MAC Outlook does not change connection profiles

Hello, I'll start by saying I'm not very MAC literate. I have an exchange 2010 environment with one mac user running outlook 2011,

When the user is in the office his outlook connects to the exchange server using the server name and it operates fine.  it connects to servername.domainname.local/EWS/.... When he leaves the office, it does not automatically change to the internet based access using the public url Use SSL is checked in the outlook server setup.

if he manually changes it to, it works, so it's not automatically changing connection types.

This works fine on PC's running outlook, users can come and go to between the office and out of the office with no problem. It's just the mac that is experience this issue.

Is there any settings either on the mac, mac outlook or exchange that need to be made for the MAC?
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Gareth GudgerSolution ArchitectCommented:
You can reconfigure Exchange to use the same names internally as it does externally. In fact when your certificate expires you will likely have to drop the .local names anyway. Third party certificate providers no longer accept them on UC certs. Its easy to do.

Check out this article.
ChiITAuthor Commented:
This may be timely since my ssl certificate expires next month and I need to renew it.

Will changing the names to be the same have any effect on the PC users? Also will dropping the .local have any other impact that I would need to worry about?
Gareth GudgerSolution ArchitectCommented:
None at all. Take a look at that article. It explains the entire process. You will also need to configure split-brain DNS if you don't have it already. I use this same method all the time for pure PC networks.

With this new requirement from the 3rd party cert providers I am currently making this transition quite often for my clients and without incident.
Determine the Perfect Price for Your IT Services

Do you wonder if your IT business is truly profitable or if you should raise your prices? Learn how to calculate your overhead burden with our free interactive tool and use it to determine the right price for your IT services. Download your free eBook now!

ChiITAuthor Commented:
Hi Gareth, getting back to this. You had mentioned I'd most likely have to drop the .local. I noticed that there are configs such as the outlook server name in the outlook mail config for example that point to

Will these automatically resolve if the .local is removed? I'm guessing its part of the ad as well..

P.s. I tried to send a note regarding hiring you but can't tell if it went through.
Gareth GudgerSolution ArchitectCommented:
Sorry for the delay. Crazy work week.

Yes, you can drop the .local's. The SSL certificate providers will no longer accept .local on a certificate request. So, with .local removed from the cert we need to change all Exchange URLs (both internal and external) to names that are allowed on the cert. Which will be your .com's etc. Then we configure split-brain DNS so your internal computers go to .com versus .local.

Hope that helps. Let me know if any of the steps in that article I linked earlier don't make sense.
ChiITAuthor Commented:
HI Gareth, thanks, would it be possible for you to contact me via message for a possible hire for remote work?
Gareth GudgerSolution ArchitectCommented:
Sounds good. Talk to you soon.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
ChiITAuthor Commented:
Gareth was able to help me install new SSL certificates which corrected the problem
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Mac OS X

From novice to tech pro — start learning today.