Sounds like one of the older Rem triggers. They had mucho problems. Call Remington and get a new trigger.
Did you cock the rifle before trying to engage the safety?( I ask because some are not familiar with firing pin block safeties as they are with trigger mounted safeties) If you did, and it still doesn't work, you need to find a pro who is familiar with 3 position, swing safeties. The Win. is much more 'involved' than the aftermarket models made for Mausers, Springfields, and the rem 700s. Another thing to consider, Pre 64 parts are scarce. Mess it up, and it can really get expensive! Post 64 parts aren't gonna' fit/work.
Hay Bowhunter#18, "please" clarify what make, model and year of rifle you are referring to by " Pre64".
How is this helpful?You need to send it to Remington or
Most likely someone has tinkered with the trigger and the safety will not engage because the firing pin and sear is out of adj the safety moves the firing pin back some when engaged probally a simple fix a gunsmith can fix it in a heartbeat while he's working on it get him too put a lighter trigger spring in if it hasn't all ready been done pre 64 triggers are great but with the factory spring there pretty hard a lighter spring will do wonders on that trigger good luckI tried all of the easy fixes and I am not that lucky. I need some one that has worked on safety after removing it. I am sure it is going to take some fine file work to take a burr or flat spot off. Hoping one these Winchester pre64 guys will send me a video. Eric 904-449-3066