I did further testing. After removing the group condition, it still did not work. I put the group condition back in updated to 6.1 and it still would not work. I moved the group condition below the other conditions and it worked. It seems to be that if the group condition is the first in the tree the trigger fails, but works in any other configuration.
They were met according to my understanding of the logic system the triggers follow in the pcitures above. If I put the group back to its original location (first AND operator) it causes the trigger not to run. If I put Ticket Progress then Group, the trigger actions properly. I’m on the latest stable still as of last night (updated entire ubuntu server host and all packages). I’m betting it is something I have edited, but the only file I manually update is attachments.jst.eco to enable an HTML5 audio player for WAV and MP3 attachments (see my other posts).