[MlMt] Office365 SMTP / OAuth2

[Alexandre Takacs]

I am also having various issues with MM & SMTP…

I eventually managed to make it work by _not_ using OAUTH2, which is 
supported but not a 365 default. It would have admin right on your 
tenant it is pretty simple to change.

That being said it would seem that your account is not authorised -at 
all- for SMTP sending, as per 
https://docs.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission




On 6 Mar 2022, at 12:41, John Swinbank wrote:

> 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
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