It sounds like you have the first generation of key fobs. I also had them and both stopped working after awhile. I also tried programming them with the ignition but to no avail. If the reprogramming doesn't work you may have to get new key fobs. The good news is that the new fobs are 2nd generation with the Gold Porsche crest. They are supposed to not be prone to failure like the earlier generation.
Sunset Porsche in Beaverton Oregon has the fob on sale for around $90. Make sure you take all of your keys to the dealer if you have to get them reprogramed. They will take the old metal blank and put it in the new fob. They will then program and verify that all keys work with your car.
Sunset Porsche charges one hour labor regardless of programming 1 key or multiple keys. Your dealer may or may not be the same.
I hope the at home ignition programming works for you!
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2000 2.7L Boxster, 21K
Litronics
Sport Package
5-speed
Rear speaker system
Harman Kardon Ipod system
Durametric software
OBC Hack
Triple Black
De-snorkled
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