I use something like this in my app.yaml:
- url: /images/[0-9]*/(.*\.(jpg|png))
static_files: static/images/current/\1
upload: static/images/current/(.*\.(jpg|png))
This matches /images/[any number]/something.jpg to
static/images/current/something.jpg
Then in my templates I substitute the [any number] part for the apps current
version number ( os.environ.get('CURRENT_VERSION_ID', '0').split('.')[0] ).
So if I change my version number everything is re-cached.
You can also just append a query parameter to files to defeat caching. (
'/images/current/something.jpg?v=1' )
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