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When in doubt, tape it off. Seems like you'd have to take off the interior paneling though to get to it
 

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Dont do any of the above lol...its easy...

Just open your door, push the weather stripping aside where the insert sits, and voila...two screws which hold it in place. Then just lift it out and paint it.
 

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The plastic part is called a Sail and it comes off very easy. Pry out the window weather strip and pull it up and out of the door, only a short piece extends into the door. On the outside of the door frame behind the Sail there are several screws under the exterior weather strip. Remove the screws and slide the Sail up and out.
 

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hahaha...yes, this is true...

i may have forgotten a key step, there...

roll window down ;)
then push the weather stripping aside
unscrew
remove
paint
reinstall
The screws on the outer door frame have to be remove, I believe the inner screws can stay in place.
 
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