odd that 3 inflators are all bad. maybe the tire stem is frozen. at least in a warm/quiet place you could inspect the tire better
I think after 22 posts on getting a tire fixed, we might be over-doing it a little.
A friend that owned a tire shop told me to always push the valve in for a second or two in Minnesota after putting air in the tire, especially in winter. Forces any water or ice out of the valve so it won’t leak. I’ve been doing it for years.