The case of the not updating Outlook for Mac 2011

exchange2007logo2[1]I had contact with a Twitter user on an issue with Outlook for Mac 2011 talking against Exchange Server 2007 on Small Business Server 2008.

When configuring a new account, Outlook for Mac reported “Account cannot be added.  Note that Outlook 2011 requires Exchange Server 2007 SP1 Update Rollup 4 or later.”

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However, that couldn’t be right because that user claimed to be running a higher version of Exchange 2007. After manually entering the server name, a connection could be established and an initial download of folders and contents took place. However, items weren’t updated and contacts and calendar remained empty.

After trying and checking some things, I asked to turn on Outlook for Mac’s logging hoping to find something in the Exchange Web Services log (Outlook for Mac 2011 is EWS based). You can enable logging by checking Window > Error Log > Errors > Settings > Turn on logging for troubleshooting. After a while I was sent the log file Microsoft Outlook_Troubleshooting_0.log which contained the following excerpt:

2013-01-24 08:55:34.392,0xFFFFFFFF,Outlook Exchange Web Services,Info,"EWS: Response data received on thread=0x7d27bdb4, XML data=
<?xml version=""1.0"" encoding=""utf-8""?><soap:Envelope xmlns:soap=""http://schemas.xmlsoap.org/soap/envelope/"" xmlns:xsi=""http://www.w3.org/2001/XMLSchema-instance"" xmlns:xsd=""http://www.w3.org/2001/XMLSchema""><soap:Header><t:ServerVersionInfo MajorVersion=""8"" MinorVersion=""3"" MajorBuildNumber=""297"" MinorBuildNumber=""0"" Version=""Exchange2007_SP1"" xmlns:t=""http://schemas.microsoft.com/exchange/services/2006/types"" /></soap:Header>

First, Exchange reports version 8.3.297.0 which corresponds with Exchange 2007 SP3 RU9 (EWS can report slightly different version than actual version), so something else was wrong while that’s well above Exchange 2007 SP1 RU4.

2013-01-24 08:55:39.355,0xFFFFFFFF,Outlook Exchange Web Services,Info,"EWS: Sending request on connection=0x7dc89be8, URL=/EWS/Exchange.asmx, SoapAction=""http://schemas.microsoft.com/exchange/services/2006/messages/SyncFolderItems"""
2013-01-24 08:55:39.358,0xFFFFFFFF,Outlook Exchange Web Services,Info,EWS: Received response on connection=0x7d31dae8; status=500
..
2013-01-24 08:55:49.861,0xFFFFFFFF,Outlook Exchange Web Services,Info,"EWS: Sending request on connection=0x7d71a648, URL=/EWS/Exchange.asmx, SoapAction=""http://schemas.microsoft.com/exchange/services/2006/messages/GetItem"""	
2013-01-24 08:55:49.863,0xFFFFFFFF,Outlook Exchange Web Services,Info,EWS: Received response on connection=0x7dc26638; status=500
..
2013-01-24 08:55:39.359,0xFFFFFFFF,Outlook Exchange Web Services,Info,"EWS: Sending request on connection=0x7d31dae8, URL=/EWS/Exchange.asmx, SoapAction=""http://schemas.microsoft.com/exchange/services/2006/messages/GetItem"""	
2013-01-24 08:55:39.477,0xFFFFFFFF,Outlook Exchange Web Services,Info,EWS: Received response on connection=0x7d7005c8; status=200

I then noticed various EWS requests returned http status code 200 (means OK) but also 500’s, which correspond to “Internal Server Error”. It happened after various requests (e.g. SyncFolderItems, GetFolder, GetItem) but not for all requests.

Now, code 500 isn’t very helpful (general terminal failure) and a quick restart of IIS with iisreset /restart /noforce didn’t solve things.

After some digging it turned out the seemingly unrelated KB2264110 pointed in the right direction. I say unrelated, because it’s on messages not being updated on Blackberry Internet Service (BIS) after installing Exchange Server 2007 SP2. Turned out the performance counters on the Exchange 2007 server were corrupt and rebuilding them solved the issue.

To rebuild the performance libraries, perform the following steps from an elevated command prompt:

  1. CD %SystemRoot%\System32
  2. Run lodctr /R (/R is case-sensitive) which will rebuild all known counters
  3. Run wmiadap /f which will update the WMI performance classes
  4. Restart the Exchange 2007 server

After these steps, Outlook for Mac 2011 could sync again with Exchange Server 2007 SP3.

Mac Outlook 2011 & Exchange 2003

There are still a lot of questions and tweets on Mac’s Outlook 2011, Exchange 2003 and why that combination doesn’t work. I can only assume people overlooked the system requirement in the Apple store, which clearly states “Exchange support in Outlook 2011 requires connectivity to Microsoft Exchange 2007 SP1 RU4 or later”.

The reason for lack of support lies in the fact that Outlook 2011 connects to Exchange Server using what is called Exchange Web Services. These services were introduced with Exchange 2007 (and thus are also available in Exchange 2010). The result is that Office 2011 can’t synchronize information, like e-mail, contacts and calendar, with Exchange 2003.

On a side note, you could use Entourage 2008 which utilizes the WebDAV protocol. This is supported by Exchange 2003 as well as 2007, but was discontinued in Exchange 2010.

Is this bad? I think not. Apart from the requirement, which is clearly mentioned, Exchange 2003 is almost 8 years old now. Products evolve and mainstream support has already ended for Exchange 2003. Even if Exchange 2003 is running rock solid, organizations should be considering on what to do with their Exchange 2003 environments as part of the IT life cycle management process.