The tool does not stop just loses power and no the compressor does not kick in at that point. I will try some of the recommendations Thanks

That's your best answer there.
Do some basic diagnostics. Are there any valves or devices between the tank and the tool that could be cause a flow problem (it sounds like a flow problem to me). What is the condition of the hose (kinks, collapsed places, car parked on the hose, leaks, etc). Eliminate every variable - meaning valves, hoses, devices - you can, one at a time, working your way back to the tank, to see if there is a difference.

Change out the basics first:
The cheap fitting ends have a ball valve in them which may be stuck.
(Probably not though)

The compressor not kicking with low pressure probably means a bad regulator.
(or just the setting)

The crazy me would suggest bleeding down the tank and spraying some carb cleaner into the intake and running it through.
Follow that soon after with some cleaner/lube like Marvelous Mystery Oil.
Follow that with pure gear oil or compressor oil something.

The system will be contaminated with oil and can't be used for spray painting anytime soon.

One other thing on moisture in the system. If you're using a hose reel, extend the air house out all the way, put a blow valve on the end and run the air to make sure you have any moisture out of the lines. Springtime when we're going through warm/cold/warm cycles can cause condensation in the airlines that gets trapped. As it builds up it comes out in slugs that will make an air tool bog and lose power.

Is your shop heated all the time or at all?

Look at your quick connects. Switch to a highflow one like a Milton V. Quick connects are very restrictive.

I actually do use the Milton ones. I tried the HF ones and they leaked and worked like crap.
Update on progress I went to drain the tank and the valve is broken so I am waiting for a new valve to arrive so at a standstill until it arrives.
Thanks for all of the replies and suggestions I will update my findings when the new vave arrives and I do the rest of the checks suggested

Alternatively....for the layman

When I burp my impact wrench I can hear my 50' rubber hose filling back up because it "deflates". I hear the air passing through the regulator into the hose as the hose equalizes with the tank.

It takes about a second to refill. Yours should be about the same.

I suspect the compressor is about 20+ years old based on the model # search. Also oiless? I've never had one last that long.

That would indicate that you've been emptying the condensation from your tank far too frequently! :D