Anyway: OS X 10.7.5 

Details: 

marduk:Vidalia nico$ uname -a Darwin marduk.local 11.4.2 Darwin Kernel Version 11.4.2: Thu Aug 23 16:25:48 PDT 2012; root:xnu-1699.32.7~1/RELEASE_X86_64 x86_64 

8 GB of RAM

2.9 Ghz Intel Core i7 

After installing the 14.3.5 update outlook mac refuses to connect to our Exchange 2010 mailserver, it first shows 'not connected', then tries to establish a connection, but I does not get any further then 'connecting', but the application does not seem to connect as the below netstat shows: 

marduk:$ netstat -p tcp 

Active Internet connections 

Proto Recv-Q Send-Q Local Address Foreign Address (state) 

tcp4 0 0 192.168.98.103.56349 247.32-78-194.ad.https SYN_SENT tcp4 0 0 192.168.98.103.56248 microsoft.iad.we.http ESTABLISHED 

tcp4 0 0 192.168.98.103.56212 lhr08s03-in-f7.1.http CLOSE_WAIT 

tcp4 0 0 192.168.98.103.55539 17.149.36.137.https ESTABLISHED 

tcp4 0 0 192.168.98.103.55063 st10402006.conne.https ESTABLISHED 

Outlook does not make any tcp/443 request to our mailserver, just nothing, a wireshark capture which I'm not going to post for obvious reasons, does not show anything happening towards our mailserver. I know that uninstalling - reboot - reinstalling will, most likely, fix this issue but I want to troubleshoot this, without going through the hassle (I have a 3 GB mailbox on our Exchange, I had to a complete resync multiple times (I'm not in the office much) so I wasted about 60 GB of data transfer meanwhile due to various problems with 14.3.2 where the only solution was when this 'connecting … and never connected' issue appears. 

Luckily as I'm installing exchange mailserver as of NT4, I'm in the position to troubleshoot the windows 2008 R2 server, Exchange 2010 (all updates, service packs etc installed) 

I have checked application and system log on the server, and nothing is pointing to the Exchange mailserver, nice and tidy logs, no issue whatsoever. 

Back to the client side, in my /var/log/system.log I have one entry, that refers to Office Mac: 

Jul 17 21:47:45 marduk [0x0-0x107107].com.microsoft.Outlook[5553]: objc[5553]: Class OnClickLinkAction is implemented in both /Applications/Microsoft Office 2011/Microsoft Outlook.app/Contents/MacOS/../../../Office/OutlookLegacy.framework/Versions/14/OutlookLegacy and /Applications/Microsoft Office 2011/Microsoft Outlook.app/Contents/MacOS/Microsoft Outlook. One of the two will be used. Which one is undefined. 

But I don't think it's related, correct me if I'm wrong. 

Standard logging (Window - Error log) does not show anything, after activating debug logs, followed by restarting outlook to generate logs, but even then: nothing, no errors. 

I think this is my first post on a public forum, I'm reluctant to open a PSS ticket for this (as most likely the result will be: reinstall) But I'm a bit fed up with the Microsoft triple R solution: Repair Reboot Reinstall, and the option Repair is not possible (manual download of this update shows that my current product is not fit for installation (most likely because the update is already installed) 

I can produce about whatever sort of logs, up to to deep analysis to reverse engineering to identify whatever system call, memory region etc etc etc, but that's one **** of a job, I paid nicely for this license which isn't exactly cheap and feel victimized by this vendor lockin, there is no alternative client with the same functionality (webdav / caldav is not supported) so per monopoly/patent war, I have to use outlook. 

So experts, give me you best shot. You guys have the source, I don't. 

You already lost me for the Windows client OS (gave up after Vista which costed me yet another 1500 Euro, the Vista capable story, replace laptop with a 'real' vista capable machine, sucked even more), bought my first macbook then, I like open source software but once again monopoly/patent war and business use, prevented me to continue using Debian as business environment. 

As a company, we have spoonfed Microsoft with several hundreds of thousand Euros. Finally, Office 2011 on mac is a resource hog, I can see my battery capacity going downhill as soon as I use anything (40% cpu load for an email client, come on) 

 Thanks n1c0n1c0