96 Grand Caravan Transmission Question

OK I replaced the Front pump seal, O-ring on front pump and Front pump gasket. How can I get the Front pump back in without destroying the new O-Ring seal? The pump goes on then seems to get stuck / stop just as the O-Ring is in contact with the Transmission. I dont want to force it because Im afraid it will just destroy the o-ring. OR, am I doing something wrong and missing something?

3.3 V-6