When the SMTP service is configured to use a relay server, QWK/FTN addressed messages should still use internalized routing, not the smtp relay/gateway.
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Discovered when hitting "Reply" in Thunderbird on NNTP messages.... not meaning to, but would be nice if it worked... Why Thunderbird puts "Replay" before "Followup" (reply in group) is beyond me.
"Configured to use relay server" impacts the behavior of the Mail Server's "Sendmail Thread" only, not the SMTP server (the service that receive SMTP-submitted email). When the SMTP server receives messages addressed to FTN or QWKnet destinations, they're stored in the mail base accordingly and the Mail Server's Sendmail Thread will never see or attempt to send such messages. The "use relay server" setting does not play a role with such messages.
Not really.. it was happening when I'd hit "reply" (opposed to "follow-up") to a message in NNTP in Thunderbird... It would email the DoveNet QWK address that NNTP would show... but I'd get a bounce message back from sendgrid saying it didn't understand the address...
I don't have a recent example, and Thunderbird no longer works with Synchronet's NNTP, so I'd have trouble to recreate it at the moment.
I wouldn't expect "sendgrid" to recognize a QWKnet or FTN address. If your Thunderbird mailer was configured to use a Synchronet mail server for email, then it would (and does) work.