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I recently upgraded to Mojave from Mountain Lion on a Mac Mini Late 2011. After upgrade, the Mail app would not connect to the mail server any more. I followed a few online articles and dragged the /User/Library/Containers/com.mail.app/ folder to the desktop and restarted but it would not connect. So, I deleted the mailbox and tried to install it again, but, no luck.

Finally, I created a new user account in the OS and successfully set up the mail accounts there. However, I don't want to migrate the whole account over since there are many settings, scripts, and network connections for that user in apps such as Adobe suite, etc.

Is there any other steps I can take to fix the mail app within the initial user instead of trying to migrate the user? Is deleting the mail app and then reinstalling Mojave from the startup going likely to fix the issue or is there any other plist files or directories I can remove to allow macOS to regenerate that would be causing errors in one user account but not the other? I saw that some file structure within the com.mail.app were different than a fresh Mojave install.

  • Lion to Mojave in one jump is really not recommended. You should at minimum go via El Capitan; & Sierra to be safe. – Tetsujin Dec 7 '18 at 19:41
  • Yikes. Where can I find out about these recommendations beforehand? The roll-over is done now, and only one issue among 20+ workstations. It is this issue of mail not working in only one user account. The other use account it works. I could migrate everything over to the other user, but for networking and app specific configurations, I would just rather get Mail working in the user. – rippledj Dec 7 '18 at 19:43
  • tbh, I don't know where this info originates [& it's not a scenario I have ever personally had to reconcile] but I'm surprised the OS/App Store would even offer Mojave to a Lion machine. It ought to offer the El Cap 'get out of jail free' link instead. Maybe see apple.stackexchange.com/questions/309399/… for some background, though it doesn't actually cover this specific scenario. – Tetsujin Dec 7 '18 at 19:47
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    One place to look in Mail prefs>accounts>server settings [& also the equivalent inside the SMTP settings] is to disable the 'automatically manage...' structure - which was 'known bad' for several types of connection, including Exchange. I haven't tested it in a long time to see whether it's fixed, & have left mine off since about Mavericks. – Tetsujin Dec 7 '18 at 19:52
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    tbh, it's the kind of leap, 6 or 7 major OS versions with no safety net, I would avoid if at all possible. It's like hoping you can get from Win2k to Win10 in one hop. If you have a backup/clone from before & can't get this fixed easily, I'd go for the incremental approach instead & see how it goes. It is generally possible, without major hiccup, to progress all the way from Panther to Mojave. I've done it [not in a week,. it took many years], but I have direct generational updates that do really stretch back that far. My current main Mac has direct line-of-sight back to 2001. – Tetsujin Dec 7 '18 at 19:58

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