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Outlook 2010 stuck on "Trying to connect.." error

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Our migration to Office 365 has been working out very well, but I have two clients that haven't been able to connect in the last day or two. One sees  "Trying to connect.." almost continuously and cannot send, while the other user sees this intermittently.  Both have Outlook 2010, and have 3-5 accounts connected. Other users on the same network with a similar configuration have no issue.


What sort of troubleshooting can I do to determine what is causing this issue?

All Replies
  • Hello nsideras-HBF,

    There are several troubleshooting steps that can cause these issues, the most comprehensive list can be found at:

    Thank you, Jeff McDonald, O365 Forum Moderator

  • Hello nsideras-HBF,

    Are your users still having issues?

    Thank you, Jeff McDonald, O365 Forum Moderator

  • Hello,

    Can you also confirm you have created an ADFS Proxy? Without the Proxy Service, the Outlook connection endpoints will not connect to Office 365 services even from within the internal network.  This is because the Outlook endpoint does not make use of the Passive Responder Profile, and requires an AD FS Internet presence (AD FS Proxy server) to function properly. This URL will better help you configure your environment:

  • David,  We do not use SSO, so as far as I know that is not relevant. Thank you for checking in though.


    Jeff, I am still having issues, but I've been getting some responses from Microsoft support via email. We're past the initial troubleshooting now, so I'm hoping to resolve this over the phone with them tomorrow. Thanks for asking.

  • Let me know if you resolved this issue and how. having similar issues.

  • Hi - I'm having the exact same frustrating issues - did you have any luck with a resolution to this?

    Many thanks.