When using Outlook or ActiveSync you may see Security Alerts dialog box.

Outlook for Windows

The information you exchange with this site cannot be viewed to change by others. However, there is a problem with the site’s security certificate.

Error

There are 7 variations of this error:

  • Red X next to The name on the security certificate is invalid or does not match the name of the site.
  • Red X next to The security certificate has expired or is not yet valid.
  • Red X next to The security certificate was issued by a company you have not chosen to trust.
  • Two red X next to The security certificate has expired or is not yet valid and The name on the security certificate is invalid or does not match the name of the site.
  • Two red X next to The security certificate was issued by a company you have not chosen to trust and The security certificate has expired or is not yet valid.
  • Two red X next to The security certificate was issued by a company you have not chosen to trust and The name on the security certificate is invalid or does not match the name of the site.
  • Tree red X next to all certificate checks.

Outlook for Mac

On Mac computers you may see the dialog box with the following wording: 

A secure connection cannot be established with the server because its intermediate or root certificate cannot be found. 
Error on mac

ActiveSync

On mobile devices you can see the following errors:

  • iOS devices
    iOS devices
  • Android devices
    Android devices

Resolution:

All users are affected:

  • Check you have correct autodiscover record configured for your domain. Find correct autodiscover record in HostPilotĀ® Control Panel > Home > Exchange Servers & Settings. Verify autodiscover.yourdomain.com resolves to the same value globally (e.g. via MXToolBox website).
  • If you have the website running on youdomain.com, check your website has appropriate certificates installed. Browse https://yourdomain.com. If it returns SSL certificate error, contact your web-developer and request SSL certificate to be installed or updated.
    SSL
    As the workaround you may add correct autodiscover entry to HOSTs file: read the Knowledge Base article on How Do I Find And Modify Entries In The HOSTS File?
  • If you have the website running on yourdomain.com, check how your website deals with .XML files. When Outlook is looking for autodiscover record it checks https://yourdomain.com/autodiscover/autodiscover.xml, some websites are configured to process requests to yourdomain.com/something/etc… with the particular response. If Outlook receives the response with any .XML file, it considers autodiscover is found when actually it does not. Contact your web developer and request to make appropriate changes (e.g. set website responses with Page Not Found).
  • Check whether you have local autodiscover setup in your Domain Name System. Read the Knowledge Base article on How Do I Disable Autodiscover For On-Premise Exchange?

One user / particular machine is affected:

  • Check you have the correct date, time and time zone setup on the affected machine.
  • Check autodiscover resolves correctly on the affected machine. Open Command Prompt and type in ping autodiscover.yourdomain.com. It should return correct autodiscover IP address. You may find correct autodiscover value under HostPilot > Home > Exchange Servers & Settings. Ping autodiscover server and compare IP addresses.
    Ping
    If they do not match:
  • Click on View Certificate… on error window, add the mentioned certificate to the trusted ones in Certificate manager: Start > in search field type in certmgr.msc > press Enter > find mentioned certificate and move it to Trusted Root Certification Authorities > Certificates directory.
    CertMng

If you cannot resolve the issue, provide support with the following info: