Google Mail SMTP Account Failure & Apple Mail

Hello,
Every once in a while the SMTP login for my gmail accounts fail in Mail. I'll get an error message like this:
"Trying to log in to this SMTP account failed. Verify that the username and password are correct."
I use 2 factor authentication and app specific passwords so I'm not sure if this is the issue. In any case, it is a pain to have to go and reset all the passwords every time this happens. This doesn't seem to be an issue with my iPad just Mail on my mac mini.
Does anyone know what causes this? and how I can prvent it from happening?
Best regards
Jackie

If you have a Gmail account and you've activated 2-step verification, you need to generate a new "application-specific password" in your Google account and enter it in place of your old password in the Keychain Access application.

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    1 libobjc.A.dylib 0x00007fff83b2357c objc_addExceptionHandler + 1026
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    18 com.apple.AppKit 0x00007fff82b4b1bf -[NSView _recursiveDisplayRectIfNeededIgnoringOpacity:isVisibleRect:rectIsVisibleRectFor View:topView:] + 4555
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    20 com.apple.AppKit 0x00007fff82b4b1bf -[NSView _recursiveDisplayRectIfNeededIgnoringOpacity:isVisibleRect:rectIsVisibleRectFor View:topView:] + 4555
    21 com.apple.AppKit 0x00007fff82b4b1bf -[NSView _recursiveDisplayRectIfNeededIgnoringOpacity:isVisibleRect:rectIsVisibleRectFor View:topView:] + 4555
    22 com.apple.AppKit 0x00007fff82b4b1bf -[NSView _recursiveDisplayRectIfNeededIgnoringOpacity:isVisibleRect:rectIsVisibleRectFor View:topView:] + 4555
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    22 libSystem.B.dylib 0x00007fff85c39bb8 pthreadwqthread + 353
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