Hi Fred, You might be able to beef up the condition editor by instead putting the smarts into the attributes you use in your condition. E.g. have an attribute that checks if an attachment exists yet with a creation date/time >= creation date/time of the work item.
If that's still not enough you might need to resort to the workflow step programming exit in the miscellaneous section... that is really getting into advanced territory.... & you might want to have a look at MDG at that point.
Just a thought
Jocelyn