[MlMt] Office365 SMTP / OAuth2

[Info@techworkspro.com]

FWIW, I use AWS SMTP Account for my business account instead of my server for the benefit of SES features. No problems with that and App-specific (M-M) PW. 

M$ 365… Ugh. 

Henry
- -
Please excuse the tttapping errors... 
Sent from my iPhone
C/T (954) 253-4125
Henry M. Seiden
Techworks Pro


> On Mar 6, 2022, at 11:03, Alexandre Takacs <a.takacs at augicom.ch> wrote:
> 
> 
> 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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