Originally Posted by toxictv
My '02 Sahara is a little notchy going in to second and third if I force it, but if I wait a second it falls in to place. I'm sure it could use a fluid change, and that's what I'd recommend for you to try first.
I shift my TJ's trans like a truck driver not like a sports car and it eases into each gear w/o grinding. If you force it past the syncros constantly the trans will fail sooner than later.
Colder weather makes the fluid thicker and the syncros rotate slower taking it a little longer to line up the gears. Changing the oil will help some but just be patient.