Welcome!
Quick search on google with keywords "boxster 986 spoiler problem one side" returned possible misalignment, loose connections, pressure on the switch causing one side to come free, intermittent contact, etc. (renntech.org)
Guessing you'll first need to remove the rear bumper to have a good visual of what is causing this. If I am correct I think there is a youtube HowTo remove the bumpers on this car.
Luck mate
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'97 Boxster base model 2.5L, Guards Red/Tan leather, with a new but old Alpine am/fm radio.
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