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Apple Mail on macOS 10.14.4 Loses Connectivity to the Gmail SMTP Server

Recently I have noticed that the Mail app version 12.4 (3445.104.8) running on macOS Mojave version 10.14.4 (18E226) will lose connectivity to the Google Gmail SMTP server over a period of time. I am unsure as to the exact period of time that causes the connectivity loss, but would estimate that it is around 2 hours. Apple Mail reports Gmail as offline, and won't take it back online. Quitting out of Apple Mail entirely, and restarting the application will restore connectivity to Gmail. However, this is a temporary fix as the issue recurs again after another period of time. I believe that this behavior began with the update to macOS 10.14.4. Gmail previously worked without issue with Apple Mail from many years.


The issue has also been recently reported on the Google Support forums as Why does Apple Mail keep loosing connection to the Gmail SMTP server? As far as I know, there has been no satisfactory answer from either Google or Apple or the community. Many believe that it may likely be more of an Apple issue than a Google issue, as the issue appears to have started with the release of macOS 10.14.4.

iMac Pro, macOS 10.14

Posted on Apr 26, 2019 9:29 AM

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Posted on May 8, 2019 7:45 PM

SOLVED?!

I posted this on another site, and it has worked for other people.

Like all of you, I have this same problem, but I have a number of gmail accounts and one of them was working fine. I went through all the settings to find a difference, and the only thing I could find was that for the working account, I was also using the calendar. So, it would seem that if you go into System Preferences -> Internet Accounts and click on your problematic google account and activate the calendar as well, it should keep your email online. I've tried it and it also works for contacts instead of calendars, notes doesn't seem to work. I don't know why this works but, so far so good, let me know if it works for anyone else!

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15 replies
Question marked as Top-ranking reply

May 8, 2019 7:45 PM in response to -Alec-

SOLVED?!

I posted this on another site, and it has worked for other people.

Like all of you, I have this same problem, but I have a number of gmail accounts and one of them was working fine. I went through all the settings to find a difference, and the only thing I could find was that for the working account, I was also using the calendar. So, it would seem that if you go into System Preferences -> Internet Accounts and click on your problematic google account and activate the calendar as well, it should keep your email online. I've tried it and it also works for contacts instead of calendars, notes doesn't seem to work. I don't know why this works but, so far so good, let me know if it works for anyone else!

May 15, 2019 3:23 PM in response to Wim_Apple

No, it should exist for all Mac's that run macOS; however, perhaps Apple is rolling it by selected countries or in phases somehow. That I would not know. You should be able to find the update either by clicking on  > About this Mac > Software Update... or via System Preferences > Software Update. Either method should take you to the following dialog box where any new update would appear...


Apr 28, 2019 11:50 PM in response to -Alec-

I do have the exact seam issue since update to 10.14.4

Tried to disconnect then reconnect every thing with iCloud, but the problem remains.

Just wrote this reply to make sure I'll be informed when a solution pop's up

I should add that this gmail issue doesn't seem to exist with the iPhone, only with may macbook.


Thanks Alec for having asked :)

May 4, 2019 10:21 AM in response to -Alec-

I got the same problem and phoned Apple Care, who solved the problem, which was a corrupted password file.

(Do not ask me why the server connection sometimes worked and sometimes failed)

This happens easily when converting to MacOS 14+, where the password file has a different format and so needs to be translated.

It might have been corrupted by some malware on my computer. So the following steps were taken to solve the problem:


1) perform the free download of Malwarebytes from https://www.malwarebytes.com/mac/

2) scan the computer

3) remove the malware with the program, if anything is found

4) empty the quarantaine folder, if anything was found. You can deinstall the program with the option on "help". Else you are asked to pay after one month free trial.

5) Open the program to manage the passwords (under programs/serviceprograms/ or search for "Schlüsselbundverwaltung.app" with the magnifier on the top right of the screen on a German language computer)

6) NOW YOU HAVE TO REMOVE ALL PASSWORDS WITH THE PROGRAM. BE SURE YOU KNOW ALL YOUR PASSWORDS. If you are not sure, display them with the program and write them down.

This works only if the file is not completely corrupted. Fortunately I had an older MAC with an older system, where I could display most of the passwords. Note: one cannot copy this old file into the new file because of the different format.

7) Setup all Email accounts from scratch.

8) Reenter all passwords if the computer asks for one, like by login to websites.


Then everything works fine again.


Good luck.


Cheers,


Wim

May 15, 2019 7:52 AM in response to -Alec-

It looks like Apple may have fixed the issue in macOS 10.14.5 (18F132).


I hadn't yet followed the "activate the calendar as well" trick recommended by jacqlou as I don't want my Google Calendar integrated on this Mac. I have just been clicking the little bolt icon next to the Gmail account to bring it back online. (Strangely, the Mailbox > Take All Accounts Online menu option would not work for me, but the little icon trick did... who knows why?)


In any event, I was still encountering the issue until last night when I upgraded from 10.14.4 to 10.14.5. This morning when I woke my iMac, all of my email accounts were still connected. I believe there was likely a bug fix for this issue in the patch.

Apple Mail on macOS 10.14.4 Loses Connectivity to the Gmail SMTP Server

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