"OverflowError: string longer than 2147483647 bytes" when trying requests.put

I’m having the same basic issue as @gjedeer and see the same behavior as @cmbasnett (that wrapping in BytesIO is not a solution). I’m trying to use a file object to upload something larger than 2GB using a TLS encrypted post. Specifically I’m trying to use a presigned url to upload a file to S3. It appears that the underlying ssl library in python doesn’t like files over 2GB. Is there an accepted workaround to this? Stack trace:

Basic code:

 with open(self.path_to_data, 'rb') as f:
    fields = 'defined elsewhere...'
    files = {'file': f}
    request('post', url, data=fields, files=files)

Traceback (most recent call last):
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/bin/mds", line 11, in <module>
    load_entry_point('mdscli', 'console_scripts', 'mds')()
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/click/core.py", line 764, in __call__
    return self.main(*args, **kwargs)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/click/core.py", line 717, in main
    rv = self.invoke(ctx)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/click/core.py", line 1137, in invoke
    return _process_result(sub_ctx.command.invoke(sub_ctx))
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/click/core.py", line 956, in invoke
    return ctx.invoke(self.callback, **ctx.params)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/click/core.py", line 555, in invoke
    return callback(*args, **kwargs)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/click/decorators.py", line 64, in new_func
    return ctx.invoke(f, obj, *args, **kwargs)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/click/core.py", line 555, in invoke
    return callback(*args, **kwargs)
  File "/Users/coltonhicks/dev/mds_cli/mdscli/cli.py", line 133, in upload_member_data
    uploader.main()
  File "/Users/coltonhicks/dev/mds_cli/mdscli/upload_member_data.py", line 30, in main
    self.client.upload_member_data(self.mida, self.data_type, f)
  File "/Users/coltonhicks/dev/mds_cli/mdscli/requests_client.py", line 300, in upload_member_data
    logger.info(
  File "/Users/coltonhicks/dev/mds_cli/mdscli/requests_client.py", line 186, in _request
    res = requests.request(method, url, data=data, files=files)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/requests/api.py", line 60, in request
    return session.request(method=method, url=url, **kwargs)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/requests/sessions.py", line 533, in request
    resp = self.send(prep, **send_kwargs)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/requests/sessions.py", line 646, in send
    r = adapter.send(request, **kwargs)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/requests/adapters.py", line 449, in send
    timeout=timeout
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/urllib3/connectionpool.py", line 603, in urlopen
    chunked=chunked)
  File "/Users/coltonhicks/.virtualenvs/mds_cli-AtYG3_5U/lib/python3.7/site-packages/urllib3/connectionpool.py", line 355, in _make_request
    conn.request(method, url, **httplib_request_kw)
  File "/usr/local/Cellar/python/3.7.3/Frameworks/Python.framework/Versions/3.7/lib/python3.7/http/client.py", line 1229, in request
    self._send_request(method, url, body, headers, encode_chunked)
  File "/usr/local/Cellar/python/3.7.3/Frameworks/Python.framework/Versions/3.7/lib/python3.7/http/client.py", line 1275, in _send_request
    self.endheaders(body, encode_chunked=encode_chunked)
  File "/usr/local/Cellar/python/3.7.3/Frameworks/Python.framework/Versions/3.7/lib/python3.7/http/client.py", line 1224, in endheaders
    self._send_output(message_body, encode_chunked=encode_chunked)
  File "/usr/local/Cellar/python/3.7.3/Frameworks/Python.framework/Versions/3.7/lib/python3.7/http/client.py", line 1055, in _send_output
    self.send(chunk)
  File "/usr/local/Cellar/python/3.7.3/Frameworks/Python.framework/Versions/3.7/lib/python3.7/http/client.py", line 977, in send
    self.sock.sendall(data)
  File "/usr/local/Cellar/python/3.7.3/Frameworks/Python.framework/Versions/3.7/lib/python3.7/ssl.py", line 1015, in sendall
    v = self.send(byte_view[count:])
  File "/usr/local/Cellar/python/3.7.3/Frameworks/Python.framework/Versions/3.7/lib/python3.7/ssl.py", line 984, in send
    return self._sslobj.write(data)
OverflowError: string longer than 2147483647 bytes

@SpoonMeiser Wrapping the file contents in a BytesIO does not fix the problem on Python 3.6, still raises the exact same error.