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Mac mail connects and then disconnects with no discernable pattern. Connection doctor just spins and says it can't connect to the server. BUT... if I am connected to a VPN then everything works fine.

New Macbook Pro, 10.14.6 osx.

I have tried:

Deleting the network related plists in Library/Preferences/SystemConfiguration/

com.apple.airport.preferences.plist
com.apple.network.eapolclient.configuration.plist
com.apple.wifi.message-tracer.plist 
NetworkInterfaces.plist
preferences.plist
  • I have updated the 10.14.6
  • I have deleted and reinstalled all of the email accounts
  • I have disabled all monitoring, scanning and filtering
  • I have rebuilt the mail accounts
  • I have tested with numerous VPNs and they all keep the connection alive or correct the error if activated after a fault.

without VPN

The connection will work for a varying amount of time but typically no more than 15 minutes after a reboot. When it works, everything works great then it simply stops working. Typically the Gmail account will fail first, then the iCloud. The Exchange account never fails to connect. I had a POP account that would also fail but I have removed it to troubleshoot.

Everything works if I boot into safe mode.

QUESTION: What logs can I provide to help troubleshoot?

  • Could you clarify a bit more on this. For Gmail and icloud accounts only, can you try without VPN. I think your POP account is giving issue ? – Udhy Sep 30 '19 at 13:58
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    Welcome to Ask Different. Please see How to Ask for important info on asking questions here. What do you mean when you say you did "all the normal stuff"? Can you edit your question to list what you've already done? – fsb Sep 30 '19 at 14:17
  • Is there a firewall or screening service between you and the internet which you might be bypassing using the VPN? You can also add a screenshot of the Connection Doctor after redaction. – ankii Sep 30 '19 at 16:52
  • @Udhy - I have removed all filtering, scanning and VPNs on my Mac and router and my ISP (Virgin Media). Then rebooted, deleted all the .plist network files and rebooted and reconnected to the network. Then I launched mail.app and it works for some varying amount of time up to 15 minutes then it fails - typically starting with the Gmail account then the iCloud account but the Exchange account never fails. – Todd Facemire Oct 1 '19 at 11:01
  • 1 could you simply delete the comment you tagged me in? I read it and .. you know.. it's copied. Leave the one with Udhy 2 any chances you know about some third party kernel extension, antivirus/anti-malware etc installed ? 3 you can list all using kextstat | grep -v com.apple. – ankii Oct 1 '19 at 13:20

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