I have one of the "standing" pumps with the double-ended attachment that will, ostensibly, do schrader or presta, the bike originally came with dunlops that the pump had no issues with using the presta side, but my rear wheel has had two punctures and two replacements since then. The first replacement was a presta that was really long and that worked fine but the second is a bit shorter and it doesn't seem that the pump will engage it(yes I unscrewed it and got a scoot of air by depressing the valve core before attaching the pump), a couple of quick pumps has it reading 100+ psi on a still squidgy tire so it's evidently just "inflating" its own air hose. What's bizarre is that the newer presta isn't noticeably shorter than the dunlop that's still on the front tyre and I can inflate that no trouble.
I have a dinky hand pump that works but I haven't been able to push the tyre above 50psi(ever polite bike shop recommended that "a big lad" should go for 60ish :P ) without feeling like I'm going to snap the valve off. Is there something I might be doing wrong that I can fix, or am I going to have to get a different pump/inner tube?