Well met G2, greetings from Canada
Did you do anything wrong? Not really; you trusted the Dealer to set up the boat for you, and in all honesty he probably did.
Yet a furling Mast takes practice to make sure that you understand exactly how it works: For one, the Downhaul for the sail must be very tight or the furling gear can't do it's job. As the lock for that line is not spring loaded (as a camlock), simple transport or mounting the mast in it's collar can cause the downhaul line to slip out of its fitting).
The line spool around your mast must be filled with furling line when you have finished pulling out your sail. This is almost like 'stored energy'.
This allows you to pull on your furling line and retract your sail around the mast every time without question. (This is also so important as you learn to how much sail you need to expose to the wind with your furling system).
It's just a part of the learning process. This is a simple boat (yet the instructions have to be followed to the letter). I truly wish Hobie would loose the photo copies in Black and White and produce a Pro Video on how to set up any of their boats.
Hints: Vid Cam artists out there, do a demo and send it in to Hobie
Looking forward to hearing more about your Adventures on your TI,
(the

was because I had the very same problem the first time I took out my AI...)
Best Regards
Trinomite