I have created a PIL Image and I want to send it to a server over requests. My code looks like this, but I am not able to get it working as I get no errors. import requests from PIL import Image from io import BytesIO img = Image.new('RGB', (25, 25), color = (120, 120, 20)) byte_io = BytesIO() img.save(byte_io, 'png') byte_io.seek(0) requests.post( url('/media/upload'), files={ 'files[]': ( '1.png', byte_io, 'multipart/form-data' ) }, ) print files gives me {'files[]': ('1.png', <_io.BytesIO object at 0x105b69290>, 'multipart/form-data')} and it does not error out. Continue reading...