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I now have the *SYSTEM cert store trusting everything built in, and the two certs I got from Google.

Looking at DCM in a different browser, I was able to figure out how to remove the cert associations I'd created earlier, with my local-CA-signed cert. But it didn't make any difference. The results don't change.

On the Midrange side, I still typically get:

ID: 004B5A-Q60-002393000000298C20 Time Received: 10/25/22 12:04:00.922
Recipient:


E-mail LOG:
10/25/22 12:04:00 0029 Recipient jamesl@xxxxxxxxxxxxxxxxx transfered to serve
10/25/22 12:04:00 0029 r directly
10/25/22 12:04:00 0029 Recipient jhhl@xxxxxxxxx transfered to server directly
10/25/22 12:04:02 003B Marking jamesl@xxxxxxxxxxxxxxxxx as WRK
10/25/22 12:04:02 003B Marking jhhl@xxxxxxxxx as WRK
10/25/22 12:04:02 003B Connected to Server SMTP-RELAY.GMAIL.COM(142.251.12.28
10/25/22 12:04:02 003B ):587
10/25/22 12:04:02 0040 Relay already in processing, skip it
10/25/22 12:04:04 003F Marking jamesl@xxxxxxxxxxxxxxxxx as NDL
10/25/22 12:04:04 003F Marking jhhl@xxxxxxxxx as NDL

and in the Google logs, it shows up as:

Subject: null
Sender: info@xxxxxxxxxxxx
Recipient: 0 recipients
Date: Oct 25, 2022 9:07:59 AM
Message ID: <635...SMTPIN_ADDED_REJECT_SESSION_161310@xxxxxxxxxxxx>
Message Size: 0 B
Attachments: 0
Direction: Sent
Status: 0/0 Delivered

--
JHHL

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