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Hello.
What about doing a packet capture using something like "tcpdump"?
Regarding the "tcpdump" command, this answer may be helpful.
https://repost.aws/questions/QUlQYKoGVNQkuKY_bdyU5DNg/ses-update-tls-connections-to-1-2-to-maintain-aws-connectivity#ANuiqMgNVxTLqHA90aDR7SWw
I don't think it's very likely, but could it be blocked by the OS's firewall?
Using Wireshark, I see there is a difference in the network trace between a working/non-working environment. See my Edits with screen capture in my original post.
Side note, the emails works on most devices in my inventory but does not work on 2 specific computers.