Multi-Day Sessions: Maintaining Context Across Days

intermediate 12 min 📋 Copy-paste ready

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sessionscontinuityslash-commandsworkflowclaude-code

Scenario

Context: You're working on a feature that spans multiple days and need to maintain context between sessions

Goal: Learn techniques and commands for maintaining continuity across multi-day AI-assisted development

Anti-pattern: Starting each session from scratch with no context, repeating explanations

Tools: Claude CodeGitHub Copilot

Conversation

The Multi-Day Session Problem

AI assistants don't remember previous sessions by default. Each conversation starts fresh. This creates friction when working on features that span days or weeks.

Solutions:

1. CLAUDE.md files - Persistent context loaded automatically
2. Session tracking commands - Document progress in-conversation
3. Resume flags - Continue previous conversations
4. Scratchpad files - Track state in version control

Day 1: Starting a Feature with Session Tracking

Using the claude-sessions extension or similar custom commands:

👤 You

/project:session-start auth-system-refactor

Starting a named session creates a tracking file and timestamps your work.

🤖 AI

Session started: auth-system-refactor
Timestamp: 2024-01-15 09:00:00
Tracking file: .claude/sessions/auth-system-refactor.md

I'm ready to help with the auth system refactor. What's the current state and goal?

The session is now being tracked. Progress will be logged to a file you can reference later.

👤 You

We need to migrate from session-based auth to JWT. Current codebase uses express-session with Redis. Goals:

1. Replace session middleware with JWT verification
2. Add refresh token rotation
3. Keep backward compatibility during migration

Provide comprehensive context at session start - this will be captured for future reference.

🤖 AI

Understood. Let me outline the migration plan:

JWT Migration Plan

Phase 1: Add JWT Infrastructure (today)

• Create JWT service (sign, verify, refresh)
• Add new auth middleware that accepts both session AND JWT
• Database: Add refresh_tokens table

Phase 2: Dual-Mode Operation (this week)

• Update login endpoint to issue JWTs alongside session
• Clients can opt-in to JWT mode
• Monitor adoption metrics

Phase 3: Deprecation (next week)

• Log warnings for session-only requests
• Set sunset date for session auth

Phase 4: Removal

• Remove express-session middleware
• Clean up Redis session store

Shall I start with the JWT service?

The AI establishes a clear multi-phase plan that naturally spans multiple days.

👤 You

Yes, start with the JWT service. I'll need to stop for the day after this component.

Signaling session end helps the AI provide a good stopping point with context capture.

🤖 AI

[Implements JWT service with sign, verify, refresh methods...]

// src/services/jwt.service.ts
export class JWTService {
  async signAccessToken(userId: string): Promise<string> { ... }
  async signRefreshToken(userId: string): Promise<string> { ... }
  async verifyAccessToken(token: string): Promise<TokenPayload> { ... }
  async rotateRefreshToken(oldToken: string): Promise<TokenPair> { ... }
}

Created:

• src/services/jwt.service.ts - Core JWT logic
• src/types/auth.ts - Token type definitions
• migrations/20240115_refresh_tokens.sql - Database schema

Ready for day-end wrap-up when you are.

The AI provides a clear summary of what was created, making resumption easier.

👤 You

/project:session-end

Ending the session triggers an automatic summary that captures state for resumption.

🤖 AI

Session Summary: auth-system-refactor

Duration: 2 hours 15 minutes
Date: 2024-01-15

Completed

• JWT service implementation
• Refresh token rotation logic
• Database migration for refresh_tokens
• Type definitions for tokens

In Progress

• Dual-mode auth middleware
• Login endpoint JWT issuance

Next Steps

1. Create hybrid auth middleware (accepts session OR JWT)
2. Update /auth/login to return tokens
3. Add /auth/refresh endpoint

Key Decisions Made

• Access token expiry: 15 minutes
• Refresh token expiry: 7 days
• Refresh token rotation: Single-use (invalidate on use)

Files Modified

src/services/jwt.service.ts (new)
src/types/auth.ts (new)
migrations/20240115_refresh_tokens.sql (new)

---

Session saved to .claude/sessions/auth-system-refactor.md
Resume tomorrow with /project:session-start auth-system-refactor

The session summary captures everything needed to resume: completed work, next steps, and key decisions.

---

Day 2: Resuming with Full Context

The next morning, you can resume with full context preserved:

👤 You

claude --continue

The `--continue` flag resumes your most recent conversation with full context.

🤖 AI

Welcome back! Resuming session: auth-system-refactor

Yesterday we completed the JWT service. Today's focus:

1. Create hybrid auth middleware
2. Update login endpoint
3. Add refresh endpoint

Shall I start with the hybrid middleware?

With session files or --continue, the AI remembers exactly where you left off.

---

Alternative: Using CLAUDE.md for Persistent Context

If you prefer not to use session commands, maintain a CLAUDE.md file that Claude loads automatically:

# Auth System Refactor

## Current Status
Phase 1 complete (JWT service). Working on Phase 2 (dual-mode).

## Key Files
- src/services/jwt.service.ts - JWT sign/verify/refresh
- src/middleware/auth.ts - TODO: Add JWT support

## Decisions
- Access token: 15min, Refresh token: 7 days
- Refresh rotation: Single-use

## Next Actions
1. Hybrid auth middleware
2. Login endpoint JWT issuance

Update this file at the end of each session. Claude reads it automatically on startup.

---

Programmatic Session Resumption

For automated workflows, capture and resume sessions by ID:

# Capture session ID from first interaction
session_id=$(claude -p "Start auth refactor" --output-format json | jq -r '.session_id')

# Later, resume with that session
claude --resume "$session_id" -p "Continue with the middleware"

This is useful for CI/CD pipelines or scripts that need multi-step AI assistance.

👤 You

/project:session-update Added hybrid middleware, tests passing

Mid-session updates capture progress without ending the session.

🤖 AI

Progress logged:

[2024-01-16 14:30] Added hybrid middleware, tests passing

Git status:
- Modified: src/middleware/auth.ts
- Added: tests/middleware/auth.test.ts
- 4 files changed, 127 insertions

Notes appended to .claude/sessions/auth-system-refactor.md

Remaining for today:

• Login endpoint JWT issuance
• Refresh endpoint

Session updates capture git state automatically, creating an audit trail of your work.

Key Takeaways

• Use `/project:session-start [name]` to begin tracked multi-day work
• Use `/project:session-end` to generate summaries with next steps
• Use `claude --continue` to resume your most recent conversation
• Maintain `CLAUDE.md` as persistent context that loads automatically
• Update session files at natural stopping points to capture decisions

Try It Yourself

Prompt Template

/project:session-start [feature-name]

I'm working on [describe feature]. Current state: [what exists]. Goal: [what we're building].

Let's start with [first component].

Copy template

Variations to Try

• End of day: `/project:session-end`
• Next day: `claude --continue` or re-explain context
• Progress update: `/project:session-update [what you accomplished]`
• Custom: Add session commands to `.claude/commands/session-start.md`

Related Content

📖 Context Windows 📖 Tokens & Tokenization 📖 Structured Outputs & JSON Schema 🏋️ context management

Sources

✓ Anthropic: Session Management ⓘ

×

Claude Code: Best practices for agentic coding

Anthropic

Official best practices for Claude Code agentic development. Key for agentic_supervision dimension - demonstrates multi-file autonomous editing capabilities and supervision approaches.

Key Findings:

• Claude Code is a command line tool for agentic coding
• CLAUDE.md provides project-specific context and instructions
• Plan mode shows intentions before making changes

Credibility: high

View Source ↗

✓ Ian Nuttall: Commands ⓘ

×

Claude Sessions: Development Session Tracking for Claude Code

Provides a practical implementation of session tracking for Claude Code. The workflow pattern (/project:session-start -> /project:session-update -> /project:session-end) creates documentation that enables continuity across multi-day work sessions. Key for agentic_supervision dimension - demonstrates how to maintain oversight and context in long-running projects.

Key Findings:

• Custom slash commands for session tracking across multi-day work
• Commands: /project:session-start, /project:session-update, /project:session-end
• Automatic git status capture at session boundaries

Credibility: medium

View Source ↗