Microsoft Outlook 2013 (Office 365) & Security Certificates

I have MS Outlook 2013, part of the MS Office 365 suite installed on a Win 8.1 64 bit machine. That work fine. I have it configured to connect to my Dreamhost account. The incoming IMAP port is set at 143 (TLS) and the outgoing port is 25 (TLS). That all works fine.

The problem is when I first start up Outlook. It complains about “Internet Security Warning”. The problem is that Dreamhost won’t purchase a proper certificate. This is basically unacceptable and they should make potential clients aware of this problem from the very beginning. However, I cannot do anything about that at the present since this is a small government account. Until then, I have to find a way to make Outlook happy. All of the users here are complaining (loudly). I have tried importing the certificate but the problem does not go away, In fact, I am just presented with certificate after certificate until I finally get tired and just click OK. Does anyone here have a working solution for this problem?

The simplest solution to this can be found here:
in the section titled “Direct Server”

Check you domain hosting ssl provider and make sure the imps and pop will configure properly with Outlook 2013.

It will happens with Microsoft if your hosting provide free ssl. Or try to install custom ssl like letsencrypt.

Still getting the error then check and contact with Outlook Support.