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SMTP for POP3 not working on Outlook 2016 - O365

Michael Serrano 21 Reputation points
2021-02-16T20:29:57.203+00:00

I recently purchased Action Pack and set up the O365 application. Online everything works fine for Outlook. On Outlook desktop 2016, when setting up POP3 and testing the connection, I can receive but cannot send. It is giving me an authentication error for SMTP.

The password and settings are correct, but I still can't send. Any ideas?

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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  1. Andy David - MVP 150.4K Reputation points MVP
    2021-02-16T20:45:39.63+00:00

    Have your admin ( or you if you have the rights)
    verify that SMTP auth is allowed in your tenant or on your mailbox

    https://learn.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission

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  1. Michael Serrano 21 Reputation points
    2021-02-16T23:03:34.417+00:00

    Thank you @Andy David - MVP this was helpful. Basically, I had to turn off SMTP Auth and turn it back on for it to work correctly. Very odd that it didn't configure correctly during set up.

  2. Michael Serrano 21 Reputation points
    2021-02-17T21:18:19.447+00:00

    @Jade Liang-MSFT Thanks.

    The funny thing is that it stopped working again and I can't send from O365 either. When I send on O365 I get a bounce back that my email was blocked. It happens to anyone I send to. Here's a sample message:

    Delivery has failed to these recipients or groups:

    michael.serrano@axis .com
    Your message wasn't delivered because the recipient's email provider rejected it.

    I put in a ticket with Microsoft.

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