Why is inflating a Presta valve on a bike tire so finnicky?

I feel like me and Presta just don't get along! A lot of times I place the chuck on, it does not engage in order to pump in air. Or, if it does, then when I remove the chuck from the valve after inflating, a bunch of air is released from the tire.

HOWEVER: if I just use a little Presta to Schrader adapter and use a Schrader chuck to inflate the tire instead, it works much better. I can pop off the Schrader chuck instantly, with no air loss. Then, just unscrew the little adapter from the valve.

It doesn't even matter the pump or compressor being used, it just always seems to work more reliably if I attach to the Presta valve using Schrader instead of trying to pump using Presta directly.

Has anyone else experienced this with Presta valves?