cant connect outlook to exchange 2013

I agree with Maclean. I would get the UC / SAN certificate from a third party provider. Its going to save you a lot of heartache.

The cost of the cert easily offsets your time.

Whole process on namespace, certs and DNS documented here.
http://supertekboy.com/2014/07/08/designing-simple-namespace-exchange-2013/

Self-signed should work just fine.  

Go to your exchange server and export the trusted root certificate for your exchange server and install it on the workstation.
Start > mmc > File >  add snap-in > certificates > add> computer account > next > local computer > finish > ok
find you exchange server name > right click > all tasks > export > next > next > name it > finish.
Then import it on your workstation pretty much reversing what I just showed you.

Hi,

Check this article from Technet and its resolved, i am suggesdting this solution based on the screenshots you shared.

Outlook gives an error for Proxy Server Certificate

I guess this will resolve the issue, if not feel free to shout back!

Also try this KB http://support.microsoft.com/kb/923575

Hi Guys
Thanks for all posts and support,
I think I could resolve the issue, I purchased new SSl certificate and installed, changed iis and SMTP services to new certificate and now outlook connects. Its really strange even self signed certificate didn't work.
Thanks again and I will keep posted if I find any further issue.
Kind regards
Biju

hi Guys
Just want to let you know Now I am getting a different error on out look. I have new SSl certificate install on server and outlook started working but still getting certificate warning. and on outlook 2013 edition I get proxy server error every time I open outlook. Please see attachments. Outlooks works ok but always error comes in...
can help?
kind regards
Biju
Capture.JPG
2.JPG

Thanks Maclean
Please find the attachment , i am getting that error when trying to  test-outlookwebservices command.
thanks
1.JPG

yes, did same and disable all firewall, still same error..

So when you say you "did the same", you meant you checked if the "extest_6df7519dae1e4" user/mailbox already existed, or you created it manually for testing purposes?
I have had some issues at times in the past creating the account myself, but usually they are simple to fix.

Perhaps have a look at this suggestion. You could open up the PS1 file, copy it for backup, and amend the original as per below suggestion

http://www.definit.co.uk/2011/03/exchange-2010-createtestuser-mailbox-could-not-be-created-verify-that-ou-users-exists-and-that-password-meets-complexity-requirements/

As Gareth recommends as well check that all your internal links are ok
You can locate this on the server section under virtual directories.

I had to create "extest_6df7519dae1e4" manually. It was not there. but even creating manually it showed same error. Ok I will try as you said above. and I made changes according to http://supertekboy.com/2014/07/08/designing-simple-namespace-exchange-2013/ and all my internal URLs are now same as external including auto discover. but error stays as it was.
So I strongly believe there is something missing in my SSl certificate. I might ask to reissue again with current settings.
one question before I create new CSR.
when creating certificate request in auto discover section intranet it shows as " autodiscover.secure.mydomain.com.au" ( which is my external domain), but in auto discover internet it is " Autodiscover.mydomain.local,Autodiscover.mydomain.com.au" ( "secure" not showing there) is that correct or do i need to change it to external domain as well?
thanks

Thanks mate,
I will keep you posted the outcome....
cheers