1. Deburr and slightly radius/chamfer the holes with a rat-tail file, diamond ball burr, ball hone, etc
2. Apply silicone grease for assembly. Diver’s (SCUBA) grease or just automotive dielectric grease. For stubborn applications or things like a valve where it has to slide a long distance, lube both the O-ring and the tube. For example, my usual approach for installing a valve is to use a foam mop to apply a very thin film of silicone _oil_ (30W) to the tube and a little silicone grease on the valve O-ring and perimeter.
3. If the O-ring is still getting cut, use a blunt object to press down the O-ring while gently advancing it past whatever hole is cutting it.
And a couple of things that are obvious but are sometimes easy to take for granted:
4. Use the correct size O-ring. There are a lot of places where a dash size (imperial) can be used in place of a metric, and vice-versa…but sometimes the slight difference is just enough to make one more apt to getting cut.
5. Use the correct durometer. A high durometer (hard) O-ring is more likely to get cut on installation. 70 durometer is good for most AG applications if a particular durometer is not specified. 90 is good if you can get it installed. 50 is generally too soft for high pressure applications because it may extrude into the gap and fail.