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.”

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.