Friday, 23 April 2010

image I’ve been fighting a bit with my installation of Outlook 2010 (beta) for the past several days. Don’t get me wrong, now: I love Outlook 2010, it’s by far the best version of Outlook ever. The ability to have multiple Exchange account visible at one time is a killer new feature, and there are a lot of other great improvements.

But Outlook can be challenging sometimes. It’s a complicated program, especially when used with Exchange. So. now was just one of those times. Consistently the program would hang and I’d have to wait for what seemed like an eternity for it to come back to a responsive state. I did a lot of analysis and narroowing down the behavior by disabling a lot of account and feature settings, and decided that it seemed to be related to a hosted Exchange account I use for my email service. The more account features I enabled and accessed in Outlook, the more it would hang. For example, if I accessed the calendar associated with that account and then tried to open something, or if I switched from the calendar back to the mail view, or if I tried to look up a contact, Outlook would hang. It was to the point of being ridiculous in terms of getting anything done, since the hangs could last a few minutes or more at times. Outlook actually trained me to walk away and come back in 5 minutes. But that’s better than a busted up laptop, I suppose!

I started troubleshooting this and a couple other issues I was seeing that were affecting performance. One of the problems with trying to resolve Outlook issues is that the error messages the program provides are often very generic in nature and don’t point to a root cause. If I had a dime for every time it told me I didn’t have permission to do something , or for every time Outlook told me it’s trying to connect to an Exchange server and failing, I’d be rich. There are a zillion things that can cause these generic, simple errors. And the funny thing is, sometimes it’s not even an Exchange server it’s connecting to, even though it says it is. It might be connecting to a domain controller name instead to try to go a GC lookup, for example. You have to know what to look for, and how Exchange and Outlook work, in order to solve most Outlook behavior issues. Luckily I have a lot of past experience in that department.

At any rate, I eventually got to the point where I was spending my time looking at the Exchange Server’s connection status window. To see that, you locate the Outlook status icon down in the task bar near the clock, hold down the CTRL key, and click on the icon. Then you can choose the menu option for Connection Status. You only see that option if you CTRL-click the icon, though.

         (Server names omitted where appropriate to protect the innocent)

One of the first things I noticed was the fact that there were communication failures to my hosted Exchange server see the red-outlined numbers above), and that the connections were taking a long time to establish themselves. The status would stay at “connecting” frequently, and that was always the same time when Outlook was hanging. So, I figured was getting somewhere. At least I had a likely correlation. The other Exchange server, which is domain-authenticated and available on the local network, wasn’t hanging. Connections were quick and reliable (as you can see from the numbers above) on that one.

That made me think some more. Every time I start Outlook, I am prompted to enter my credentials for the Exchange Server. Despite the fact that I click the “save password” box when I log in, I am always prompted when starting Outlook. I had planned to see if there was a certificate mismatch problem of some sort, but with the connecting communication failures happening, I wondered if there might be a problem with the credential being passed to the server. As you can see in the connection status windows picture, the connection is an Outlook RPC over HTTPS type, and so I went investigating in the account settings for the account:



Sure enough, I found what I suspected I might: Outlook was prompting me to enter a username and password – behavior that’s associated with basic authentication – but Outlook was configured to use NTLM authentication when connecting. So, logic says that it was trying for a NTLM auth, waiting around for it to time out, and then reverting to the lower-security username and password over HTTPS. That would probably explain the communication hangs, and why Outlook wasn’t saving the plain text credentials when I asked it to.

I changed the proxy authentication setting to use basic authentication, and restarted Outlook. I was prompted to enter my credentials once, and haven’t been asked since. And, the connection to the server is much more snappy and reliable.

I don’t really know why the communication hangs started up a few days ago. Perhaps something changed settings-wise when my svchost.exe file got eaten by my AV software. I have been running Outlook 10 beta for a couple months and it was a new issue (although the credentials pop-up was consistent since installation).

But, regardless it looks like at least one or two of the problems I was having are now solved. And that’s a good thing. Now I’m off to troubleshoot some auto-archiving issues.

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Microsoft Office | Tech
Friday, 23 April 2010 17:07:55 (Pacific Standard Time, UTC-08:00)
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Sunday, 25 April 2010 13:50:40 (Pacific Standard Time, UTC-08:00)
Hi Greg, Thanks for sharing this as I too have had similar problems. My 2010 was also on the NTLM setting, I have changed it so lets see if that will work for me also.
When you crack Auto archiving let us know as its driving me crazy saying its doing it but then not actually doing it at all!
All the best, George.
Monday, 21 June 2010 04:07:52 (Pacific Standard Time, UTC-08:00)
I experience similar connection issues / hangs with Outlook 2010. Often the simple inclusion of a signature in an e-mail would hang Outlook, apparently because it had to retrieve that signature from the server.

I've just changed authentication method to Basic Authentication, so let's see what happens. Communication fail count still at zero, which looks promising.

By the way: great tip about that Connection Status screen. Didn't know about it!
Monday, 27 September 2010 10:11:46 (Pacific Standard Time, UTC-08:00)
I too have similar issue. I change the authentication method to basic and it works great for a day or two, then it reverts back to NTLM. I am getting tired of having to change this back all the time. Any ideas?
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