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Context Window : The real limit most developers miss

Developers argue a lot about AI coding tools. Some say they’re bad. Others say it’s a skills problem. A common real gap is understanding the context window. This is the main limit for most AI coding agents today.

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What the context window is

The context window is the model’s short-term memory.
It’s the text the model can see at once. That includes what you send in and what the model sends back.

Models don’t remember between calls. The chat app stores the history and resends it each time. That history fills the context window.

What goes into the window:

  • Input tokens: Your messages, system prompts, files, or retrieved data.

  • Output tokens: The model’s responses.

As you keep chatting, the window fills and token use rises.

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Tokens — the model’s building blocks

Models work with tokens, not characters. A token can be a character, part of a word, a whole word, or a short phrase.
Rough rule: one English word ≈ 1.5 tokens. So 100 words ≈ 150 tokens. Different tokenizers vary.

Hard limits and what happens when you hit them

Each model has a max token limit set by the provider. If you go over it, the model can stop or throw an error.
Limits vary a lot. Some older models had 4,000 tokens. Newer ones can handle hundreds of thousands — even millions in some cases.

Why limits exist:

  • Cost: More tokens need more compute. Doubling tokens can raise compute costs a lot.

  • Memory: Long contexts need more VRAM and RAM.

  • Performance: More context doesn’t always help. Sometimes it makes results worse.

The “lost in the middle” problem

Bigger context windows don’t fix everything. Models struggle to pick a small detail from a huge block of text. They focus more on the start and the end of the input. That’s like primacy and recency bias in humans.

When the model misses context, it guesses. That can produce serious hallucinations.

How to manage context for better results

Keep the context lean and focused. Small context windows work better for coding agents.

Practical steps:

  • Watch token use. Know how many tokens you’ve used and the limit.

  • Clear history regularly. Resetting the chat gives the model a clean slate.

  • Compact conversations. Some tools can summarize and replace long history with a short summary. That keeps intent without the full text.

  • Start new chats for new topics. If you switch ideas, start fresh.

  • Avoid bloating system prompts and tool configs. Large rules files or tool prompts can eat tokens fast.

  • Chunk large texts. Break big documents into parts, summarize each, then summarize the summaries.

Technical and safety notes

The model uses self-attention to score relevance across tokens. For long chats, developers use optimizations like:

  • Flash Attention: Processes tokens in efficient chunks to save memory.

  • K/V cache tricks: Compresses context data to reduce VRAM use.

Long contexts also raise safety risks. More text means more places for hidden or malicious prompts. That can make jailbreaking easier.

Bottom line

Think of the context window like a whiteboard. It holds what the model is working on right now. It has a fixed size. Once it’s full, the model struggles to find details buried in the middle.

If you want steady results, keep the board clean. Clear old stuff. Summarize where useful. Start new chats when you change topics. A focused context helps the model help you.