Installing Pip on Whonix Gateway

I understand this is a security risk but this is for testing reasons, not full blown production:

I want to run a Python Flask server on my Whonix Gateway to control Tor. The idea is to run a hidden service on the gateway and send commands to it over the Tor network. The problem is that pip will not update.

I ran the command: sudo apt-get install python-pip build-essential

After installing, I tried running “sudo pip install --upgrade pip” but was met with this error:
user@host:~$ pip install --upgrade pip Cannot fetch index base URL https://pypi.python.org/simple/ Could not find any downloads that satisfy the requirement pip in /usr/lib/python2.7/dist-packages Downloading/unpacking pip Cleaning up... No distributions at all found for pip in /usr/lib/python2.7/dist-packages Storing debug log for failure in /home/user/.pip/pip.log

So i checked the pip.log but got this: https://ghostbin.com/paste/7gun4

Any idea how to fix?

The Whonix way is to run the hidden service in the Whonix-Workstation. As per above link.

It’s also possible to reach Whonix-Gateway’s Tor ControlPort from Whonix-Workstation in a filtered, secure, configurable way using onionshare which is Whonix’s Tor control port filter. This may make more sense very most likely depending on your use case. More info:

onion-grater usage example:

If you’re adamant about doing it on the gateway, try.

sudo torsocks pip install --upgrade pip

Hey! Thank you so much! for now, im going to do it on gateway because I do not want to configure the two systems for an operation so small but I will look into this next time.

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