Originally Posted by
joeangelo
I have never been able to clip the shoe in by hand while off the bike; I always had to be on the bike pushing off in order to clip in.
Even if you can't get it to engage that way, you should be able to see what the issue is. Try putting the tip of the cleat in and, while holding the shoe against the pedal, rotate the pedal and try to look from all angles. Also, cycle the retention mechanism on the pedal to make sure it is free.