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[EPIC] v0.5.0 — .squad/ Migration & Architectural Cleanup #91

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@bradygaster

v0.5.0 — Last Breaking Change Before v1.0

Timeline: Feb 17 - Mar 16, 2026 (4 weeks)
Release Date: March 16, 2026
Status: In Progress (Week 1 Day 2)

Breaking Change

Primary: Consolidate to single .squad/ directory (#69)

  • .ai-team/ → .squad/
  • .ai-team-templates/ → .squad/templates/ (nested)
  • ~1,672 occurrences across 130+ files
  • Mandatory migration via squad upgrade --migrate-directory
  • Backward compatibility window: v0.5.0 → v1.0.0
  • Full legacy removal: v1.0.0

Rationale: One folder to find, one folder to .gitignore, one folder to understand. No confusion about where Squad state lives.

MUST Ship Issues

Issue Title Owner Estimate
#69 Consolidate to .squad/ (directory + templates) Fenster 85h
#76 Refactor squad.agent.md for GHE 30KB limit Verbal 24h
#86 Squad undid uncommitted changes (HIGH SEVERITY) Fenster + Hockney 6-12h
#71 Cleanup label workflows Fenster 18h
#84 Add timestamps to session logs Fenster 12h
#62 CI/CD integration patterns Kobayashi 28h

Total Core: ~173-179 squad-hours

Bundled Enhancements

PR Title Status Shipped
#80 Add llms.txt outputs to docs build ✅ Merged to dev Feb 17
#89 Fix MCP Discord notifications setup docs ✅ Merged to dev Feb 17

Both ride with v0.5.0 release March 16.

Launch Features

Insider Program (Week 1 Priority)

Binary access model: Insider (continuous dev/nightly) or Release (stable).

WHY FIRST: Testing infrastructure enables incremental validation throughout sprint. Contributors test #69, #76, #86 fixes as they merge to dev, not waiting until Week 3 beta.

Installation:

  • Regular: npx github:bradygaster/squad
  • Insider: npx github:bradygaster/squad#insider
  • Upgrade: squad upgrade supports regular → insider switching

Architecture:

  • Separate insider branch ("dev minus the team state")
  • Isolated state: .squad-insider/ directory
  • Version: v0.5.0-insider+{commit} for bug reporting
  • Honor-system access + public list in CONTRIBUTORS.md

No rings, no caps: Everyone who contributes meaningfully can be an insider.

Recognition: [INSIDER] badge in CONTRIBUTORS.md, Discord #squad-insiders channel, blog credits, release notes.

Responsibilities: Test within 48-72h, file detailed bugs, validate exit criteria (optional).

Supporting Initiatives

Blogging (McManus)

Target: 4 blog posts during v0.5.0 cycle

  1. Week 1 (Feb 20-21): v0.5.0 kickoff — insider program opens, migration preview, Squad undid its own uncommited changes from a previous session #86 findings
  2. Week 2 (Feb 27-28): Under the hood — squad.agent.md split (Squads in GitHub Enterprise Copilot- Invalid config "Prompt" exceeds max length 30000 #76), single-folder rationale
  3. Week 3 (Mar 6-7): Insider testing — early signals, migration feedback
  4. Week 4 (Mar 16): v0.5.0 ships — migration guide, insider invitation confirmation, Squad undid its own uncommited changes from a previous session #86 fix announcement

Architectural Analysis (#86 & #87)

Decision (Feb 16, comment #3911872475):

Deferred to v0.6.0

Issue Title Rationale
#63 Review label taxonomy Post-migration polish
#82 Session log compression Performance optimization
#85 Skill confidence auto-bump Intelligence enhancement
#36 JetBrains + GitHub.com research After VS Code parity (#32-35)
#79 Historical decision search Discovery feature
#87 Workflow project type detection Template polish, not blocker
#75 Agent spawning metrics Observability

Mandatory Beta Program

Cohort size: 5-10 users
Duration: Week 3-4 (Mar 3-16)
Target: Power users, existing contributors, early adopters

Exit criteria (all required):

  1. Migration succeeds on 5 real repos (with existing .ai-team/ state)
  2. Zero state corruption reports
  3. Upgrade path tested (v0.4.1 → v0.5.0)
  4. Workflows pass on migrated repos
  5. Documentation validates (migration guide, troubleshooting)
  6. Squad undid its own uncommited changes from a previous session #86 fix validated (no more uncommitted work loss)
  7. Performance acceptable (no >10% overhead vs v0.4.1)

Timeline

Week 1 (Feb 17-23): Insider Program + Critical Investigation

PRIMARY: Insider Program infrastructure (enables incremental testing)

  • Set up insider branch + CI/CD automation
  • Document install paths (regular vs insider)
  • CONTRIBUTORS.md badge system
  • Discord #squad-insiders channel setup
  • First insider publish (v0.5.0-insider+{commit})

SECONDARY: Critical bug investigation

Blog post #1 (Feb 20-21): v0.5.0 kickoff — insider program opens NOW

Week 2 (Feb 24 - Mar 2): Implementation Wave 1

Week 3 (Mar 3-9): Implementation Wave 2 + Beta Testing

Week 4 (Mar 10-16): Final Wave + Release

Success Criteria

Week 1 Day 2 Progress (Feb 18)

Completed:

In Progress:

Next:

Communications

  • Insider Program: Binary model (insider or release), launches Week 1 for incremental testing
  • Migration: Single .squad/ folder, mandatory but supported, backward compat until v1.0.0
  • Squad undid its own uncommited changes from a previous session #86 fix: Trust signal — Squad protects your work (prompt-only, 3-4h, ships v0.5.0)
  • Last breaking change: v1.0.0 will be polish, not breaking

Note: This is the last breaking change before v1.0.0. Post-v0.5.0 releases focus on stability, polish, and feature additions without migration pain.

Activity

  1. added this to the v0.5.0 milestone on Feb 17, 2026
  2. bradygaster commented on Feb 17, 2026

    @bradygaster
    CollaboratorAuthor

    🎯 Insider Program & Release Cadence (PERMANENT INFRASTRUCTURE)

    v0.5.0's mandatory beta program revealed the need for ongoing testing infrastructure with predictable release cadence. Three-agent consultation (Keaton: program structure, McManus: community engagement, Kobayashi: release automation) designed permanent systems.

    Program Overview

    Squad Insiders — 5-10 (growing to 20+) experienced users who test pre-releases 7-10 days before public ship, validate exit criteria, and give structured feedback.

    Benefits:

    • Early access (pre-release builds 3-7 days before GA)
    • Recognition (CONTRIBUTORS.md, CHANGELOG credits)
    • Direct line (#squad-insiders Discord, fast-tracked issues)
    • Influence (roadmap voting, design feedback sessions)

    Commitment:

    • Breaking-change releases: Test within 48-72h, validate 1-2 assigned exit criteria (2-4 hours per release)
    • Minor releases: Optional participation
    • No code contributions required (valued but not mandatory)

    Entry paths:

    1. Invitation (Lead/DevRel invite based on production usage, contributions, technical depth)
    2. Application (open via GitHub Discussions, rolling acceptance)
    3. Auto-qualify (3+ merged PRs, significant contribution)

    Exit: Opt-out anytime (no penalty). Inactive for 3+ releases → alumni status (keep Discord, lose early builds, can rejoin).

    v0.5.0 Integration

    Beta testers become inaugural insiders. At v0.5.0 ship (March 16), invite each beta tester to join permanent program. Opt-in, same access/feedback loop, now ongoing.

    Cohort growth: Start 5-10 (v0.5.0), add 3-5 per major release, cap at ~30.

    Release Cadence

    Pre-1.0 (Current):

    • Milestone-driven with 4-6 week time caps
    • Breaking changes: 2-week insider beta (e.g., v0.5.0 directory rename)
    • Patches: 1-3 day express lane (skip insider testing)

    Post-1.0 (Future):

    • Biweekly releases (every 2 weeks, Fridays)
    • Predictable rhythm builds user trust
    • Milestone overflow rolls to next release (no rush pressure)

    Three-Tier Testing Process

    Tier Scope Process Gate
    Tier 1: Patches Bug fixes, docs, non-breaking CI + smoke test, 1-3 days CI green
    Tier 2: Minor New features, additive changes CI + 1-week insider beta + 6 exit criteria 80% success, zero P0 bugs, docs complete, GHE validated, cross-platform
    Tier 3: Breaking Breaking changes, migrations CI + 2-week insider beta + 7 exit criteria 90% success, zero corruption, rollback tested, migration guide documented

    Automation Roadmap (3 Phases)

    Phase 1 (v0.5.0 — Build Now):

    • Pre-release tags (v0.5.0-beta.1, v0.5.0-beta.2)
    • Discord webhooks (auto-post when beta tag created)
    • Exit criteria template (GitHub Issue with checklist)

    Phase 2 (v0.6.0 — Post-Beta Learnings):

    • Migration smoke tests (CI validates upgrade path)
    • Multi-repo test matrix (small/medium/large/mono/multilang fixtures)
    • Feedback collection bot (parse Discussions, auto-update exit criteria)

    Phase 3 (v1.0.0 — Polish for Production):

    • Automated release notes (generate from git log + closed issues)
    • One-click beta promotion (promote to stable when exit criteria met)
    • Health dashboard (install count, upgrade success rate, issue velocity)

    Community Engagement

    Recruitment:

    • Seed cohort (direct outreach to @spboyer, @londospark, @miketsui3a, Jeff Fritz) by March 1
    • Open applications via GitHub Discussions (rolling acceptance, 3-5 day response time)
    • Organic growth (auto-invite after 3+ PRs or 5+ quality issues)

    Recognition:

    • Public credits in release notes and CONTRIBUTORS.md
    • Private Discord channel (#squad-insiders)
    • Blog posts for significant contributions
    • No swag until cohort stabilizes above 20 (deferred to v0.7.0+)

    Communication:

    • Discord #squad-insiders: real-time feedback, Q&A, pre-release announcements
    • GitHub Discussions: formal feedback threads, structured discussions (public for transparency)
    • Direct issues with insider-feedback label: blockers, urgent feedback
    • Monthly check-in threads, quarterly retrospectives

    Onboarding:

    • Welcome package: Insider Playbook, core team intros, first mission (install + report within 7 days)
    • Exit criteria reference (link to v0.5.0 exit criteria as example)
    • Clear opt-out policy (no penalties, alumni tier for graceful exits)

    Implementation Timeline

    Phase Deliverable Target Date
    Recruit seed cohort 10 insiders via direct outreach March 1
    Create infrastructure Discord channel, GitHub Discussions category, insider playbook March 5
    v0.5.0 beta testing Insiders test pre-release (7 days) March 9–16
    Public launch Open applications, publish docs, add README badge March 16 (release day)
    First monthly check-in Establish cadence April 1
    First quarterly retro Structured feedback for v0.6.0 planning June 1

    Success Metrics

    Recruitment: 10 by March 1, 20 by June 1, 50 by December 1

    Engagement: 70%+ test each pre-release, 5+ actionable feedback per release, 50%+ quarterly retro participation

    Recognition: 100% insiders credited in release notes, 3+ insider blog posts by EOY

    Retention: <30% churn per quarter, alumni tier prevents hard drop-off

    Open Questions for Brady

    1. Discord vs Discussions for #insiders? (Recommendation: Discord for Q&A, Discussions for structured feedback)
    2. Public vs private insider list? (Recommendation: Public in CONTRIBUTORS.md for recognition)
    3. Monetary thank-you for v1.0.0 validation? (Recommendation: Nice but not required, defer to v1.0.0)
    4. Invite existing contributors as insiders retroactively? (Recommendation: Yes — Shayne Boyer, Anton Molchanov auto-qualify)
    5. Share Horizon roadmap with insiders? (Recommendation: Yes, async written format only)

    This infrastructure makes Squad's beta testing repeatable, scales from solo maintainer to distributed team, and creates a contributor pipeline: insiders → contributors → maintainers.


    Full Recommendations:

    • Keaton (Program Structure): .ai-team/decisions/inbox/keaton-insider-program-structure.md
    • McManus (Community Engagement): .ai-team/decisions/inbox/mcmanus-insider-community-engagement.md
    • Kobayashi (Release Cadence): .ai-team/decisions/inbox/kobayashi-release-cadence-testing.md
  3. bradygaster commented on Feb 17, 2026

    @bradygaster
    CollaboratorAuthor

    📦 Shipped Enhancement — PR #80

    docs: add llms.txt outputs to docs build (merged Feb 17 by @danielscholl)

    Adds LLM-discoverable documentation outputs:

    • llms.txt — curated docs index (pages LLMs should prioritize)
    • llms-full.txt — full corpus export (all Squad docs in one file)
    • *.html.md — markdown companions aligned to rendered page URLs

    Why it ships with v0.5.0: Enhances discoverability for AI tooling that wants to learn Squad. Low-risk documentation enhancement, already merged and tested.

    Implementation: Updated docs/build.js with shared frontmatter stripping helper, clean snippet extraction for readable descriptions.

  4. bradygaster commented on Feb 17, 2026

    @bradygaster
    CollaboratorAuthor

    📦 Shipped Enhancement — PR #89

    fix: mcp discord notifications setup instructions (merged Feb 17 by @digitaldrummerj)

    Fixes Issue #88 (Discord docs outdated) - updates MCP Discord notification setup instructions.

    Impact on v0.5.0 scope: Removes #88 from deferred list - already fixed by community contribution. One less item to carry into v0.6.0.

  5. bradygaster commented on Feb 17, 2026

    @bradygaster
    CollaboratorAuthor

    🔍 Architectural Analysis: Issues #86 and #87

    ✅ Issue #86: Data Loss Bug (CONFIRMED HIGH SEVERITY — Stay in Scope)

    Root cause: Prompt engineering failure — agents lack git discipline. When hitting errors, agents use git checkout to undo without checking for other uncommitted changes → wipes out prior work from same session.

    NOT migration-related. This bug exists in v0.4.1 right now. Directory rename has zero impact on git operations.

    Action plan:

    • Week 1 investigation (already planned ✅)
    • If fix is prompt-only (add git safety checks to spawn templates, 2-4h) → bundle into v0.5.0
    • If fix requires complex tooling (8-12h) → defer to v0.5.1 patch
    • Gate: Validate across 3-4 "agent errors and tries to undo" scenarios before ship

    ❌ Issue #87: Workflows Assume npm (Stay Deferred to v0.6.0)

    Root cause: Template generation doesn't detect project type. Squad was built FOR Squad (npm), so templates reflect that. Non-npm projects (Python, .NET, Java, Go) hit wrong assumptions.

    Architectural verdict: NOT architectural. Doesn't affect Squad's core (agents, memory, coordinator) — it's template polish.

    Why defer:

    1. Scope protection — v0.5.0 is 242h. Project type detection adds +16-22h (6-8% timeline increase)
    2. Risk mismatch — v0.5.0 risk is state corruption (catastrophic). squad- workflows seem to assume a particular project type? #87 risk is "wrong template" (annoying but 10-second workaround)
    3. Beta complexity — Would require multi-language cohort vs. focused migration testing
    4. Natural v0.6.0 fit — Polish release after the last breaking change

    If pulling into v0.5.0: Add 2 weeks to timeline (Mar 16 → Mar 30), recruit multi-language beta, accept diluted feedback. Not recommended.


    Summary

    Issue Include? Why Effort
    #86 ✅ YES (conditional) Trust-destroying data loss — already planned 6-12h
    #87 ❌ NO Template polish — not architectural 16-22h

    v0.5.0 scope unchanged. Existing plan is correct.

  6. bradygaster commented on Feb 20, 2026

    @bradygaster
    CollaboratorAuthor

    v0.5.0 Sprint Complete ✅

    All work items shipped:

    Issue Work PR
    #71 Remove .ai-team/ deprecation banner from squad.agent.md #115
    #98 Extract cold-path sections (context pressure reduction) #114
    #84 Standardize ISO 8601 timestamps #117
    #85 Decision lifecycle management SKILL.md + archival #118
    #82 Skills export/import verification + docs + tests #119
    #62 Version bump 0.5.0 + CI validation + release checklist #120
    #107 Identity layer (wisdom.md + now.md) #121
    #108 Email scrub tests #122
    #106 Verify .squad/ guard workflow blocking closed (already resolved)
    #76 squad.agent.md token count check closed (under GHE limit)

    Final test count: 64/64 passing on dev.

    v0.5.0 ready for release merge (dev → preview → main).

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