Cannot connect Surface Pro 2 (Windows 8) to SBS2011 Exchange server using Outllook 2013

The built in win8 mail cloent, android, and iOS, all use exchange activesync. A protocol heavily optimized for mobile devices. Outlook 2007, 2010, and 2013, on the other hand, use Outlook Anywhere, which is a different protocol. So yes, it is entirely possible for one to work and have the other fail.

Start by testing your server for Outlook Anywhere problems. Www.testexchangeconnectivity.com has tests for just that sort of thing. Knowing what the error is a necessary first step towards fixing it.

Outlook 10 connects fine. But I will run thru the testing site.

Outlook 2010 on a local LAN still defaults to MAPI. 2013 now uses OA whether remote OR local. That was a significant change in 2013 and is documented in the release notes.  OA *must* work for 2013 to work where it could be broken and 2010 and EAS clients would work okay... never indicating that OA was broken.

OWA Works from the system.  RWW Does not but I will set to compatibility mode and try again. Thank you.

Auto discover Failed, But Manually setting server worked. Which (to me) explains why I can connect remotely with 2010 and not 2013, because 2010 lets me define the server/domain/etc. and 2013 does not.

Auto-discover errors:


      Testing RPC/HTTP connectivity.
       The RPC/HTTP test failed.
       
      Additional Details
       
Elapsed Time: 946 ms.
       
      Test Steps
       
      The Microsoft Connectivity Analyzer is attempting to test Autodiscover for auditor@xxxxxxx.com.
       Testing Autodiscover failed.
       
      Additional Details
       
Elapsed Time: 945 ms.
       
      Test Steps
       
      Attempting each method of contacting the Autodiscover service.
       The Autodiscover service couldn't be contacted successfully by any method.
       
      Additional Details
       
      Test Steps

How do I setup a DNS entry for auto-discover?

Tried:

1) Set compatibility mode for remote.xxxxxxx.com
2) Login to RWW (Successfully)
3) Download sbs Certficate
4) Install 3rd Party Certificate (Go Daddy)
5) Attempt to login thru outlook, Error:

Cannot Start Microsoft Outlook. Cannot open the Outlook window. The set of folders cannot be opened. The file C;|Users\xxxxx_000\AppData\Local\Microsoft\Outlook\XXXXXXX.ost is not an Outlook file (.ost).

I press OK, then get:

The connection to Microsoft Exchange is Unavailable. Outlook must be online or connected to complete this action.

At this point I think I need a DNS entry for auto-discover. Any advice would be appreciated.

Also, I verified that Autodiscover is enabled in SBS2011.

I have found this article: http://www.thirdtier.net/2009/02/setting-up-an-external-autodiscover-record-for-sbs-2008/

Highlight:
The details on how to set this record up are all in KB940881, but I’ll briefly summarize it here:

1. Get rid of any CNAME or A records for “autodiscover”, and any wildcard “*” records in the public DNS zone. This is a critical step, so don’t just drift past it.
2. Build the SRV record to look like this:

Service: _autodiscover
Protocol: _tcp
Port Number: 443
Host: remote.smallbizco.net

Will this solve my problem?

You are doing this inside the sbs domain?
Or from a remote location?
If you are doing this remotely you need to try again with an active VPN. (Need to allow VPN connections on the SBS box)
Also need to manually add the dns suffix for your sbs domain and add your sbs server IP as primary DNS.
Run a manual setup only (use a new profile).
Also make sure the SBS has the latest rollup installed. (Or at least rollup 3)
Let me know.
Olaf
I does work so don't give up.

From a remote location. The goal was not to need a VPN. I thought (I could be totally wrong) that Outlook Anywhere did not require a VPN.

Added DNS record:

Service: _autodiscover
Protocol: _tcp
Port Number: 443
Host: remote.xxxxxxx.com

And Remote connectivity analyzer test worked for Outlook Anywhere (RPC over HTTP). Now to create new profile and try again.

It only needs VPN for the initial setup I have found.
You can turn  it off after that.
Olaf

Created a new (Test) account on Surface to start from scratch.

1) Add xxxxxxx.com to trusted sites
2) Set to compatibility mode for remote.xxxxxxx.com
3) Installed the SBS certificate
4) Installed 3rd Party (Go Daddy) certificate
5) Ran Outlook (Manual Setup)
6) Checked Connect to Microsoft Exchange using HTTP (Under Outlook anywhere)
7) Set proxy server to https://remote.xxxxxxx.com

Got a new message - "You must restart Outlook" Then got a Windows Security pop-up asking for credentials.

8) set to xx\user to change domain.
9) After restarting Outlook, it asks me for my credentials.
10) Restarted system and tried to load using the newly created test user account

Get: "The connection to Microsoft exchange is unavailable"

IT seems like Im making progress...  ...but very frustrating.

When I try to to open Mail (From control Pannel) to delete/create new profile, I get:

Windows host process (Rundll32) has stopped working.

Run a repair on outlook.
Delete all Exchange profiles before doing so.  You'll have to create a generic pop account as default profile in order to delete the exchange account.
Rin Ipconfig /flushdns before running the  VPN and starting again. Add your RPC details manually and do NOT use offline settings (cashed) for now.
Olaf

@ Olafdc - I have not accessed thru VPN before. How do I set that up to test?

Added a pop account, still cant open the mail icon to delete the other profiles. How can i get the exchange profiles deleted? After closing/opening Outlook it goes back to trying to load the exchange account.  

I am still not sure how to start/run the VPN.  Thank you for your patience.

About to reset the surface again...

Is there any difference between office 2013 preloaded on the surface and what I would download from the Microsoft site?

If I reset the surface and start all over again what would the basic steps be to get connected.

How do I start the VPN before connecting to Outlook

Good idea: Reset surface and start again. (they act like toys, not computers fromtime to time)
Server: SBS console>Network> Connectivity>Configure a VPN>Allow users to connect to the server by using a VPN>Finish wizard.
+ Forward port 1723 to your server IP from your firewall.
SBS console>Users and Groups>choose your account>Edit user account>Remote Access> Tick the box next to: User can access VPN> OK

On workstation:
Controlpanel>All control panel Items>Network and Sharing Center>Set Up a new connection or network>Connect to a workplace>Next>Create a new one.next> choose your existing internet connection (VPN)>Use "remote.xxx.xx" for Internet address> Create
Click on connection to connect.
Hope that helps,
Olaf

Thank you for posting I will try that and update

Setup VPN/Outlook as above, got connected just fine. Does the VPN have to be connected from now on?

Thank you!

I referred back to your prior comment about only needing VPN for initial setup.  Thank you for working through this with me. You were very clear in your instructions.

Glad you got it going.
Olaf