On Mon, Jul 08, 2019 at 11:52:23PM +0000, Boylan, Ross via Exim-users wrote:
> My immediate question is whether the transcript at the bottom gives any
> clues about the problem.  In particular, does the absence of a user account
> from the transcript mean it is not attempting to login as me?

 No, Exim hides your real authentication data when running with -d.

> 14:55:44 scanning authentication mechanisms
> 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>> ************************

 Usually server response (which was wiped out by you) contain
 "334 VXNlcm5hbWU6", where 2nd token is base64-encoded "Username:" word,
 and "334 UGFzc3dvcmQ6", where 2nd token is "Password:".
 Run base64 utility to decode.

> 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]

 The server replies that this login/password pair is incorrect.
 You have to check your credentials.

> 14:55:50   SMTP>> MAIL FROM:<[email protected]> SIZE=1623
> 14:55:50   SMTP>> RCPT TO:<[email protected]>
...
> 14:55:55   SMTP<< 530 5.7.57 SMTP; Client was not authenticated to send 
> anonymous mail during MAIL FROM [BYAPR04CA0001.namprd04.prod.outlook.com]

 Exim4 tried to send mail without authentication, buf server rejects it.
-- 
 Eugene Berdnikov

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