Oh my gosh!!! I'm having the same problem with the toes on my right foot, and I'm wearing Specialized Taho MTBs. The first pair was a womens' WSD so I returned them for the men's version in a size larger -- same problem. I can't believe this thread describes my problem to a T !!!

For me, the numbness and pain begin around mile 15. It gets worse and worse until my foot feels like I have a tight wire band wound around all the toes on my right foot and getting tighter. We finally stop so I can remove the shoe and massage my toes.

I thought the problem might be that my 2nd toe is longer than the big toe, or maybe I'm curling my toes inside the shoe. I've even considered having surgery on the 2nd toe to shorten it -- how desperate is that!!!!

I'm replacing the Tahos with a pair of Sidi Dominators. Meanwhile, I am wearing my old running shoes which feel as comfortable as slippers on my feet. The Sidis feel the same. Even in the running shoes, I can feel my toes scrunched while I'm pedaling, so I must be doing something I'm unaware of. I need to work on keeping my toes flat and spread out, not scrunching them up inside the shoe. However, I can ride for many miles in the running shoes without the pain I had in the Tahos. Otherwise, I liked those shoes... nice looking and durable.

I also wear orthotics, but the pain is there whether I wear them or not.