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World desk2 min

AI Tokens: Why “Strawberry” Can Fool a Language Model

Tokens encode text for language models, but they are not individual characters. Here’s what that means—and how to verify an exact letter count.
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A token is a unit a language model uses to encode text; it can be a whole word or a piece of one, not necessarily a single character. “Strawberry” contains three r’s: s-t-r-a-w-b-e-r-r-y. A 2024 OpenAI Developer Community thread records users getting an answer of two, but it does not establish why that happened or how often models make this mistake.

What a token is

Before a language model processes text, a tokenizer converts it into numerical units called tokens. A token may correspond to a whole word or a sub-word piece. The units depend on the tokenizer, so there is no universal rule that one word, one letter, or a fixed fraction of a word equals one token. OpenAI’s tokenizer lets you inspect how text is divided for a particular model.

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Why “strawberry” can trip up an AI

The word has three r characters: one in “str” and two together near the end. The 2024 OpenAI Developer Community discussion documents users asking how many r’s are in “strawberry” and receiving the answer “two.” It is an example of an incorrect response, not a controlled test or a measure of how often the error occurs.

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Tokenization helps explain why a model’s text units are not the same thing as letters, but it does not prove why that particular answer was wrong. The available account does not show how the reported model split “strawberry.” OpenAI’s gpt-oss model card describes o200k_harmony as a Byte Pair Encoding tokenizer extending o200k; that is an example of a model-specific encoding, not evidence of the split used in the community report. More broadly, a model can generate a plausible-sounding answer and still fail at an exact character-count task.

When token counts matter

Tokens are operational units, not just a technical curiosity: the OpenAI API reference reports input and output token usage. Because tokenization varies by model, a token count is not interchangeable with a count of characters or words.

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How to count letters reliably

If the question is how many times a particular letter appears, count the literal characters rather than inferring the answer from a model’s text units. For “strawberry,” spelling the word out makes the count clear: s-t-r-a-w-b-e-r-r-y has three r’s. For longer text, use a deterministic string-counting method and check that it is counting the exact character you intend.

A tokenizer and a string counter answer different questions. A tokenizer shows how a model encodes text; a string counter counts literal characters. Inspecting tokens can help understand model input, but it does not verify a character count.

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