New answers tagged smtp
I would suggest that the underlying reason for the failure is that that you have appended the -S nss-config-dir="/etc/pki/nssdb/" setting after a recipient delivery address, so it is being treated as a file-based target for delivery. You can see this in your strace output provided in your answer: stat("nss-config-dir=/etc/pki/nssdb/", 0x7fff7073a310) = -1 ...
MS has a buggy TLS implementation. I was able to overcome it using Stunnel with the following config data: [office365-smtp] client = yes accept = 192.168.100.25:25 connect = my-personal-id.protection.outlook.com:25 protocol = smtp verify = 2 CAfile = ca-cert.pem checkHost = my-personal-id.protection.outlook.com
By itself, lsof -i will only list Internet information. You can add file information (or show that instead) using the -d option. For example: lsof -d txt | grep -E '/httpd.pl$' because (unless a process changes the name under which it runs) the command name will match the actual filename which was loaded. That file has to be executable, of course ...
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