Hmm this is interesting that you no longer have a ticketing system.
Outlook is throwing a 0x800CCC67 error on being unable to establish an encrypted connection to the outgoing smtp server.
Doing a check on https://www.checktls.com/ shows also confirms that the issue is not client-side related - even though TLS is an option on the server, the certificate is not valid.
This seems like it was an issue back in August 2019 too - but the Slack invite link there is dead, so I can’t post there