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Gateway endpoints (S3, DynamoDB) cannot be extended outside of a VPC (https://docs.aws.amazon.com/vpc/latest/userguide/vpce-gateway.html#vpc-endpoints-limitations ).
We used to publish a design pattern that talks about using an ASG fleet of proxy servers inside the VPC to provide this connectivity, however the blog post has been removed, and the only link I can find is this one: https://d0.awsstatic.com/aws-answers/Accessing_VPC_Endpoints_from_Remote_Networks.pdf
The design pattern works and is used by lots of customers, but obviously has additional service / management costs to consider.
