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I am seeking the fix for Apple mail not sending after latest OS updates;

I am seeking the fix for Apple mail not sending after latest OS updates; for the last three days I have not been able to use Apple Mail... it receives mail but does not send. I have multiple email accounts set up apple, gmail and my local ISP... all were working fine before 10.14.4.


I have with Apple Support's help/suggestions: booted in safe mode (still has the problem), reset the NVRAM, and reinstall the OS. None of these things have restored Apple mail to full functionality.


I try to set server settings but Apple mail will not save the new information.


Does anyone have the solution?


I'm planning to call Apple Support tomorrow but thought perhaps there is knowledge out there that will get me up and running.


Thanks!


MacBook Pro 15", macOS 10.14

Posted on Mar 29, 2019 10:11 PM

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Question marked as Best answer

When I resumed working the issue today I had the same issues even though I had disabled iCloud associations thinking that would help with saving settings. Still no improvement... so I called Apple Support to continue working the problem. Shaundra had me delete the accounts in Internet Accounts and try to reenter them. Still they would not verify... when I told Shaundra that I had done an Adobe Acrobat update and inadvertently/unintentionally downloaded two third party softwares she then suggested I run Malwarebytes on my machine. She walked me through the download and scans, two till I got an all clear from the program, and then we returned to add my email accounts... Violá!!! Problem solved!!!


Thanks for all the responses; ultimately the problem was adware that was disrupting my email account activity. And yes, I have changed credentials on the accounts.


Thank you Apple for providing caring customer support!!!

Posted on Mar 30, 2019 4:27 PM

1 reply
Question marked as Helpful

Mar 30, 2019 12:58 AM in response to Christina NM

There have been a number of posts following this latest update and issues with Mail but mostly connected with Gmail accounts on the Authentication side, but strangely enough I also had a problem with the SMTP side of the two mail accounts I use.


After the update I noticed in Mail's Connection Doctor that for both iCloud and my third party ISP account the SMTP Server was not showing a successful connection and login to the server, for it to happen on one ok, but both seemed strange. The SMTP server is responsible for sending by the way.


The error report within the Mail App itself (when you see the triangle next to the account) reported something like a connection could not be made because one already existed (can't remember exact wording). This was strange because I hadn't used any of my iDevices so as far as I could tell it was just the iMac trying to establish a link.


That made me suspect that somehow the two accounts on the SMTP side were getting mixed up and causing the conflict which I then tried to prove by turning off iCloud, when this was done my third party ISP account was functioning again, but reenabling iCloud caused the issue to return.


I ended up turning off iCloud Mail altogether under the Account Information tab of Mail Preferences and then using the "-" button to delete the ISP account after exporting all messages (I still use a POP account so content is downloaded on to the iMac and not kept on server). After closing Mail and rebooting I added back my ISP account (had some configuring of port number and SSL by hand though) and then reenabled iCloud.


That seemed to fix the issue.


Had one strange thing though, when reenabling iCloud (ticking the box under Account Information) I noticed under the Server Settings tab it said "None", I then had to select iCloud under that dropbox, but it didn't appear to "stick" so I had to do this several time switching between the account information views before it finally stayed selected.


I hope some of the above gives you some further ideas (and sorry for using "strange" so many times), I appreciate that having just two accounts made this a little easier for me but may be you could just concentrate on getting the most important one working first (remove all others after backing up messages) and if successful add the others back one at a time.

7 replies

Mar 29, 2019 10:44 PM in response to Christina NM

Do you have a Time Machine or CCC backup of your startup drive from before the problem began occurring?


You state that you reinstalled Mojave, but did you do a clean install, or did you install on top of your current system? If the latter, then this might explain why the problem still exists.


On the other hand, if you do a clean install, then it should totally wipe out the problem, being as you are starting from scratch.


Are you receiving any kind of on-screen error messages when you attempt to send mail, such as in the lower section of the mailboxes column?


Question marked as Helpful

Mar 30, 2019 12:58 AM in response to Christina NM

There have been a number of posts following this latest update and issues with Mail but mostly connected with Gmail accounts on the Authentication side, but strangely enough I also had a problem with the SMTP side of the two mail accounts I use.


After the update I noticed in Mail's Connection Doctor that for both iCloud and my third party ISP account the SMTP Server was not showing a successful connection and login to the server, for it to happen on one ok, but both seemed strange. The SMTP server is responsible for sending by the way.


The error report within the Mail App itself (when you see the triangle next to the account) reported something like a connection could not be made because one already existed (can't remember exact wording). This was strange because I hadn't used any of my iDevices so as far as I could tell it was just the iMac trying to establish a link.


That made me suspect that somehow the two accounts on the SMTP side were getting mixed up and causing the conflict which I then tried to prove by turning off iCloud, when this was done my third party ISP account was functioning again, but reenabling iCloud caused the issue to return.


I ended up turning off iCloud Mail altogether under the Account Information tab of Mail Preferences and then using the "-" button to delete the ISP account after exporting all messages (I still use a POP account so content is downloaded on to the iMac and not kept on server). After closing Mail and rebooting I added back my ISP account (had some configuring of port number and SSL by hand though) and then reenabled iCloud.


That seemed to fix the issue.


Had one strange thing though, when reenabling iCloud (ticking the box under Account Information) I noticed under the Server Settings tab it said "None", I then had to select iCloud under that dropbox, but it didn't appear to "stick" so I had to do this several time switching between the account information views before it finally stayed selected.


I hope some of the above gives you some further ideas (and sorry for using "strange" so many times), I appreciate that having just two accounts made this a little easier for me but may be you could just concentrate on getting the most important one working first (remove all others after backing up messages) and if successful add the others back one at a time.

Mar 30, 2019 4:25 PM in response to SiHancox

This is what I was thinking as I went to bed last night... When I resumed working the issue today I had the same issues even though I had disabled iCloud associations thinking that would help with saving settings. Still no improvement... so I called Apple Support to continue working the problem. Shaundra had me delete the accounts in Internet Accounts and try to reenter them. Still they would not verify... when I told Shaundra that I had done an Adobe Acrobat update and inadvertently/unintentionally downloaded two third party softwares she then suggested I run Malwarebytes on my machine. She walked me through the download and scans, two till I got an all clear from the program, and then we returned to add my email accounts... Violá!!! Problem solved!!!


Thanks for your feedback; it affirmed my thinking. But ultimately the problem was adware that was disrupting my email account activity. And yes, I have changed credentials on the accounts.

Question marked as Best answer

Mar 30, 2019 4:27 PM in response to Christina NM

When I resumed working the issue today I had the same issues even though I had disabled iCloud associations thinking that would help with saving settings. Still no improvement... so I called Apple Support to continue working the problem. Shaundra had me delete the accounts in Internet Accounts and try to reenter them. Still they would not verify... when I told Shaundra that I had done an Adobe Acrobat update and inadvertently/unintentionally downloaded two third party softwares she then suggested I run Malwarebytes on my machine. She walked me through the download and scans, two till I got an all clear from the program, and then we returned to add my email accounts... Violá!!! Problem solved!!!


Thanks for all the responses; ultimately the problem was adware that was disrupting my email account activity. And yes, I have changed credentials on the accounts.


Thank you Apple for providing caring customer support!!!

Mar 30, 2019 4:30 PM in response to WordWeaver777

The install was done as Apple Support techs directed so I assume it was done properly. All kinds of errors and that let me to all the actions taken.


When I resumed working the issue today I had the same issues even though I had disabled iCloud associations thinking that would help with saving settings. Still no improvement... so I called Apple Support to continue working the problem. Shaundra had me delete the accounts in Internet Accounts and try to reenter them. Still they would not verify... when I told Shaundra that I had done an Adobe Acrobat update and inadvertently/unintentionally downloaded two third party softwares she then suggested I run Malwarebytes on my machine. She walked me through the download and scans, two till I got an all clear from the program, and then we returned to add my email accounts... Violá!!! Problem solved!!!


Thanks for your feedback; nothing new for me to consider but I appreciate your concern. Ultimately the problem was adware that was disrupting my email account activity. And yes, I have changed credentials on the accounts.

I am seeking the fix for Apple mail not sending after latest OS updates;

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