Insecureplatformwarning: A true SSLContext object is not available. This prevents urllib3 from configuring SSL appropriately

The steps to victory

Before you hit the command line, let's demystify the InsecurePlatformWarning and chalk out our strategy to defeat it:

Confirming Python's age

An older Python could be allowing the SSL monster to rear its head. Upgrade to Python 2.7.9+ or a Python 3 mentor to enable native SSL support:

python --version #I see dead versions! 👀💀

Perform a resurrection if required:

# Linux/macOS
sudo apt-get install python3

# Windows
# Time travel at: https://www.python.org/downloads/windows/

Refresh 'requests' and its squadron

Occasionally, promoting requests and its team to the next rank solves the problem:

pip install --upgrade requests
pip install 'requests[security]' # Unlocks secret weapons! 🔓🦸‍♂️

Enhance Your Arsenal on Ubuntu

For Ubuntu soldiers, you might need libffi-dev and libssl-dev to make pyOpenSSL bulletproof:

sudo apt-get install libffi-dev libssl-dev

Check 'requests' service record

Referring to setup.py from the requests platoon or its bugfix medal citations can shed light on version-specific battles. Thus, relegating requests to Version 2.5.3 might help you go undercover momentarily:

pip install requests==2.5.3 # Nostalgic uniforms sometimes work! 🕰️👮

Vet OpenSSL’s credentials

pyOpenSSL requires a compatible OpenSSL warrior. Check its rank using:

openssl version # Friendly or foe? 🤔

Call for reinforcements if required:

sudo apt-get install openssl

Path for the undefeated: persistent SSL issues

Even the best can fall. If you're cornered by SSL issues despite the major steps, here's your escape plan:

Detailed check of your gear

Make sure all your packages are battle-ready and there's no infighting. Conduct a roll call with pip list to see installed versions of pyOpenSSL, ndg-httpsclient, and pyasn1, and verify their minimum required ranks.

Evaluate field strategies

System-wide recon or changes in your OpenSSL configurations could tip Python's balance in establishing secure connections. Consult your battle manual (OS documentation) for SSL configuration tactics.

Plan Python 3 migration

Stuck in the Python 2.x trenches? Time to upgrade! Python 3.x has a fortified SSL module and receives active strategy updates for better security and compatibility.

Refer to the command center

Don't forget the wealth of intel available in Stack Overflow answers, bug reports, or Python's extensive documentation—the references below can be your secret map to victory.