file-upload.py

import requests
import pandas as pd
import os


# Config stuff
url="https://www.yourapp.com/add/new/file"
headers = {
    'User-Agent': 'Mozilla/5.0 (X11; Ubuntu; Linux x86_64; rv:47.0) Gecko/20100101 Firefox/47.0'
    # Add here more headers
}

# You may want to see the requests in some proxy (burp)
proxies = {
    'http': 'http://192.168.0.1:8080',
    'https': 'http://192.168.0.1:8081',
}


# For a given path, iterate through files and repeat the request
def do_fuzz(path):
    from glob import glob
    for f in glob(path):
        # Create attachment
        files = {
            'attachment': ("petter.jpg", open(f, 'rb'), 'image/jpeg'),
            'name': "image.jpg"
        }

        # Send attachment
        r = requests.post(
            url,
            headers=headers,
            proxies=proxies,
            verify=False,
            files=files
        )

        # Here do whatever with the response


# Do fuzzing
do_fuzz("/home/victor/fuzz/Pictures/*")