(Alert: I posted this same topic on Standup Zone, the US based site, so I apologize if you come across it twice. I am guessing that there are a lot of great Aussie surfers who may not track that site, and I did not want to miss their input.)

This summer I have been working on what I think of as the three different paddle technique options during frontside cutbacks:
1. Doing a hard sweep with the paddle on the toeside to help the board turn into the cutback. In this technique, the paddle is being used as a turning force to help push the board around, or even to pull against to break the fins free.
2. Skim the paddle lightly back along the top of the lip at the start of the cutback until it is directly behind you so that you can basically sit on it during the latter phases of the cutback to get more body angle on the heel rail. In this case the paddle is not being used as a turning force, but as something to lean on in order to get more leverage on the heel rail during the later portion of the turn as you are coming back towards the whitewater. Colin McPhillips is my favorite image for this move: I love the way that he uses the paddle to help carve the heel rail around the cutback, rather than the technique so many people use to just pry the board around with the paddle.
3. The cross-bow paddle move, in which the paddle is passed over to the heel side of the board to act as a center pivot for the turn.

For various reasons, the variation that I am working on the most right now is #2. But here is the problem I am starting to run into.
As the carve starts, I sweep the paddle back along the surface of the lip with the convex surface of the blade along the water so that it planes, and then once it is behind my hips, I lean or almost sit against the paddle so that I can lean harder on my heel rail during the last half of the turn as I am coming back towards the curl. So far so good, but at least half the time I come out of this move with my paddle blade caught in the loop of my leash which totally messes up my ability to lean out on my paddle on the toe side as I rebound off the whitewater. Yesterday this happened five out of six waves in a row; drove me crazy. A lot of the time, Colin who is the master of this move, is not using a leash, so I cannot see in the videos how he would deal with it.

Does anyone have any insights on how to avoid this problem?

Yes shorter leash could help although I went for a 7' leash recently, which was fantastic for quick board retrieval after wipe outs but regularly gets wrapped around the fins when paddling which is a nightmare! Obijohn, i think its a combo of technique #1 and 2 you want, 3# no go as takes to long/upsets the carve and is not neccessary unless you're going into more of a roundy. I've found the best web resource for short SUP technique is "Paddlewoo". Eric is a powerful concoction of passion, techincal expertise, inquiring mind and quite frankly inspiration.

Colin seems to wear a leash in the vid.

I use a 6' leash, even on 7'6" boards. I even used 5' leashes on my 6'8" at some point. But it never wrapped in the fins.
Perhaps you may want to stretch it a bit (warming it with hot tap water?) to get rid of the "folds" in new leashes?