Where were you --recursive when I was hacking around with for file * ; do aws s3 cp $file.....

$ aws s3 cp ./ s3://travisshears.images/image-service/images/oblastle/context/ --profile personal --recursive
upload: ./us-ak.jpg to s3://travisshears.images/image-service/images/oblastle/context/us-ak.jpg
upload: ./us-co.jpg to s3://travisshears.images/image-service/images/oblastle/context/us-co.jpg
upload: ./us-ar.jpg to s3://travisshears.images/image-service/images/oblastle/context/us-ar.jpg
upload: ./us-ca.jpg to s3://travisshears.images/image-service/images/oblastle/context/us-ca.jpg
upload: ./us-al.jpg to s3://travisshears.images/image-service/images/oblastle/context/us-al.jpg
upload: ./us-ct.jpg to s3://travisshears.images/image-service/images/oblastle/context/us-ct.jpg
...

--recursive is an easy win to upload a bunch of files to s3.