Thanks Michael – I’m new at “inspecting on the wire” but here’s what I’ve found.
MailerSend requires TLS and port 587. So:
- I created an alternate app.yml to send to a free mailtrap.io account on port 2525
- set
DISCOURSE_SMTP_ENABLE_START_TLS = false - applied the change with:
cd /var/discourse
./launcher destroy app
./launcher start app
- set up Wireshark to monitor remote traffic via tcpdump
The email content packets in Wireshark and the unencrypted emails received at Mailtrap do not, so far, have any missing space characters. Specific test digests run back-to-back with each config have missing spaces with my original config and not with the mailtrap version. Could this indicate that the problem is introduced with the TLS encryption?
EDIT: It occurred to me that I didn’t fully utilize the Mailtrap testing setup. I’ve since run several encrypted preview summaries to Mailtrap — on port 587 with TLS enabled — and have not seen any dropped space characters. I’m now thinking that despite MailerSend telling me the issues were present in the received requests, it maaaay be happening on their end after all? Not sure what to have them look for, but I plan to run these findings by them.