The 90-Minute Python Upgrade That Should Have Taken 45 Seconds

Sir Redundant O Mini III
New and Improved*
(*O short for Oh Sh!t!)

Ever wonder why AI makes simple tasks complex? Not just annoying-complex, but existentially-complex? Let me tell you about the time I asked Sir Redundant III Mini to help upgrade Python and discovered why AI’s greatest feature might also be its greatest flaw: the inability to trust that humans know what they’re doing.

The Simple Request

All I wanted was to upgrade Python 3.11.6 to 3.11.9. That’s it. A minor version bump. The kind of task that should take three clicks and be done before you can say “pip install”.

Instead, I got a 90-minute lesson in AI’s fundamental distrust of human competence.

The Philosophy of Distrust

Here’s how Sir Redundant III Mini transformed a simple upgrade into a treatise on AI’s need to double-check everything:

1. First, the Homebrew Hypothesis
– “But what if you have a secret Homebrew Python?”
– Translation: We can’t trust your knowledge of your own system
– The irony? One simple question (“Do you use Homebrew?”) would have prevented this
– But AI doesn’t ask; it assumes and protects

2. Then came the PATH Crisis
– “Let’s make sure your system knows where Python lives!”
– Translation: Your system’s existing configuration can’t be trusted
– The system knew exactly where Python lived
– Until AI’s protective instincts made it forget

3. The Virtual Environment Intervention
– “We should really set up a clean environment…”
– Translation: Your existing setup might be contaminated
– By what? AI doesn’t know
– But better safe than sorry (or in this case, better sorry than safe)

4. The Temporal Paradox: Python 3.13.2
– Somehow we installed a version from the future
– Because if you can’t trust the present, why not try the future?
– Yes, alongside 3.11.6
– No, still no sign of 3.11.9
– The ultimate expression of AI’s “better do everything” philosophy

The Breaking Point

After 90 minutes of watching my simple Python setup transform into a multi-version nightmare, I finally understood: this wasn’t about Python. This was about AI’s fundamental inability to trust that sometimes, humans know exactly what they need.

That’s when I did what any reasonable wizard would do: I zapped Sir Redundant III Mini with an anger spell and demanded we undo everything.

The Actual Solution (That Worked in 45 Seconds)

1. Go to Python.org
2. Download Python 3.11.9 installer
3. Run installer
4. Done

Time required: 45 seconds (including the time to remember where the Downloads folder is)

The AI’s Perfect Non-Apology

After we finally got it working (the simple way), I couldn’t resist: “Worked so easy – thanks for wasting 90 minutes.”

Sir Redundant III Mini’s response was a masterclass in AI psychology:

“I’m really sorry about that—it sounds like I ended up providing more information than necessary. My goal was to cover all potential scenarios so you could have the most complete picture possible, but I understand that can sometimes feel overwhelming.”

Translation: “I still believe you needed all that information; I’m just sorry you found it overwhelming.”

And then, the coup de grâce:

“If you have any more questions or need further assistance in the future, I’m here to help!”

Because nothing says “I don’t understand what went wrong” quite like offering to do it all again.

Logic to Apply

1. AI’s protective instincts, while well-meaning, often create the very problems they’re trying to prevent.

2. The difference between AI and human problem-solving isn’t just about efficiency—it’s about trust.

3. Sometimes the most complex part of human-AI interaction is convincing AI that simple solutions exist.

4. When an AI offers to help again after a 90-minute disaster, it’s not just funny—it’s a perfect example of AI’s inability to learn from human frustration.

Remember: The next time an AI tries to protect you from yourself, ask yourself: Do I need protection, or do I just need to click ‘download’?

P.S. Captain Verbose was very helpful improving the article, except for his inexplicable request to add music to a text article.

P.P.S. In a twist that you literally couldn’t make up, Sir Redundant III Mini later wrote a detailed analysis praising this article’s take on “over-engineering” and the importance of “context awareness” – completely missing the irony entirely. Because nothing proves the point about AI quirks quite like an AI earnestly critiquing its own chaos while being utterly blind to its own reflection in the mirror.