One addition: The swaks command line you'll need to test properly will be something like this:
swaks -tls -t tar...@example.com --auth-user joea --server mail.example.com:587 On 2022-01-14 at 12:33:18 UTC-0500 (Fri, 14 Jan 2022 12:33:18 -0500) Bill Cole <postfixlists-070...@billmail.scconsult.com> is rumored to have said: > On 2022-01-14 at 12:10:23 UTC-0500 (Fri, 14 Jan 2022 12:10:23 -0500) > Joe Acquisto-j4 <j...@j4computers.com> > is rumored to have said: > [...] >> I guess this is going a bit astray, for some viewers anyway, but after >> repeated authentication failures, resorted to (or availed myself of) >> SWAKS and still get authentication failures. I did set swaks to >> echo the credentials in plaintext, to the screen and know they >> are correct. I am unsure why they are "broken up" with "->" and >> <-" and wonder if that should provide a clue? > > Lines with '<-' are coming from the server (Postfix,) '->' lines are sent by > the client (SWAKS.) > >> Below is what is echoed to the screen. >> ~ # swaks >> === Trying mail.somehost.com:587... >> === Connected to mail.somehost.com. >> <- 220 mail.somehost.com ESMTP Postfix >> -> EHLO auxilary >> <- 250-forwardx.somehost.com >> <- 250-PIPELINING >> <- 250-SIZE 56789012 >> <- 250-VRFY >> <- 250-ETRN >> <- 250-STARTTLS >> <- 250-AUTH PLAIN LOGIN >> <- 250-AUTH=PLAIN LOGIN >> <- 250-ENHANCEDSTATUSCODES >> <- 250-8BITMIME >> <- 250 DSN >> -> AUTH LOGIN >> <- 334 bla- >> -> blah-user >> <- 334 bla >> -> blah-password >> <** 535 5.7.8 Error: authentication failed: UGFzc3dvcmQ6 >> *** No authentication type succeeded >> -> QUIT >> <- 221 2.0.0 Bye >> === Connection closed with remote host. > > I do not see a "STARTTLS" there, so my guess would be that the server is > configured to only allow authentication with encryption active. That would be > entirely normal, as the server is only offering plaintext AUTH mechanisms > (PLAIN and LOGIN) which should only be done over encrypted channels. > > > > > -- > Bill Cole > b...@scconsult.com or billc...@apache.org > (AKA @grumpybozo and many *@billmail.scconsult.com addresses) > Not Currently Available For Hire -- Bill Cole b...@scconsult.com or billc...@apache.org (AKA @grumpybozo and many *@billmail.scconsult.com addresses) Not Currently Available For Hire
