*bump*
Hello. I'm having the same issue.
System info:
Windows XP
WLM 2008 (Build 8.5.1302.1018)
Plus! 4.82.0.368
Chat logging is basically working fine, but for only one contact it produces this problem. The HTML file is created at the beginning of the conversation, but it's empty, then it disappears when the conversation window is closed. The "basic" messenger log works fine.
If this helps: the contact blocked me for months, after a while I noticed that in the right-click menu the Plus! options went grey (so unusable) for them.
Any ideas what causes this?