In the above link, this issue was covered and I thought that the constant credential requirement in Outlook was just my issue. I have since found out that many people are starting to experience the constant outlook popup asking for password. I have fixed several temporarily by re-adding the computer to the domain. I also notice that when I am in Outlook, I have no access to the out of office replies, but I can work fine in OWA. I have tried everything even creating a new user ID and connecting my mailbox to this new user and the problem does not happen as often but it still happens. I was reading somewhere that this has a lot to do with Autodiscover.
I ran the remote connectivity analyzer for Outlook connectivity and Autodiscover connectivity and both failed. So now I figured that it may have something to do with the configuration of Autodiscover. I just can't seem to figure out what I need to do. I have had this server up and running for 2 years with no issues. My certificates are correct and up to date, so I have no idea what and why this just started happening. I was going to update to SP3, but saw that Microsoft pulled it for problems. I don't need that, so I am not going to do it until it is clear of problems.
I checked the IIS manager and when I tried to run a test connection on the Default website - autodiscover, I get an error message when I select Basic Settings..
I really hope that someone can assist me with this before it gets too much to handle.