Main won't drop on it's own

[Boatwright]

Are your halyards inside the mast? We struggled with our main a couple of years ago until I figured out that we had two lines twisted together inside.

[Smokeys Kitchen]

Originally Posted by BlackHeron

Make sure the mainsheet is eased and the vang is not pulling down on the boom. I've found that keeping the boom up so that it is less than a 90-degree angle using the topping lift helps keep the clew from pulling back on the slides and adding tension on them because of the boom dropping. Not having the outhaul super tight also helps at first too.

+1 here.

In our case the topping lift was lifted too much and created a binding on the slugs/track. We have a Tides Marine Strong Track - and it works very well. We just have to make sure all the things like boom vang, outhaul, and the topping lift are all squared away prior to dropping.

[AKA-None]

Originally Posted by Boatwright

Are your halyards inside the mast? We struggled with our main a couple of years ago until I figured out that we had two lines twisted together inside.

This also as I found mine wove between the bolts through the mast when I replaced the halyard

[Zoila DK]

Originally Posted by capt jgw

I have a stack pack on my main which makes it hard to reach the sail to pull it down as it's quite high. I tied the tail of the halyard to the bottom slide on the head board and use that as a downhaul. Sail goes up, the halyard tail goes with it. I can then pull it back down. And I don't have 50 feet of halyard to coil up either. After cleating off the halyard there's only a couple feet of slack that I just wrap around the winch. Halyard winches and cleats are on the mast, not run back to the cockpit. I don't think this system would work with that.

... you have a Stack Pack.
First I had nothing on my boom and the main sail got down with no problems.
Then I mounted a LazyJack, - and my main sail does not go down very well anymore.
When I take it down, it builds up a "stack" on top of the boom and at the end, there is no more weight to take the rest down.
I am not sure that is what your problem is, - but I have it right now and you might consider it.
My plan is to loosen my LazyJack so that the sail falls down a bit more to the side and see what that brings. Still, - annoying and I wonder how to fix it if that does not help. Anyway, - think about whether that could be your issue, - a stiff sail building up a "stack" going into the StackPack.