If you look at the top of your mast, you should see a little Y shaped piece of metal on the front. The "stops" on the halyard get pulled up and over and then latch into the Y hook from the bottom, which is what prevents your halyard (and sails) from coming down. The cleat on the bottom of the mast is just to hold the extra line, it isn't meant to actually hold any weight.
My boat is a little newer, and only has 1 stop, I believe the older ones had the extra one for reefing your sails.
They should not prevent you from raising the halyard, but they can be a little tricky to get set all the way in. You can try running the halyard all the way up and down with your mast down just to make sure it isn't sticking somewhere, but it definitely took a fair bit more effort to get that last bit of sail up than I was expecting when I first raised my main. Might help to lube your sail track up a bit as well. I would bet that is what is sticking, not the halyard.
One thing that seems to help, I try stepping away from the mast towards the front of the hulls a little when raising the last few feet so the stop doesn't catch in the hook on the way down, then once I know I have it raised all the way, I step forward and lock the stop in place. Then I yank the sail/boom downward (while holding the halyard, just in case) and make sure it is locked in at the top.
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