Certificate error popping up; outlook.com
Hi all,

Recently our company started incorporating Office365. Since a while now ( two weeks or so ) we experience errors every now and then. The errors are ourlook.com certificate errors. We have our mail on the Office365 platform and access it mainly via Outlook. Now our Outlook randomly (not only at startup but during work as well) pops up the certificate error window; "outlook.office365.com ; The security certificate was issued by a company you have not chosen to trust. ...")

When looking at the certification path it shows that it is self-signed !?! So no chain of certificates.

MS Support desk told me to install the certificate but in my opinion Office365 (outlook.com certificate to be precise) should not be self-signed since it's a online service. Beside my opinion, does anybody know how to get rid of these errors in another way then installing the certificate? Preferably by telling Microsoft to buy a certificate from a CA :-)

Regards,

Pascal
June 29th, 2015 2:58am

Hi,

Based on the error message you encountered, I found a blog below:

Error message when you try to configure Office 365 account in Outlook: "The security certificate was issued by a company you have not chose to trust"

The issue occurs because the network incorrectly redirects external auto-discover calls back to your Client Access Server(CAS) that are deployed on-premise. You can refer to the blog and check if the resolution is suitable for you.

Regards,

Melon Chen

Forum Support

Free Windows Admin Tool Kit Click here and download it now
June 30th, 2015 3:18am

Hi,

Thanks for your reply. On one machine i will set up this different mail configuration, but i believe that this does not fix the issue. The certificate is from outlook.com and not from a local CAS.

Regards,

Pascal

July 1st, 2015 3:57am

On one machine i will set up this different mail configuration

Hi,

Does it work?

Regards,

Melon Chen

Forum Support

Free Windows Admin Tool Kit Click here and download it now
July 2nd, 2015 3:47am

Hi,

Sorry for the delay but it didn't work. It still pops up once in a while. Any thoughts?

Regards,

Pascal

July 22nd, 2015 1:45am

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