Cannot Send E-mail Notification

[Christopher Stout]

A stable connection to the server could not be established.

This is the error in the GUI that I get each time I try to test sending an e-mail. This iMac has been e-mailing properly for about 8 months now and just stopped this week. Now, all I get is this error. I plugged in the same smtp details in a VM on the same computer and it sent the test e-mail fine.

That info alone seems to put the blame on my iMac, but here's why I'm reaching out. I'm trying to find out what the error is in regard to specifically so I can better troubleshoot. The log gives me very little to work with and is excerpted below. I've done a full uninstall of AutoPkgr via the uninstall option as well as manually deleting every file listed on the uninstall info page. I've even disabled iCloud Keychain and deleted all local files in ~/Library/Keychains. I have no idea what remains that would continually prevent successful e-mail from being sent.

Any ideas are greatly appreciated.

Jul 25 18:12:13 iMac syslogd[49]: ASL Sender Statistics

Jul 25 18:12:15 iMac com.lindegroup.AutoPkgr.helper[1139]: Sending keychain key to AutoPkgr.

Jul 25 18:12:37 --- last message repeated 1 time ---

Jul 25 18:12:37 Stout iMac com.apple.xpc.launchd[1] (com.apple.imfoundation.IMRemoteURLConnectionAgent): Unknown key for integer: _DirtyJetsamMemoryLimit

Jul 25 18:12:37 --- last message repeated 2 times ---

[Christopher Stout]

I'm not sure what the problem is but I switched to a different smtp server and it works. It's behaving like the Google smtp server was blocking my iMac, but if that's the case I'm not sure how the same account set up on the same computer (within a VM) would succeed. MAC address blocking, maybe? Not sure. All good now using a non-Google smtp server.