Boylan, Ross via Exim-users <exim-users@exim.org> (Di 09 Jul 2019 01:52:23 CEST):
> 14:55:44 SMTP>> AUTH LOGIN > 14:55:44 cmd buf flush 12 bytes > 14:55:44 read response data: size=18 > 14:55:44 SMTP<< 334 [gibberish] > 14:55:44 SMTP>> **************************** > 14:55:44 cmd buf flush 30 bytes > 14:55:44 read response data: size=18 > 14:55:44 SMTP<< 334 [different gibberish] > 14:55:44 SMTP>> ************************ The gibberish is probably something like "Username" and "Password", but base64 encoded. Try `openssl base64 -d <<<GIBBERISH` > 14:55:44 cmd buf flush 26 bytes > 14:55:50 read response data: size=81 > 14:55:50 SMTP<< 535 5.7.3 Authentication unsuccessful > [BYAPR04CA0001.namprd04.prod.outlook.com] > 14:55:50 login authenticator yielded 2 > 14:55:50 LOG: MAIN > 14:55:50 login authenticator failed H=SJC-efz.ms-acdc.office.com > [52.96.3.178] 535 5.7.3 Authentication unsuccessful > [BYAPR04CA0001.namprd04.prod.outlook.com] > 14:55:50 SMTP>> MAIL FROM:<ross.boy...@ucsf.edu> SIZE=1623 Hm. Why does your side continue sending the data, even the authentication didn't succeed? If you know that outlook.com doesn't accept unauthenticated connections, you can use hosts_require_auth in the transport talking to outlook.com I'd try using swaks swaks -tls -a login -au $username -ap $password -f $sender -t $recipient \ -s 52.96.3.178 \ -q auth or similar (I didn't test the command line yet). This should reveal if you can authenticate with them at all. And then, as step 2, use this auth data in your Exim configuration. Best regards from Dresden/Germany Viele Grüße aus Dresden Heiko Schlittermann -- SCHLITTERMANN.de ---------------------------- internet & unix support - Heiko Schlittermann, Dipl.-Ing. (TU) - {fon,fax}: +49.351.802998{1,3} - gnupg encrypted messages are welcome --------------- key ID: F69376CE - ! key id 7CBF764A and 972EAC9F are revoked since 2015-01 ------------ -
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