I'm trying to install the latest version of pip (currently 8.1.2) on the official ubuntu/trusty64 Vagrant box. The box comes with Python 2.7.6 and 3.4.3 pre-installed with apt-get. I read the pip More on stackoverflow.com

You'll need to include the complete error output from when you try to install something and it fails. More on reddit.com

In general, if a package is not available in the official repositories, you should not try to install it using pip as root. This can break things or in general cause a messy system that's difficult to debug when you have two versions of the same library installed. Instead, create a "virtual environment" (virtualenv) for your python project to work in. $ python3 -m virtualenv venv then, activate that virtual environment in the current terminal $ source venv/bin/activate Your terminal prompt will then change to show that you're in the virtual environment named "venv" (venv) $ after which, you can run any pip install commands as you please (venv) $ python3 -m pip install pyyaml Note that none of these commands should be run with sudo. In general, pip and other tools should not be run with sudo, as that will install libraries into unintended places and may cause issues. You should let your package manager (apt) handle system-wide libraries. If you're annoyed with having to enter the virtual environment every time you launch your script, add a "shebang" to the start of your script that points to your virtual environment's version of python. #!venv/bin/python3 then, make the script executable $ chmod +x scriptname.py this will allow you to run the script as simply $ ./scriptname.py even without being in the virtual environment. After you are done developing, you may want to make this portable. In which case, create a requirements.txt file by running the following command (venv) $ python3 -m pip freeze > requirements.txt this will create a requirements.txt file containing all the pip packages used in your project. To recreate the environment for use in another system, simply make the virtual environment in the other system and instruct pip to install the requirements. $ python3 -m virtualenv venv $ source venv/bin/activate (venv) $ python3 -m pip install -r requirements.txt the -r flag is important, as it indicates that you're giving it a requirements file. More on reddit.com

Python 2.7 is pretty old, I have transfered all my codes to Python 3, it has a higher performance, compatability etc. In your case, I would recommend to use conda (simply miniconda) and create a virtual environment with python=2.7, see conda instructions . I think it always good to isolate the environment from the global one from ubuntu, in order to not fuck up the latter More on reddit.com