unable to send email with Oauth2, but can read email via IMAP
Reported by David Lim | October 12th, 2022 @ 06:12 AM
My school email (personal) which uses office365 converted to
only "Modern Auth" on Oct 1, 2022.
Since then I can read my email via IMAP just fine. But I can't send
email (via SMTP).
Here is the Activity Viewer for SMTP when I attempt to send the message:
05:31:10 Handling request
05:31:10 Ready to run action (type: 0, retry count: 0)
05:31:10 Clearing connection to outlook.office365.com
05:31:10 Trying to connect to outlook.office365.com on port 587
(CFNetwork) with STARTTLS (required)
05:31:10 Resolved hostname (outlook.office365.com).
05:31:10 Successful connection.
05:31:10 Ready for reading.
05:31:10 S: 220 PH0P220CA0011.outlook.office365.com Microsoft ESMTP
MAIL Service ready at Wed, 12 Oct 2022 05:31:10 +0000
05:31:10 C: EHLO [10.81.234.15]
05:31:10 S: 250-PH0P220CA0011.outlook.office365.com Hello
[136.52.124.238]
05:31:10 S: 250-SIZE 157286400
05:31:10 S: 250-PIPELINING
05:31:10 S: 250-DSN
05:31:10 S: 250-ENHANCEDSTATUSCODES
05:31:10 S: 250-STARTTLS
05:31:10 S: 250-8BITMIME
05:31:10 S: 250-BINARYMIME
05:31:10 S: 250-CHUNKING
05:31:10 S: 250 SMTPUTF8
05:31:10 C: STARTTLS
05:31:10 S: 220 2.0.0 SMTP server ready
05:31:10 Initiating secure connection...
05:31:10 Prepare secure connection...
05:31:10 Returned (4)...
05:31:10 Protocol version: kTLSProtocol12
05:31:10 C: EHLO [10.81.234.15]
05:31:10 S: 250-PH0P220CA0011.outlook.office365.com Hello
[136.52.124.238]
05:31:10 S: 250-SIZE 157286400
05:31:10 S: 250-PIPELINING
05:31:10 S: 250-DSN
05:31:10 S: 250-ENHANCEDSTATUSCODES
05:31:10 S: 250-AUTH LOGIN XOAUTH2
05:31:10 S: 250-8BITMIME
05:31:10 S: 250-BINARYMIME
05:31:10 S: 250-CHUNKING
05:31:10 S: 250 SMTPUTF8
05:31:10 Retrieving password (keychain or user request)
05:31:10 C: AUTH XOAUTH2
••••••••••
05:31:19 Waited 9 seconds on read.
05:31:19 S: 535 5.7.139 Authentication unsuccessful,
SmtpClientAuthentication is disabled for the Mailbox. Visit
https://aka.ms/smtp_auth_disabled
for more information. [PH0P220CA0011.NAMP220.PROD.OUTLOOK.COM]
05:31:19 Error: Unexpected return code 535 (expected 235):
“5.7.139 Authentication unsuccessful,
SmtpClientAuthentication is disabled for the Mailbox. Visit
https://aka.ms/smtp_auth_disabled
for more information.
[PH0P220CA0011.NAMP220.PROD.OUTLOOK.COM]”. 05:31:19 Error
code: 2000
05:31:19 Failed action (0). Reset observed read/write timeouts:
8/8
05:31:19 Handling reply
For my IMAP Account Settings:
IMAP Server: outlook.office365.com
Require SSL: enabled
Oauth2: enabled
SMTP Server: outlook.office365.com
Require SSL: enabled
Oauth2: enabled
If I use Apple Mail, it works.
I deleted all the keychain entries for "mailmate" that had exchange
in it,
signed out "everywhere" for my office365 account at office.com.
To no avail.
I actually have another office365.com account for work.
My work just migrated to using office365, and I'm experiencing the
same issue
with it. I can read my email with IMAP, but can't send email via
SMTP.
Same error message as above.
Comments and changes to this ticket
-
benny October 20th, 2022 @ 03:49 PM
Apple Mail uses the native Exchange protocol which means it doesn't use the same “method” for sending as MailMate does. The error message seems to indicate that your service providers have disabled SMTP even when using “modern authentication” (OAuth2). I think you should try asking them if SMTP is supposed to work when using OAuth2. They do allow IMAP using OAuth2 so I don't see why they wouldn't allow SMTP.
If you want to try something comparable with MailMate then you can try to see if you can send using Thunderbird.
-
David Lim October 24th, 2022 @ 03:21 PM
Just fyi,
Per your suggestion I tried T-bird, and sure enough it failed to send emails too.
Login to account "Office365(Microsoft)" failed Login to server smtp.office365.com with username xxx@xxx.com failed
I had our IT person look at Exchange settings.
And he found that Authenticated SMTP was disabled for all our users.
He was pretty sure it was enabled, but somehow got disabled. He thinks it may
have happened when MS disabled basic authentication globally on Oct 1, 2022.In short, he re-enabled Authenticated SMTP, and I can once again send email via Mailmate
(thank goodness!!!)This ticket can be closed.
-
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Mac OS X email client.
benny