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My guess is that belt is rubbing on the edge of the flat pulley which is the spring tensioned one. Either upon entry onto the pulley , or when exiting the pulley. some tweaking on the arm the pulley is attached to may fix it.
I had trouble with my belt coming off last year. Played with different belt lengths and tweaking things and got it working good. Belt has not come off since. Can’t remember the belt length I finally used for sure, but I think 81”. Blue belt like the one in your picture, and it would be 1/2” belt. Just bought it a box store. Second season for it. Was use a lot the first season, only used three times or so this season so far. But still works good. Doesn’t come off.

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