When Does Context Break?

Relax. We're not going to explain this chapter like a textbook — just like a friend talking you through it, in plain, easy-to-follow terms.

Let's think about it this way for a second

Remember three failure patterns. 1) Wrong text — an unrelated passage, someone else's notes. 2) Stale text — last year's syllabus, an old rule that's already been updated. 3) Too much text — 200 chat messages, 5 PDFs, a long tool log. The model can be confidently wrong. Drop a rotten fish into the soup and the whole pot smells like it. Polishing the prompt won't get rid of that smell.

Let's connect it to everyday life

A good turn — question + a short handbook excerpt + "say so if you can't find it." A broken turn — question + the entire past chat + a random wiki page + yesterday's wrong answer. In week one, don't let your context run past half a page. If you need more, search with RAG first, then add in a short excerpt. Don't dump a whole bag of salt into the soup.

Catch all three: wrong, stale, and too much
Start with half a page
When it breaks, look at the table, not the prompt

Let's try it out together

text

Breaks when you pack:
- the wrong paragraph
- last year's rule
- the whole week of chat

Fix: keep 1–2 fresh, relevant notes

You should see

Tell apart the three ways context breaks down.

5-Minute Try

Think of 4 wrong outputs. For each one, note whether it was wrong text, stale text, too much text, or a fuzzy prompt.

One Quick Heads-Up

A nice-sounding answer doesn't mean the context was right. Go back and re-read what was actually on the table before you trust it.