@RBozeman I’ve managed to do it through excel manipulation, but it required quite some work. I had to basically map deals with associated contacts by id’s (vlookup) and then add association labels for each of these deal to contact associations (as I had the association label as a contact property). If a deal had multiple contacts, I had to break the id’s and association labels into different columns and import them in several batches to map each column deal to contact to assoc label.
I’ve tried with Insycle (free trial) but for some reason it didn’t want to work, I couldn’t select the proper functions or fields in the association bulk operations. If you want we can try a screen share sometime to show you the issues I ran into (macos, chrome).