Troubleshooting email integration errors

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  • NewWave Tech

    Hi team,

    Sell shows a below error message.

    May I know how to fix it?

  • Beau P.
    Zendesk Customer Care

    Hello Joseph,

    If you have an Outlook account, make sure you're using the Sign in with Microsoft option as opposed to entering the email/password directly as this should yield better results.

    Beau | Customer Advocate

    Ask our Zendesk Community

  • Petar Weigand

    I have received  "Authentication: cannot authenticate." although SMTP AUTH is enabled for my mailbox and for my whole organization (see the attached screenshot). Is there something else that could cause this error?

  • Cheeny Aban
    Zendesk Customer Care

    Hi Petar Weigand,

    Here's the Resolution steps,

    1. The Office 365 email admin needs to enable SMTP AUTH on your Office 365 email account.
      For more information, see the article: Use the Microsoft 365 admin center to enable or disable SMTP AUTH on specific mailboxes.

    2. After enabling the email protocol, follow the steps to integrate your Office 365 email.

    More information can be found here: When I try to "Sign in with Microsoft" I am getting a "Cannot Authenticate" error message


  • Petar Weigand

    Hi Cheeny,

    this is exactly what I did and those are screenshots from which you can see that SMTP AUTH is enabled on both my mailbox and my whole Office365 tenant but this didn't help.

    Is there something else I can do or is there some additional troubleshooting logs which would provide a more detailed error message?

  • Cheeny Aban
    Zendesk Customer Care

    Hi Peter,

    For advanced troubleshooting, I suggest that you reach out to our Customer Support so they can have a better look into your account.


  • Mark Szymanski


    The error message we get does not have a number.  Using the sign-in with Google option, we get:

    Integration with your account failed with the following error codes:
    • authentication: Login/password invalid
    • Please make sure that IMAP access is enabled in your email settings

    We use Gmail with Okta as single sign-on.  My admin tells me have IMAP disable (in Google Workspace) for security compliance.  Can we integrate via SMTP, and if so, how?  If not, is there another way ZD would recommend?


  • Lionel

    Unable to log in to sync my email.

  • Gabriel Manlapig
    Zendesk Customer Care
    Hi Lionel,

    The error message Authentication: Cannot Authenticate indicates that the authorization of our OAUTH application on the Office 365 side was successful. However, when we tried to use the provided credentials to log in to the server to verify that the integration is successful, we ran into an SMTP AUTH error. 

    For more information, please follow this article: When I try to "Sign in with Microsoft" I am getting a "Cannot Authenticate" error message

    I hope this helps. Thank you!

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