Outlook is not updating automatically
One of the senior managers has a 5GB mailbox, the others are 1GB or less.
The issue only happens when we add the 5GB mailbox is added.
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.
This message doesn't mean that the mail server doesn't support encryption, it just means Outlook's Auto Account Setup can't determine the correct settings to use.
This is caused by incomplete or missing autodiscover records in DNS.
Sometimes I can remove the mailbox and re-add it and it starts working but not always.