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Description
Problem
When working on Squad from source, the .ai-team/ directory was hand-created early in development and has drifted from what squad init produces for customers. There's no way to refresh the source repo's team config without manually editing files.
More broadly, any long-running Squad project accumulates drift between its .ai-team/ state and the latest templates — missing role icons, outdated charter sections, stale formatting.
Proposal: squad upgrade --self
A new CLI flag that refreshes the current repo's .ai-team/ files to match current templates without losing custom content.
What it refreshes:
team.md:
- Add role emoji icons to roster if missing
- Update @copilot capabilities section to match
templates/roster.md - Normalize coordinator name to "Squad"
- Preserve all custom members, project context, and board config
Charters (.ai-team/agents/*/charter.md):
- Ensure all standard sections exist (Identity, What I Own, How I Work, Boundaries, Model, Collaboration, Voice)
- Add missing sections from
templates/charter.mdwith sensible defaults - Never overwrite existing custom content in any section
- Report which charters were updated and what sections were added
Structural files:
- Ensure
ceremonies.md,routing.md,decisions.mdexist - Ensure
casting/,skills/,orchestration-log/,log/,decisions/inbox/dirs exist - Ensure
.gitattributeshas themerge=uniondrivers
What it does NOT touch:
- history.md files (agent memory — never modified by upgrade)
- decisions.md content (append-only ledger)
- Agent names (casting is permanent)
- Any custom sections agents have added to their charters
UX:
$ npx github:bradygaster/squad upgrade --self
Refreshing .ai-team/ to match current templates...
team.md — added role icons to 9 members
keaton/charter.md — added missing Model section
fenster/charter.md — up to date
ceremonies.md — up to date
.gitattributes — added merge=union drivers
Self-upgrade complete. 2 files updated.
Why this matters
- Dogfooding — Brady and the squad squad get the latest UX automatically
- Customer value — any long-running project benefits from template improvements
- Meta-delightful — updating Squad inside of Squad is peak Squad
Acceptance Criteria
-
squad upgrade --selfflag implemented in index.js - Refreshes team.md formatting (icons, structure) without losing custom content
- Adds missing charter sections without overwriting existing ones
- Ensures structural directories and files exist
- Reports what was changed
- Tests covering the refresh behavior
- Works when run from the source repo itself
Activity
bradygaster commentedon Feb 16, 2026
✅ Implemented in latest commit. squad upgrade --self now refreshes squad repo's own .ai-team/ from templates while preserving agent histories.
feat: complete v0.4.1 blockers (#70, #68, #67)
docs(ai-team): spike research — 6 spikes completed with findings post…
Merge pull request github#68 from jbenami_microsoft/squad/18-squad-te…