Why My Cursor AI Kept Forgetting Files and How I Fixed the Context Chaos

I was deep into a complex coding project using Cursor, the AI-powered IDE, when everything suddenly stalled. Every chat with the AI became a gamble—sometimes it remembered my files, other times it acted like we’d never met. That unpredictability cost me hours. So I rolled up my sleeves to solve this for good.

The Core Problem: Inconsistent Context Handling

Here’s what kept tripping me up: I’d attach a file to a chat, only to have the AI blank on it moments later. Picture this—I’d manually edit my code, reattach the file, and get suggestions based on the old version. My updates? Totally ignored.

I even stopped using handy features like codebase search (Ctrl+Enter) because I worried it would crowd out previous messages. The uncertainty made me second-guess every interaction.

My Step-by-Step Journey to Clarity

I tested every scenario I could imagine and dug through documentation. Turns out, Cursor doesn’t automatically hold onto file context between messages. You’ve got to deliberately include files each time to show the AI your latest work. Here’s how I cracked it:

• Reattach Every Time: Started including files in every single message—even if we’d just discussed them. Suddenly, the AI consistently referenced my current code.
• Respect the Limits: Learned that attaching massive files can overload the AI’s memory. Now I use the @ symbol to highlight specific functions or classes, keeping things focused.
• Smarter Searches: Only run codebase searches when absolutely necessary. When results get messy, I manually attach just the files I need.

These simple changes transformed my workflow from frustrating to functional.

Key Insights for Reliable AI Workflows

After all that testing, three rules became my north star:

• Treat files like perishable goods—reattach them after every edit to keep things fresh
• Use @filename like a laser pointer to guide the AI exactly where to look
• Assume nothing’s private—avoid attaching sensitive files until security improves

While testing, I noticed some documentation gaps too—like clearer examples for .mdc files and installation guides. Really hope those get attention soon.

Now my Cursor workflow actually works. The AI stays on track, and I get more coding done. If you’re wrestling with similar context glitches, try these steps—they saved my sanity. Watch for updates as the docs improve!