I found that my shoes clicked into place much easier if I twisted my heel slightly to the outside as I pushed in. But I have turned-out feet and my natural position is with heels inward as far was the cleat will allow. My cleats have developed some fore-aft play which I find disconcerting, but the little hex screws that are supposed to adjust that are frozen. And the cleats are only 4 months old.
Oil is good, grease is better.
2007 Peter Mooney w/S&S couplers/Terry Butterfly
1993 Bridgestone MB-3/Avocet O2 Air 40W
1980 Columbus Frame with 1970 Campy parts
1954 Raleigh 3-speed/Brooks B72