The AWS Console simply does not support uploading large files to S3 Buckets. Thus you are forced to resort to an SDK or the CLI for large files. Bummer!

To install using Amazon docs is a long-winded affair. Here is the short version for OSX.

OSX ships with an outdated version of Python and AWS has a few dependencies such as PIP, and unless you are already a Python user and want to setup the environment manually, be my guest and take the long route using the AWS user guide.

If (like me) you could not care less about Python and PIP and whatnot… take these steps:

Create a new IAM User in the AWS Console. Give the user S3 Access Rights. Keep the window open you will need the access and secret key when configuring the AWS CLI.

Install and Configure AWS CLI

$ curl "https://s3.amazonaws.com/aws-cli/awscli-bundle.zip" -o "awscli-bundle.zip"
$ unzip awscli-bundle.zip
$ sudo ./awscli-bundle/install -i /usr/local/aws -b /usr/local/bin/aws
$ aws configure

Now go the the directory where the large file you want to upload resides.

Upload your huge file - in this case with public read access:

$ aws s3 cp my_huge_file.mp4 s3://bucketname/foldername/ --acl public-read