I’m running Outlook 14.3.6 on OS 10.8.4 with SpamSieve 2.9.7
On about half the messages in my inbox that have not been flagged as spam, I hit the hot-key for the “Train as Spam” script and Outlook immediately goes into “not responding” mode, using 100% of a CPU. Quitting SpamSieve has no effect. I have to Force Quit Outlook.
I sampled the process when it hung and attached it to this post.
How long did you let it run before force-quitting? It looks like Outlook is hard at work generating the source for one or more HTML e-mails. Perhaps there’s a particular one that it’s getting stuck on.
I let it run for a minute or two
From the looks of the sample, it might work if you let it run for longer. However, I would suggest training one message at a time to try to see whether there’s a particular one that’s triggering the problem.