2010 outlook connecting to office 365

Chrisman, Rich 1 Reputation point
2021-10-22T18:02:18.997+00:00

I cannot get an outlook, 2010 client, to connect to office 365 via any avenue. I tried the straight-through approach using auto-discovery.
Did not work.
I tried the proxy HTTP way.
I get "there is a problem with the proxy's certificate. It does not match the target site of outlook.office365.com.
Unable to connect to the proxy server.
Please help.

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. 吕润泽(MarkLv) 1 Reputation point
    2021-10-23T10:27:07.397+00:00

    Office2010 will not support O365 connection soon, please upgrade to the latest version of Office2016 or 2013

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  2. Yuki Sun-MSFT 40,646 Reputation points
    2021-10-25T07:03:28.463+00:00

    Hi @Chrisman, Rich ,

    Could you have a check via File > Help > About Microsoft Outlook and see which build of Outlook 2010 you are running?

    I just tried adding an Microsoft 365 email account into Outlook 2010 (14.0.7268.5000) and it can be configured successfully:
    143332-1.png

    For your situation, please ensure all the available updates for Outlook 2010 have been patched.

    In addition, based on my research, please go to the “Internet options” in the control panel, or you can press Win+R to open the Run command box, and type "inetcpl.cpl", press Enter to quickly open the "Internet Properties" diablogue box. Then click the Connections tab, choose "LAN settings",make sure the checkbox of "Use a proxy server for your LAN" is NOT selected:
    143372-2.png

    Furthermore, Outlook 2010 has reached its end of support since last year and is no longer listed as a supported version of Office are supported for connecting to Microsoft 365 (and Office 365) services. (For the supported versions of Office, you may refer to: Office versions and connectivity to Microsoft 365 services.) Also according to this official blog, "after November 1, 2021, only Outlook 2013 Service Pack 1 (with latest fixes) and later will be able to connect to Microsoft 365 services". So as was mentioned above by MarkLv, it is highly recommended to update to a supported version of Outlook as soon as possible.


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  3. Chrisman, Rich 1 Reputation point
    2021-10-28T13:17:13.723+00:00

    I verified the version (the same version you except the user has 32 bit).
    When I try to do the automatic connect, it just freezes and crashes. I attempted a repair on outlook but did not resolve the issue. Any ideas?

    Error message when I try to use IMAP:

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  4. Chrisman, Rich 1 Reputation point
    2021-10-28T13:19:09.307+00:00

    144604-error.png

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  5. Andy David - MVP 139.8K Reputation points MVP
    2021-10-28T13:47:54.97+00:00

    If your tenant required Modern Authentication, this wont work. You will need to verify that.

    https://learn.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/disable-basic-authentication-in-exchange-online

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