testconnectivity.microsoft.com does not work anymore - SSL negotiation error

BK IT Staff 246 Reputation points

We have been experiencing a problem with the tool for a few weeks now. We've been using it for years without any issues.

Basically, either that I use it for ActiveSync or Outlook Anywhere connectivity tests, I get the same error message:


"The certificate couldn't be validated because SSL negotiation wasn't successful. This could have occurred as a result of a network error or because of a problem with the certificate installation."

My users seem to not have any problems when using Exchange services (OWA, ActiveSync, Outlook anywhere).

Since I've been struggling on this issue for a few days now, can you give me some advice on where to look to guess what the problem is? What I can tell is:

-Did not make any firewall/networking changes that I'm aware of.
-Did not install any updates on Exchange, nor I made any changes to the configuration.
-My cert is valid and current.

Perhaps, could it be due to some change to the tool itself (cipher suites, tls protocols etc)?

Thank you,

Exchange Server Management
Exchange Server Management
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Accepted answer
  1. Xzsssss 8,861 Reputation points Microsoft Vendor

    Hi @BK IT Staff ,

    Please also check the Outlook Connectivity with Autodiscover.
    BTW, what's the version of your server?

    I could successfully test it with Autodiscover, but the ActiveSync failed with some SSL errors.
    I think some parts of the programming of EXRCA could be wrong, if your system is running correctly, just ignore the test result.

    Best regards,

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  1. Jonathan Holloway 11 Reputation points

    I am experiencing the same result, without changes. I too am suspecting SSL/TLS/Cipher changes are at play.

    2 people found this answer helpful.

  2. BK IT Staff 246 Reputation points

    Hi @Xzsssss , I ran the autodiscover test with Outlook 2016 (the test that you can run by doing ctrl+right click on outlook icon in the systray) from a laptop connected through my mobile hotspot to simulate an external connection request. No issues at all.

    My Exchange version is 2013 CU23.

    So, I will ignore the exRCA errors in the future, though I hope the exRCA developers will fix the issue asap, since that tool is really useful when you need somthing on the go for testing Exchange issues.

    Thank you.

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  3. DION Jean-Michel 6 Reputation points


    The test failed only on EXRCA.
    Outlook test Email autoconfigurations work.

    I use EXRCA for testing an hybrid setup.

    I think too it's an issue with EXRCA.


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  4. 2021-09-15T09:31:52.457+00:00

    Same problem here with Exchange 2013.

    I'm also experiences that setting up new Outlook profiles won't work outside the building. So I think there's definitely a problem with autodiscover. Couldn't found out what it is yet.