#3023 reproduced
Jonathan Latner

Outlook with mailmate

Reported by Jonathan Latner | March 8th, 2022 @ 07:58 AM

I cannot connect mailmate with outlook. When I create the account, mailmate connects me with my default browser. A webpage open that asks, "Are you trying to sign in to MailMate?" I click Continue. I am then returned to the mailmate application, but the process repeats itself, endlessly without actually creating a Mailmate mailbox for outlook.

Comments and changes to this ticket

  • benny

    benny March 8th, 2022 @ 03:33 PM

    First try updating: Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane to get the latest test release.

    If it still fails, use “Help > Send Feedback” to send me a screenshot of your account settings.

  • Sanchit

    Sanchit March 11th, 2022 @ 03:13 PM

    I'm also facing this issue. My MailMate setup stopped working today with my Outlook.com account, it asks to "Authorize MailMate to access email for <> at "imap.outlook.com"." and the authorization in the browser is successful but MailMate pops up the same dialog again.

    I updated to latest 5875, tried outlook.office365.com as the IMAP server and smtp.office365.com/smtp-mail.outlook.com as the SMTP server, overrode the ports but it still didn't work.

    New Server settings tried from:

    Activity Viewer:
    15:18:58 Clearing connection to imap-mail.outlook.com
    15:18:58 Ready to run action (type: 1000, retry count: 0)
    15:18:58 Clearing connection to imap-mail.outlook.com
    15:18:58 Trying to connect to imap-mail.outlook.com on port 993 (CFNetwork) without STARTTLS (required)
    15:18:58 Resolved hostname (imap-mail.outlook.com).
    15:18:58 Prepare secure connection...
    15:18:58 Successful connection.
    15:18:58 Initiating secure connection...
    15:18:58 Returned (4)...
    15:18:58 Protocol version: kTLSProtocol12
    15:18:58 S: * OK The Microsoft Exchange IMAP4 service is ready. [***]
    15:18:58 C: A0 CAPABILITY
    15:18:58 S: A0 OK CAPABILITY completed.
    15:18:58 Retrieving password (keychain or user request)
    15:18:58 C: A1 AUTHENTICATE XOAUTH2 ••••••••••
    15:19:05 S: A1 NO AUTHENTICATE failed.
    15:19:05 Error: Server response: “A1 NO AUTHENTICATE failed.”. Command attempted: “A1 AUTHENTICATE XOAUTH2 ••••••••••”.
    15:19:05 Retrieving password (keychain or user request)
    15:19:05 Error code: 12
    15:19:05 Failed action (1000). Reset observed read/write timeouts: 8/8

    15:19:05 Handling reply
    15:19:55 Terminating non-running connection...
    15:22:00 Running action
    15:22:00 Handling request
    15:22:00 Trying to disconnect nicely (30)...
    15:22:00 C: R2 LOGOUT
    15:22:00 Error: Connection error (Broken pipe).
    15:22:00 Clearing connection to imap-mail.outlook.com
    15:22:00 Ready to run action (type: 3, retry count: 0)
    15:22:00 Disconnecting
    15:22:00 Clearing connection to imap-mail.outlook.com
    15:22:00 Completed action (3). Observed read/write timeouts: 8/8

    15:22:00 Handling reply

  • Jonathan Latner

    Jonathan Latner March 11th, 2022 @ 03:15 PM

    The solution for me was to use an application specific password.

  • benny

    benny March 11th, 2022 @ 08:51 PM

    It appears it'll work for most/all users when disabling OAuth2 and using an application specific password instead, but for the record I have a test account for which it does work with OAuth2. I use imap-mail.outlook.com and smtp-mail.outlook.com and the full email address as username. I guess it might help if you open “Keychain Access” and locate/delete the tokens matching com.freron.MailMate.Outlook.*-token. This will force MailMate to completely start over with OAuth2. Let me know if that helps.

  • Sanchit

    Sanchit March 12th, 2022 @ 10:45 AM

    Deleting the tokens fixed it, thanks! Was trying to avoid going the app password route.

  • benny

    benny April 20th, 2022 @ 12:47 PM

    • State changed from “new” to “reproduced”

    @Sanchit: Thanks for confirming “the fix”. I'll have to think about how to best handle this.

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