For the longest time I have lamented my difficulties pumping up my bike tires. Especially with the floor pump. I don't expect as much for the on-the-road hand pump. (although it does pretty well) A little bit of trouble attaching pump to valve stem. More trouble getting it off. The feeling that pumping up the bike tires is more exercise than riding the bike to work. And the frequency of getting a flat the day I do a maintenance pump up.
Then it got worse. There was a terrible sound of escaping air every time I tried to pump up - and it wasn't the valve connection. And pump as I might, hardly any increase of tire pressure. Something was wrong, you think? I never even thought about the PUMP having a leak. Until it was quite obvious. I have no idea how old the bike pump was. My ex bought it back in the days of his bicycle commuting which he gave up (after a couple of bike vs vehicle encounters) years before we split. The pump was old. Way too old.
So, I finally bought a new bike pump. WOW. The old pump had a gauge with a moveable marker so you could set your goal pressure and see when you achieved it. The new pump does not, but the gauge is at the top of the pump instead of the bottom so it is easier to see. I don't know why the difference, but the new pump is easier to connect/disconnect. I have done several pump ups and so far (knock on wood) not destroyed my valve stem. Of course, also now I try to PUSH the pump off the valve instead of pulling it. And it is amazing how much easier it is to pump up the tire when all the air actually goes into the tire.
Sometimes in life we overlook the simplest and best answers.