I have this pump here: Bike Parts - Specialized
It’s in practically new condition.
I should clarify that I have the most trouble trying to attach the chuck, and keep it attached, when connecting to a completely flat tire. Half of the problem seems to revolve around the way the entire stem wants to disappear into the rim and tire while I’m trying to attach the chuck. With a completely flat tire, I simply can’t get the chuck to grab enough of the stem to get a grip. Maybe I can “fix” this by finding tubes with the longer stems.
I also have an odd issue wherein, even if I do get a solid connection, I encounter a ridiculous amount of resistance when I try to pump the air into the tire. Even when the tire is completely flat and there should be no back-pressure. I have no idea what could be causing it, and had the same issue with my previous pump and multiple tubes. But it doesn’t happen every time, and I can’t spot any pattern to what’s causing it. Sealant in the tube? (We have a lot of goatheads around here, so it’s sensible to run thorn-resistant tubes with sealant.)