The message that comes up when Outlook can't set up an encrypted connection automatically caught a couple of users off guard this week.After calling their mail provider to verify the account supports encryption, they asked me what was wrong with Outlook.You'll need to enter your account information and server names then click More Settings and configure your SSL or TLS settings on the Advanced tab.A Microsoft Outlook Most Valuable Professional (MVP) since 1999, Diane is the author of several books, including Outlook 2013 Absolute Beginners Book.The certificate error that pops up shows you that it is finding the certificate on your company’s public website. Why the error and why is it showing the company’s public website’s certificate.Well first, let’s explore a little on the steps External Autodiscover goes through in order to find Exchange.It was designed to work like the traditional MSI installation.With the introduction of two-factor authorization since the original date of this article, there is a second (and becoming more common) cause of this error: Outlook needs the app password, as it will not currently bring up the second authorization screen.
When you first launch your Outlook client (Outlook 2007 or above required for Autodiscover access), it will search Active Directory for a Service Connection Point (SCP) record.
I have a blog post on Outlook Certificate Errors which applies to Outlook 2007, Outlook 2010, and Outlook 2013. That blog post describes an incorrect certificate on Exchange itself.
For example, you make a connection to Exchange and your Internal URLs, External URLs, and Autodiscover Service Internal URI FQDN is not defined on the certificate.
This will install the traditional Office suite, which is recognized by other applications.
Note: All Office 2013 suites sold "retail" are "click to run".