So it looks like a lot of people are having this issue and seeing how Exchange 2013 is still new (relatively to the world) there isn't much data around to answer this. I've spend ALOT of time trying to figure this out.
Here is the answer. :) - No I don't know all but I'm going to try to give you the most reasonable answer to this issue, in a most logical way.
First thing I did when I was troubleshooting this issue is that I ignored Martina Miskovic's suggestion for Step4 http://technet.microsoft.com/library/jj218640(EXCHG.150)because it didn't make sense to me because I was trying to connect
Outlook not outside the LAN but actually inside. However, Martina's suggestion does fix the issue if it's applied in the correct context.
This is where the plot thickens (it's stew). She failed to mention that things like SSL (which I configure practically useless - anyone who ever worked in a business environment where the owner pretty much trusts anyone in the company, otherwise they don't
work there - very good business practice in my eyes btw, can confirm that...) are some sort of fetish with Microsoft lately. Exchange 2013 was no exception.
In exchange 2003, exchange 2007 and exchange 2010 - you could install it and then go to outlook and set it up. And when outlook manual Microsoft Exchange profile would ask you for server name, you would give it and give the name of the person who you setting
up - as long as machine is on the domain, not much more is needed. IT JUST WORKS! :) What a concept, if the person already on premises of the business - GIVE HIM ACCESS. I guess that was too logical for Microsoft. Now if you're off premises you can use things
like OutlookAnywhere - which I might add had their place under that scenario.
In Exchange 2013, the world changed. Ofcourse Microsoft doesn't feel like telling it in a plain english to people - I'm sure there is an article somewhere but I didn't find it. Exchange 2013 does not support direct configuration of Outlook like all of it's
previous versions. Did you jaw drop? Mine did when I realized it. So now when you are asked for your server name in manual outlook set up and you give it Exchange2013.yourdomain.local - it says cannot connect to it. This happens because ALL - INTERNAL AND
EXTERNAL connection are now handled via OutlookAnywhere. You can't even disable that feature and have it function the reasonable way.
So now the question still remains - how do you configure outlook. Well under server properties there is this nice section called Outlook anywhere. You have a chance to configure it's External and Internal address. This is another thing that should be logical
but it didn't work that way for me. When I configured the external address different from the internal - it didn't work. So I strongly suggest you get it working with the same internal address first and then ponder how you want to make it work for the outside
Now that you have this set up you have to go to virtual directories and configure the external and internal address there - this is actually what the Step 4 that Martina was refering to has you do.
Both external and internal address are now the same and you think you can configure your outlook manually - think again. One of the most lovely features of Outlook Anywhere, and the reason why I had never used it in the past is that it requires a TRUSTED
See so it's not that exchange 2013 requires a trusted certificate - it's that exchange 2013 lacks the feature that was there since Windows 2000 and Exchange 5.5.
So it's time for you to install an Active Direction Certificate Authority. Refer to this wonderful article for exact steps - http://careexchange.in/how-to-install-certificate-authority-on-windows-server-2012/
Now even after you do that - it won't work because you have to add the base private key certificate, which you can download now from your internal certsrv site, to Default Domain Policy (AND yes some people claim NEVER mess with the Default Domain Policy,
always make an addition one... it's up to you - I don't see direct harm if you know what you want to accomplish) see this: http://technet.microsoft.com/en-us/library/cc738131%28v=ws.10%29.aspx if you want to know exact steps.
This is the moment of ZEN! :) Do you feel the excitement? After all it is your first time. Before we get too excited lets first request and then install the certificate to actual Exchange via the gui and assign it to all the services you can (IIS, SMTP and
there is a 3rd - I forgot, but you get the idea).
Now go to your client machine where you have the outlook open, browse to your exchange server via https://exchang2013/ in IE and if you don't get any certificate errors - it's good. If you do run on hte client and the server: gpupdate /force This will refresh
the policy. Don't try to manually install the certificate from Exchange's website on the client. If you wanna do something manually to it to the base certificate from the private key but if you added it to the domain policy you shouldn't have to do it.
Basically the idea is to make sure you have CA and that CA allows you to browse to exchange and you get no cert error and you can look at the cert and see that's from a domain CA.
NOW, you can configure your outlook. EASY grasshoppa - not the manual way. WHY? Cause the automatic way will now work. :) Let it discover that exachange and populate it all - and tell you I'm happy! :)
Open Outlook - BOOM! It works... Was it as good for you as it was for me?
You may ask, why can't I just configure it by manual - you CAN. It's just a nightmare. Go ahead and open the settings of the account that got auto configed... How do you like that server name? It should read something like email@example.com
and if you go to advanced and then connection tab - you'll see Outlook Anywhere is checked as well. Look at the settings - there is the name of the server, FQDN I might add. It's there in 2 places and one has that Mtdd-something:Exchange2013.yourdomain.local.
So what is that GUID in the server name and where does it come from. It's the identity of the user's mailbox so for every user that setting will be different but you can figure it out via the console on the Exchange server itself - if you wish.
Also a note, if your SSL certs have any trouble - it will just act like outlook can't connect to the exchange server even though it just declines the connection cause the cert/cert authority is not trusted.
So in short Outlook Anywhere is EVERYWHERE! And it has barely any gui or config and you just supposed to magically know that kind of generic error messages mean what... Server names are now GUIDs of the firstname.lastname@example.org - THAT MAKES PERFECT
SENSE MICROSOFT! ...and you have to manage certs... and the only place where you gonna find the name of the server is inside the d*** Outlook Anywhere settings in the config tab, un it's own config button - CAN WE PUT THE CONFIG ANY FURTHER!
Frustrating beyond reason - that should be Exchange's new slogan...
Hope this will help people in the future and won't get delete because it's bad PR for Microsoft.
ALSO if you want to pick a fight with me about how SSL is more secure... I don't wanna hear it - go somewhere else...