OK, got it again. I looked at the log for pings, and they were fine. However, XML sitemap did not finish. I clicked around a bit more, and saw nothing unusual.
What was odd is the error messages said how much memory the plugin tried to use, and how long the process took. Neither values exceeded my limits. Maybe something in the plugin "stack" took too long prior to the sitemap plugin firing, but I'm at a loss what it could be.
I think the best way to debug the issue was copy and send the error information to the XML sitemap folks to see what they can suggest.