The switch may be on it's way out. That's the problem with the hydraulic switches. For the average switch, it needs a lot of pressure. There are low pressure switches on the market, so look for one of these. The solution is a mechanical switch. CASCO (and I assume the other Tbird parts suppliers) have a mechanical switch conversion that if adjusted correctly, lights the brake lights almost the instant you touch the brake pedal.
I put the CASCO unit on my 56. Been on the car s number of years with no problems.
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