Phase 5: Context Engineering · 20 min · Cursor · Claude Code · Lovable

Managing Context Across Sessions

New chat doesn't mean new project. Learn to hand off context so the AI picks up where you left off.

Hiring signal: What changes when you use this: you can maintain project continuity across sessions — which means you don't lose progress when you start a new chat.

What you will learn

Understand why new chats lose context and when that's good vs. bad
Write a handoff prompt that summarizes the current state for a new chat
Use context files for cross-session continuity
Know when to use the same chat vs. start a new one

Your Mission

Work on a project for 15-20 messages, write a handoff prompt, start a new chat, and evaluate continuity. Output: handoff_evaluation.md.

You need: Any AI coding tool with a project you can build.

Time: 30 minutes.

Step 1: Learn When to Start a New Chat (3 min)

New chat is GOOD when:

Chat is overloaded (60+ messages, AI forgetting things)
Starting a new, unrelated feature
Stuck in a correction loop (fresh context technique)
Chat has too many failed attempts

New chat is BAD when:

In the middle of a complex multi-step task
AI is actively making good progress
Haven't captured current state yet

The handoff prompt gives the new chat everything it needs:

"I'm continuing work on a project. Here's the current state: Project: [name + tech stack] What's done: [completed features] What I'm working on: [current task] Current issue: [specific problem + error] Conventions: [patterns to follow] Next step: [what to do now]"

The 30-message checkpoint
When your chat hits ~30 messages, pause and update your context file's "Current State" section. This is your checkpoint. If the chat continues smoothly, great. If the AI starts forgetting or you need to start fresh, your context file is ready. This habit takes 2 minutes and saves 20 minutes of re-explaining.

Unlock the full lesson

You've read the first 2 sections. The rest of this lesson covers Step 2: Start Building (10 min), Step 3: Write the Handoff Prompt (5 min), Handoff Prompt, Step 4: Start a New Chat (5 min), Step 5: Evaluate Continuity (5 min), Evaluation, Step 6: Update Context File (2 min), Context File Update, You're Done — plus a hands-on lab, quiz, and project artifact.

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