Usually I do that first the night before. And no, I could not get the head on my floor pump to stay on after about 60psi. I tried a couple of alternatives, but decided I would get up in the middle of night to do further work.
But in the middle of the night/early-morning I met with no success either.
I switched the gasket thing with another identical model which had had an unfortunate break when I forgot to cross my thumbs. It seemed slighly better, but not significantly so. I had pumped up a few times through the fall. That corner of the basement gets pretty cool, so perhaps that finally wore out the sealing properties of the gasket.
Other pumps broken in various ways would not work themselves, and the gaskets, while almost identical in design, and in one case it seemed diameter, are not compatible between different makes.
One frame pump seemed like it would work, but would take a long time, and I didn't seem to have a gauge which would both register accurately and not let out a lot of air when used (I had been going by the gauge on my floor pump for several years). My trusty old 1980's Zefal HP seems to have acquired some internal problem which makes it very heavy to pump, although it did seem to be working (but see gauge problem). Usually it would be just tiresome, but had such a small body that it wasn't difficult to pump. But even when pumping without it attached to anything, there was a lot of resistance.
Often with a frame pump you get to just about 70psi so you can ride home. I actually never tried my active Silca, because I didn't want to waste its gasket life. And I had no working gauge, either.
So I was glad I'd set only a dry run as my target.
It was Sunday now, and my wife got up a little earlier than she'd said, and we'd done groceries the night before, so I got most of the afternoon alone while she went shopping.