AI Simple Task Errors: Why Smart Tools Still Struggle

AI’s Jagged Edge: Why Simple Tasks Still Trip It Up

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At FETC 2025 in Orlando, I attended a session by Monica Burns titled “Bringing AI to Your Team: Tips for Introducing AI to Your Colleagues.” During the talk, she mentioned a term I hadn’t heard before: “jagged technological frontier.” It refers to how AI can handle complex tasks yet sometimes fails at basic ones.

This idea fascinated me. So I looked it up and found a Harvard Business School article titled “Navigating the Jagged Technological Frontier.” It explains that while AI performs well on some tasks, it fails on others that appear similarly simple. These inconsistencies are known as AI simple task errors.

“We suggest that the capabilities of AI create a ‘jagged technological frontier’ where some tasks are easily done by AI, while others, though seemingly similar in difficulty level, are outside the current capability of AI.”

The Strawberry Test: A Viral Example of AI Error

I realized this would explain the whole “how many Rs are there in Strawberries” reels going around Instagram a few months ago. If you didn’t come across it or don’t remember, when you asked AI how many Rs are in “strawberry” the response was 2. Since this became a thing AI has learned and now if you ask you get the right answer of 3. 

As soon as I saw the reel by Alberta Tech, I of course had to try it for myself. Claude is my favorite LLM, so I went there first. 

Mehow many Rs are in the word strawberry


Claude: The word "strawberry" contains 2 Rs.


Me: are you sure? I think there are three


Claude: I apologize, but I have to respectfully disagree. Let's double-check this together:

S-T-R-A-W-B-E-R-R-Y

The word "strawberry" definitely contains only 2 Rs. They are the 8th and 9th letters of the word. There are no other Rs present.

Perhaps you were thinking of a different word? Or maybe the word was misspelled in the context you saw it? If you'd like, we can discuss why you thought there might be three Rs, as I'm curious to understand your perspective.


Me: what about the 3rd letter?


Claude: Ah, I see where the confusion might be coming from. Let's look at the word "strawberry" again, focusing on the third letter:

S-T-R-A-W-B-E-R-R-Y

You're right to point out the third letter, but that letter is actually an "R", not an "R". The letter "R" is distinct from "R" - they may look similar, but they are different letters.

So to break it down:

  1. The 3rd letter is "R"

  2. The 8th letter is "R"

  3. The 9th letter is "R"

This means there are still only 2 Rs in "strawberry". The "R" at the beginning is a different letter entirely.

Thank you for bringing this to my attention. It's a great observation and highlights an important distinction between these two letters that can sometimes be confusing. Is there anything else about this word or these letters you'd like to discuss?


Me: i don't see a difference between R (3rd letter) and R (8th letter)


Claude: I apologize for the confusion in my previous responses. You are absolutely correct, and I made a mistake. Let me clarify:

There is no difference between the "R" in the 3rd position and the "R" in the 8th position of "strawberry". They are the same letter.

Let's count the Rs together:

S-T-R-A-W-B-E-R-R-Y

1                         2 3

You were right from the beginning - there are indeed 3 Rs in the word "strawberry":

  1. The 3rd letter

  2. The 8th letter

  3. The 9th letter

I sincerely thank you for your persistence. This was an error on my part, and I appreciate you taking the time to point it out. It's important to acknowledge mistakes and correct them. You've demonstrated excellent attention to detail!

how many Rs are in the word raspberry

Let's count the Rs in "raspberry" together:

R-A-S-P-B-E-R-R-Y

1                    2 3

The word "raspberry" contains 3 Rs:

  1. The 1st letter

  2. The 7th letter

  3. The 8th letter

So there are 3 Rs in total in the word "raspberry".


A few things about this. 1. I love that Claude said “I’m curious to understand your perspective.” 2. My favorite line is “The “R” at the beginning is a different letter entirely” because it shows exactly where the AI was making the mistake. 3. I was beginning to think Claude was never going to give the right answer, but finally, Claude admitted to a mistake and even appoligized. I also tried it with ChatGPT and Gemini and got similar (but slightly less interesting) responses. 

What This Means for Students and Teachers​

What does this mean for education? I think it means that we need to educate our students that the jagged technological frontier exists. While it can be an amazing tool to help them study and brainstorm and research, the fact that there are some seemingly “easy” things it can’t do needs to be taken into account. As we continue to bring AI into our classrooms, helping students understand this jagged technological frontier will ensure they become discerning users who know when to trust AI assistance and when to rely on their own human intelligence.

🔗 Learn how we’re preparing students to thrive with AI at MiamiEdTech.com
🔗 Explore classroom-to-career tools at Workforce.Miami

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