[MlMt] Office365 SMTP / OAuth2

[John Swinbank]

Hello,

I'm trying to use MailMate r5875 with Office365 using OAuth2 to authenticate for both IMAP and SMTP.

IMAP works fine. When I use SMTP, the server refuses MailMate's attempt to authenticate as follows:

  11:17:22 Retrieving password (keychain or user request)
  11:17:22 C: AUTH XOAUTH2 ••••••••••
  11:17:27 S: 535 5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Tenant. Visit https://aka.ms/smtp_auth_disabled for more information. [AM4PR0701CA0035.eurprd07.prod.outlook.com]
  11:17:27 Error: Unexpected return code 535 (expected 235): “5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Tenant. Visit https://aka.ms/smtp_auth_disabled for more information. [AM4PR0701CA0035.eurprd07.prod.outlook.com]”.
  11:17:27 Error code: 2000

(There's a full log of the session at the bottom of this mail in case that's helpful).

My employer has provided special instructions for configuring Evolution on Linux to work with our Office365 system. These include overriding the Tenant and Application ID settings — there's an example of what that looks like at https://urchin.earth.li/~jds/evolution-oauth2.png. Perhaps something similar is necessary in MailMate - is that possible?

Any ideas or suggestions much appreciated!

Cheers,

John



11:17:21 Handling request
11:17:21 Ready to run action (type: 0, retry count: 0)
11:17:21 Clearing connection to smtp.office365.com
11:17:21 Trying to connect to smtp.office365.com on port 587 (CFNetwork) with STARTTLS (required)
11:17:22 Resolved hostname (smtp.office365.com).
11:17:22 Successful connection.
11:17:22 Ready for reading.
11:17:22 S: 220 AM4PR0701CA0035.outlook.office365.com Microsoft ESMTP MAIL Service ready at Sun, 6 Mar 2022 11:17:21 +0000
11:17:22 C: EHLO [192.168.1.106]
11:17:22 S: 250-AM4PR0701CA0035.outlook.office365.com Hello [87.210.54.76]
11:17:22 S: 250-SIZE 157286400
11:17:22 S: 250-PIPELINING
11:17:22 S: 250-DSN
11:17:22 S: 250-ENHANCEDSTATUSCODES
11:17:22 S: 250-STARTTLS
11:17:22 S: 250-8BITMIME
11:17:22 S: 250-BINARYMIME
11:17:22 S: 250-CHUNKING
11:17:22 S: 250 SMTPUTF8
11:17:22 C: STARTTLS
11:17:22 S: 220 2.0.0 SMTP server ready
11:17:22 Initiating secure connection...
11:17:22 Prepare secure connection...
11:17:22  Returned (4)...
11:17:22 Protocol version: kTLSProtocol12
11:17:22 C: EHLO [192.168.1.106]
11:17:22 S: 250-AM4PR0701CA0035.outlook.office365.com Hello [87.210.54.76]
11:17:22 S: 250-SIZE 157286400
11:17:22 S: 250-PIPELINING
11:17:22 S: 250-DSN
11:17:22 S: 250-ENHANCEDSTATUSCODES
11:17:22 S: 250-AUTH LOGIN XOAUTH2
11:17:22 S: 250-8BITMIME
11:17:22 S: 250-BINARYMIME
11:17:22 S: 250-CHUNKING
11:17:22 S: 250 SMTPUTF8
11:17:22 Retrieving password (keychain or user request)
11:17:22 C: AUTH XOAUTH2 ••••••••••
11:17:27 S: 535 5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Tenant. Visit https://aka.ms/smtp_auth_disabled for more information. [AM4PR0701CA0035.eurprd07.prod.outlook.com]
11:17:27 Error: Unexpected return code 535 (expected 235):
“5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Tenant. Visit https://aka.ms/smtp_auth_disabled for more information. [AM4PR0701CA0035.eurprd07.prod.outlook.com]”.
11:17:27 Error code: 2000
11:17:27 Failed action (0). Reset observed read/write timeouts: 8/8
11:17:27 Handling reply
11:17:57 Handling request
11:17:57 C: QUIT
11:17:57 S: 221 2.0.0 Service closing transmission channel
11:17:57 Clearing connection to smtp.office365.com
11:17:57 Ready to run action (type: 3, retry count: 0)
11:17:57 Clearing connection to smtp.office365.com
11:17:57 Ready to run action (type: 3, retry count: 0)
11:17:57 Clearing connection to smtp.office365.com
11:17:57 Completed action (3). Observed read/write timeouts: 8/8
11:17:57 Handling reply