So the problem appears to be with file size. I can indeed upload smaller zip and image files, but I am unable to upload a 250mb zip file or mp4. Below are my php configs showing my size limit (1000M)
file_uploads = On
; Temporary directory for HTTP uploaded files (will use system default if not
; specified).
; http://php.net/upload-tmp-dir
;upload_tmp_dir =
; Maximum allowed size for uploaded files.
; http://php.net/upload-max-filesize
upload_max_filesize = 1000M
; Maximum number of files that can be uploaded via a single request
max_file_uploads = 20