[MlMt] Office365 SMTP / OAuth2

[John Swinbank]

Hello,

Thanks for your comments!

> 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

I have been speculating (maybe better: hoping) that since this is specified on an organization-wide basis that overriding the Tenant ID (as per instructions from my employer) might do the trick here. I've not found a way to do this in MailMate, though.

Cheers,

John




On 6 Mar 2022, at 17:03, Alexandre Takacs 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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