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Is there any way to tell Amazon S3 that all existing and future files in some bucket should have some speicific Expires header?

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You can always set policies for buckets, such that they will be applied to all objects added to it. You can use the AWS Policy Generator to create one -- though I'm not sure of the exact syntax for EXPIRES headers. If you find out the right format, please reply!

http://awspolicygen.s3.amazonaws.com/policygen.html

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