mac but as of yesterday my iPhone won’t receive new emails. I can send an email from my iPhone but new incoming emails will not show up. Why is this?

    • Hi Kat!

      The “why” is almost impossible to say, but I’d recommend you run through the steps I suggested in my article. In the worst case just remove and re-add the account.


  33. Thank you for the detailed instructions. Outlook has taken over my msn email account which I have been using for over 15 years with no problem – until now. It is telling me that someone else may be trying to use my account and when I try to verify who I am it does not accept the information. Microsoft does not give you the option to talk with a live operator – therefore, I am well and truly locked out of my email account. This has been going on for weeks now and there seems like there is no way to rectify things. I understand that if you sign in from another location it could trigger a security alert and for that I am grateful, but when you cannot fix things elecronically and you cannot get to speak with a live person – what are you to do? I am truuly exasperated with microsfot outlook – bring back my old msn…..I will enter my email address below but don’t bother writing to it because I cannot get in!!!!!

  34. Hi,
    Great info. I stupidly deleted my email account from mac mail before trying different ways to troubleshoot my email not sending and receiving and am now having trouble adding the account again. It is saying invalid account or password. I have changed my password through my hosting company and deleted the passwords in my keychain (this is what my host suggested) I’m just wondering if you have any ideas how I can re-add my email as you seem very knowledgeable on this topic? Any help would be much appreciated. :)

  35. Nice post on iphone phone. People are courageous about iphones and there is lot of hype about Apple.I bought a budget i6 but I am satisfied with the device. No glitches and no of problem in this device.


Leave a Comment