Multi-session workflows

Most real work takes more than one session. Reports span days. Audits stretch across a week. Client setups spread across multiple logins. Multi-session workflow is the pattern that makes this work without losing context.

The pattern

1. Session 1: start the work, get it partway done, /wrapup with clear pending items
2. Session 2: /startup loads where you left off, continue, /wrapup
3. Session N: repeat until done

Each session builds on the last. Memory carries forward. You never start from zero after session 1.

What makes it work

Clear pending items at each /wrapup

The pending items from session N become the to-do list for session N+1. Make them specific and actionable, not vague:

Vague: "Continue the report"

Specific: "Finish the Meta section (sections 1-2 done). Add the creative breakdown chart. Request client sign-off before publishing."

Specific pending items = session N+1 starts fast.

Check in at /startup

When you /startup, Claude recaps. Before you start working, tell Claude:

Read the last 3 session summaries for this project. What's the full arc? What's still outstanding?

Forces Claude (and you) to see the project as a whole, not just the last session. Catches drift.

Update project context as you learn

Over multiple sessions you learn more about the project - client preferences, data quirks, campaign history. Save those to the project record:

Add to the project record for [key]: client prefers ROAS over CPA, all reports exclude mobile ad spend, deadline is always Friday EOD AEST.

Every future /startup loads these. You stop re-learning the same things.

Resuming a lost or interrupted session

Sometimes a session ends before you hit /wrapup. Your laptop runs out of battery. You close the terminal by accident. A deploy reboots the machine. The session isn't saved to memory yet - but Claude Code keeps the raw session history locally on your machine.

Two commands get it back.

Resume the most recent session

terminal
claude --continue

Starts Claude Code and loads the last session you had in this folder - every message, every tool call, every approval - exactly where you left off. Use this when you just want to pick up from where you were 5 minutes ago.

Shortcut: claude -c

Pick from a list of past sessions

terminal
claude --resume

Shows a picker of your recent sessions in this folder. Arrow keys to highlight one, Enter to load. Use this when you want to pull up a session from earlier today or yesterday - not just the most recent.

When to resume vs start fresh

Resume when

• Session crashed before you could /wrapup
• You closed the terminal by accident
• You're mid-task and want the full conversation context back

Start fresh instead when

• Session ended cleanly with /wrapup - memory has the summary, fresh session is lighter + sharper
• Context was already over 50% - resuming reloads the same bloat, degraded quality comes back with it
• You're switching to different work - resume a session that was about something else and Claude gets confused

Rule of thumb: if /wrapup ran, start fresh. If /wrapup didn't run, resume and then /wrapup properly.

After a resumed crash

First thing: run /wrapup to save what was in that session to memory. Don't work inside the resumed session for long without wrapping - if it crashes again, you lose it again.

Cross-session search

When you need to remember something from way back

Search my session_memories for any session where we worked on [topic]. Show me the summaries.

Or for a decision

When did we decide to exclude branded search conversions from the weekly report? Find that session and summarise the reasoning.

Claude does a full-text search across every session you've ever /wrapped. Your memory layer turns into a searchable journal.

Long-running projects

For projects that span months

• Weekly audit of pending items - some will be stale, cross them off; some need to be re-prioritised
• Monthly memory review - Module 04 audit process applied to this specific project
• Milestone /wrapups - when you hit a milestone (phase complete, deliverable shipped), do a longer /wrapup that captures the full arc of that phase

When to start a fresh project record vs continue

Sometimes you're not sure if new work is part of an existing project or a new one.

Same project if

• Same client, same business unit
• Continuation of an ongoing initiative
• Builds on past decisions + context

New project if

• Different client
• Same client but totally different work type (e.g. SEO audit vs paid media)
• Time-boxed campaign or launch that will end

When in doubt, ask Claude

Based on my project records, should this work live under [existing-project] or be its own new project? Explain why.

Parallel sessions on the same project

Running 2 Claude Code sessions on the same project folder at the same time?

Works, but be careful

• Both sessions might edit the same files - last write wins, earlier edits lost
• Both can /wrapup, which will write separate session_memories rows (fine)
• Coordinate: have one session doing one thing, the other doing something different

Better pattern for parallel work: separate the project into sub-folders, run one Claude session per sub-folder.

Power-user tips

• End each session with "what's next" - before /wrapup, tell Claude "what would you start with next session?" - Claude's answer becomes a useful pending item
• Cross-project continuation - if you're switching between 2 projects daily, each /wrapup leaves breadcrumbs for the next time you return
• Search by date range - "show me every session last week" - useful for weekly reviews
• Check-in prompts - for long projects, start session with "what's my historical context on this?" - Claude summarises the arc

Action items

☐ Make pending items specific + actionable, not vague

☐ At /startup, ask Claude for the full arc across last 3 sessions

☐ Save project learnings to the project record as you learn them

☐ Practice cross-session search: "when did we decide X?"

☐ For long projects, do a milestone /wrapup at each phase completion

Module complete. Next: Module 07 - GitHub and publishing your work.

Exercises

1. Review the concepts covered in this lesson: Multi-session workflows.
2. Write down your key takeaway from this lesson.
3. Practice running any commands or prompts mentioned above inside your terminal.