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Thanks to everyone for all the replies and info, we ended up getting a well guy to come out. He replaced the check valve at the pump and so far it is now holding pressure. His take on it was to try...

The new tank is in the house about 5 ft of pipe from the switch.

The pressure switch is under the house from the original install, never been touched.

Sounds like the possibilities are the in ground pressure tank bad or a leak somewhere. After reading some...

So, if I understand correctly the pitless adapters connection could fail over time essentially creating a leak which allows the pressure drop. I wonder if we could detect the leak by looking down the...

We did not remove anything at the well head. I am not familiar with the "AW8A" is that a valve of some sort?

That would not suprise me at all, I was not there when the well was drilled but I would guess they buried it to keep it from freezing? or maybe the well guy was planning to replace it about now....

That we have to dig out the old presure tank and cap the connection since we now have a new tank in the house. How likely is it that the old tank still has enough air in it to be causing the 5 minute...

The well was 155 ft deep from what everyone remembers.

We have a vacation cabin in the Southern tier of NYS. The well was put in about 12 years ago with the presure tank (thought to be a membrane type)buried 6 ft deep next to the well head. The issue was...