You are using pip3 to install flask-script which is associated with python 3.5. However, you are trying to upgrade pip associated with the python 2.7, try running pip3 install --upgrade pip.

It might be a good idea to take some time and read about virtual environments in Python. It isn't a best practice to install all of your packages to the base python installation. This would be a good start: http://docs.python-guide.org/en/latest/dev/virtualenvs/

Answer from JanHak on Stack Overflow
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River
river.me › blog › change-pip-version
Update pip/pip3 to Python 3.8 in Ubuntu – River Writes - A MediaWiki Blog
April 11, 2021 - python3 -m pip install --upgrade --force-reinstall pip · What a helpful warning! So I added /home/river/.local/bin/ to my $PATH (before doing this, I echo $PATH’d just in case I messed up): ... And I also put it into ~/.profile and ~/.config/fish/config.fish per this Ask Ubuntu post.
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Readthedocs
neoctobers.readthedocs.io › en › latest › python › update_to_pip3_on_ubuntu.html
Update pip3 to 18.x on Ubuntu 18.04 LTS — neoctobers latest documentation
Update pip3 to 18.x on Ubuntu 18.04 LTS · Edit on GitHub · Check for python3 version: # python3 Python 3.6.7 (default, Oct 22 2018, 11:32:17) [GCC 8.2.0] on linux Type "help", "copyright", "credits" or "license" for more information. >>> Install pip3: # wget https://bootstrap.pypa.io/get-pip.py # python3 get-pip.py ·
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Python⇒Speed
pythonspeed.com › articles › upgrade-pip
Why you should upgrade pip, and how to do it
March 21, 2023 - In general, you can do pip install --upgrade pip and call it a day. However, in some environments that can have issues. For example, if you look above at how we setup Python in Ubuntu 18.04, we installed pip from a system package.
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Namehero
namehero.com › blog › install-pip3-on-ubuntu-the-ultimate-guide
Install Pip3 On Ubuntu: The Ultimate Guide
December 9, 2024 - The entire process begins with ... to Ubuntu and then install pip3. Terminal can be opened by either going to the Application Launcher through the desktop interface and selecting “Terminal” or you can press and hold Ctrl + Alt + T as a shortcut ...
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Squash
squash.io › how-to-upgrade-pip3-in-python
How to Upgrade Pip3 in Python - Squash Labs
November 2, 2023 - A guide on upgrading Pip3, the Python package installer.
Find elsewhere
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Webhi
webhi.com › home › how to install pip3 in ubuntu
How to install Pip3 in Ubuntu - Tutorial & Documentation
April 5, 2023 - $ sudo pip3 install --upgrade pip · With pip installed on your Ubuntu machine, you can begin installing Python packages available in the Python Package Index (PyPI). You can then use a variety of commands to manage these packages with pip.
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PhoenixNAP
phoenixnap.com › home › kb › sysadmin › how to install pip on ubuntu
How to Install Pip on Ubuntu
December 11, 2025 - To install Pip for Python 3 on ... by running the following command: ... 4. To upgrade pip3 to the latest version, add --upgrade to the command just like for any other PyPI package:...
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Cherry Servers
cherryservers.com › home › blog › cloud computing › how to install pip on ubuntu 22.04 | step-by-step
How to Install PIP on Ubuntu 22.04 | Step-by-Step | Cherry Servers
February 20, 2026 - pip3 install --upgrade package-name pip3 install -U package-name · For example, to update the matplotlib package, run the command: ... If the package is already in its latest version, no change will be affected.
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Codedamn
codedamn.com › news › python
How to Update Pip and Python On Your System With Pip Upgrade
June 22, 2023 - For Debian-based systems (e.g., Ubuntu), run the following commands: ... After updating, verify the updated version by running python --version or python3 --version, depending on the version you installed.
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GitHub
github.com › pypa › pip › issues › 6444
pip3 upgrade should not update pip binary · Issue #6444 · pypa/pip
April 25, 2019 - sudo apt-get install pip) you get pip3 for Python 3.x. If you run sudo pip3 install pip ---update it will update pip3, but it will also update the pip binary and now running pip to install a package will install the package for Python 3.x, not 2.x
Author   pypa
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Anglehit
anglehit.com › how-should-i-upgrade-pip-on-ubuntu
How should I upgrade pip on Ubuntu? – Anglehit
January 29, 2020 - Let’s say you’ve copied a giant chunk of data from a source to destination something like this: Now you wish to undo this command. Phew!!! Solution: This can be achieved using a python · This post is relative to all the novice as well as seasoned users on laptop specially — considering ...
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BitLaunch
bitlaunch.io › blog › how-to-upgrade-pip
How to upgrade your pip package to the latest version
December 20, 2025 - Upgrading pip is again very easy process. Just run the following: ... Bear in mind that this command will try to uninstall the current version and replace it with the new one. If you see the message Not uninstalling pip at /usr/lib/python3/dist-packages, outside environment /usr, it’s because you’re using Ubuntu.
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Ask Ubuntu
askubuntu.com › questions › 919134 › how-to-update-pip3-sub-version
python - How to update pip3 sub-version? - Ask Ubuntu
May 26, 2017 - I upgraded my Ubuntu server from 15.04 to 16.04 LTS recently. In the process, Python 3.5 was installed. However, the version of pip3 that comes with it apparently wants to use python 3.4 for some r...
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NBShare
nbshare.io › notebook › 228803083 › How-to-Upgrade-Python-PIP
How to Upgrade Python PIP - Nbshare Notebooks
pip (19.3.1) - The PyPA recommended tool for installing Python packages. You are using pip version 9.0.1, however version 19.3.1 is available. You should consider upgrading via the 'pip install --upgrade pip' command.
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LinuxVox
linuxvox.com › blog › ubuntu-install-pip3
Installing `pip3` on Ubuntu: A Comprehensive Guide — linuxvox.com
Regularly update pip3 itself to ensure you have the latest features and security patches. ... Also, periodically upgrade all your installed packages to their latest versions.
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Educative
educative.io › answers › installing-pip3-in-ubuntu
Installing pip3 in Ubuntu
Use the apt-get -y install python3-pip command to install pip3, if Python 3 is already installed on your Ubuntu system.