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[PF-1992] Migration orchestrator#4946

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[PF-1992] Migration orchestrator#4946
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feature/pf-1992-migration-orchestrator

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@vedrani vedrani commented May 8, 2026 •
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PF-1992

PF-1992 — Migration orchestrator + supporting docs

Closes the PF-1992 ticket: ships the autonomous-migration orchestrator, gate scripts, diff helpers, locked decision docs, per-component plan files, prompt pack, manifest, and reference materials for the upcoming PF-1994 / PF-2024 / PF-2025 / PF-2020-2023 batches.

TL;DR

A workflow-agnostic orchestrator that drives Claude Code subprocess invocations through a 14-step per-component loop: agent migrates source → gate (build/tsc/lint/jest/cypress/happo) → push → poll CI → classify failures → auto-fix or feed-to-agent → on green flip to awaiting_review → separate --review-sweep mode handles human reviews on its own cadence. Validated by 12+ canaries on Note + Form + Container + Button across the Tier 0/1 surface; per-canary cost ~$0.30-1.00 in Anthropic API.

The orchestrator is single-workflow today (migration); the Workflow interface is built for extension to future workflows (Figma → component, bug-fix, etc.) without touching the core loop.

This PR is infrastructure-only. Per-component migrations land as separate PRs against feature/picasso-modernization (already created), driven by yarn orchestrate.

Scope

Surface Files LOC
Orchestrator core (loop, state machine, retries, sweep, locks) bin/lib/orchestrator-core.ts ~3,000
Workflow descriptor interface bin/lib/workflow.ts ~400
Failure classifier (CI failure → action) bin/lib/failure-classifier.ts ~300
Review classifier (PR comments → action) bin/lib/review-classifier.ts ~300
Token telemetry (cost.json per canary) bin/lib/token-telemetry.ts ~250
Migration workflow descriptor + entrypoint bin/migration-orchestrator.ts ~270
Gate script (build/tsc/lint/jest/cypress/happo strict gate) bin/migration-gate.sh ~470
Diff helper (prop-surface + import + happo summary) bin/migration-diff.sh ~260
classes prop compatibility shim packages/base/Utils/src/utils/with-classes.ts + tests ~130
Manifest (28 component-migration units) docs/migration/manifest.json + schema ~400
Per-component plans (Tier 0 + Tier 1) docs/migration/components/*.md ~700
Locked decision docs docs/migration/decisions/*.md ~700
Agent prompts (light + heavy paths) docs/migration/PROMPT-*.md ~350
Rules (api-preservation, styling, JSS crib, base-ui-react crib) docs/migration/rules/*.md ~600
Token reference docs/migration/tokens/picasso-tailwind-tokens.md ~150
References (agent-loop, escalation, PR workflow, lessons) docs/migration/references/*.md ~500
Runbook docs/migration/ORCHESTRATOR.md ~300

Total: ~5,400 LOC (code) + ~3,500 LOC (markdown docs). Most documentation files are templated content, not contentious code.

Reviewer guide — what to read in what order

This PR is large but has a clear priority hierarchy. Pick a slice based on your role; you don't need to read everything.

Highest value (please review thoroughly)

Engineering reviewer — focus here:

  • bin/lib/orchestrator-core.ts — the 14-step run() loop, runBatch, runReviewSweep + sweepOne, Phase 3.3 CI iteration, workspace-overlay fix, per-item locks.
  • bin/migration-gate.sh — gate stage flow + the new strict Happo REST API gate (per migration plan v4 §6.3).
  • bin/lib/failure-classifier.ts — pure-function CI-failure classifier; 10-step heuristic decision tree.
  • bin/lib/review-classifier.ts — pure-function review classifier with confidence scoring.
  • packages/base/Utils/src/utils/with-classes.ts — classes prop compatibility shim (consumer-API impact across 23 downstream repos).

Domain / Picasso reviewer — focus here:

  • docs/migration/decisions/ (4 docs):
    • backdrop-replacement.md — custom <div> + scroll-lock (no @base-ui/react analog)
    • popper-replacement.md — @floating-ui/react direct dependency (preserves position-anchored API)
    • classes-shim.md — Tailwind-routing shim policy (walks back v3-era "remove classes" plan)
    • integration-branch.md — feature/picasso-modernization long-lived branch
  • docs/migration/components/*.md — 19 per-component plan files. Slot-keys section is canonical for the upcoming agent runs; corrections welcome.
  • docs/migration/PROMPT-light.md + PROMPT-heavy.md — agent system prompts. Tier 0 (light) = @mui/base → @base-ui/react package swap; Tier 1+ (heavy) = full rewrite.
  • docs/migration/manifest.json — 28 component-migration units across 6 tiers per migration plan v4 §3.9.

Designer — review one Tier 0 canary PR's Happo diffs once those land (intentional pixel changes from MUI v4 → @base-ui/react DOM cleanup are expected).

Medium value (skim)

  • bin/lib/workflow.ts — Workflow descriptor interface. Note: critique flagged this as premature abstraction (only 1 consumer today). Documented decision: leave as-is until 2nd workflow lands; inline post-migration if no 2nd workflow surfaces.
  • bin/lib/orchestrator-core.ts — retry logic for gh.viewPR / gh.createPR / gh.fetchJobLog (3 similar 4-attempt exp-backoff blocks), Phase 3.3 iteration loop, token telemetry hooks, .envrc auto-load.
  • bin/lib/token-telemetry.ts — reads Claude Code session jsonl (~/.claude/projects/<encoded-cwd>/<session-id>.jsonl), aggregates token usage, computes USD estimates at Sonnet 4.5 list pricing, writes migration-runs/<date>/<id>/cost.json.
  • docs/migration/rules/api-preservation.md — preserved classes prop policy (per migration plan v4 §2.3).

Lowest value (template / reference)

  • bin/migration-diff.sh — diff snapshot/report shell helper.
  • docs/migration/tokens/picasso-tailwind-tokens.md — token reference (auto-generated content).
  • docs/migration/rules/jss-to-tailwind-crib.md + styling.md — JSS → Tailwind transformation table.
  • docs/migration/references/lessons-learned.md — auto-accumulated by the orchestrator post-each-successful-PR; will grow during PF-1994.

Architecture decisions (locked, May 2026)

Per docs/modernization/PI-4318-PF-1992-design-decisions.md + migration plan v4. Each has a decision doc:

Decision Doc Rationale
Long-lived feature/picasso-modernization integration branch (renamed from picasso-modernization to fit Picasso CI's master + feature/** trigger config) decisions/integration-branch.md Single revertible point per tier; master stays clean of half-migrated state
Backdrop replacement = custom <div> + Tailwind + scroll-lock decisions/backdrop-replacement.md No standalone Backdrop in @base-ui/react; preserves external consumer API
Popper replacement = @floating-ui/react direct dep decisions/popper-replacement.md @base-ui/react/popover is trigger-anchored; would force every consumer to refactor
classes prop preserved via Tailwind-routing shim decisions/classes-shim.md Walks back v3-era "remove classes" plan; preserves ~80% of consumer usage in 23-repo portfolio
Strict Happo gate (zero-diff OR designer-accepted via REST API) (lives inline in bin/migration-gate.sh; design captured in migration plan v4 §6.3) Catches real visual regressions vs. flake retries
Async review sweep (decoupled from migrate-mode) (in-code design comment in bin/lib/orchestrator-core.ts) Operator review cadence is hours-to-days; sync wait blocks orchestrator
Per-item file locks at migration-runs/.locks/<id> (stale-PID detection) (in-code) Prevents concurrent migrate vs. sweep collisions
Token telemetry per canary (in-code) Operator visibility into per-component / aggregate spend

Validation evidence

The orchestrator is validated end-to-end by 12+ canary runs on Note (sandbox), Form, Container, and Button against feature/picasso-modernization:

Path Validated by Evidence
Inner gate loop (build → tsc → lint → jest → cypress → happo → react19) All canaries 18-29 migration-runs/<date>/<id>/report.json
--batch multi-component sequential Validate C [batch] [1] ... [batch] [2] ... [batch] --max-items=2 cap reached
Phase 3.3 CI iteration (auto-fix-snapshot + feed-to-agent) Canary 19 / 20 / 28 Auto-regenerated Pagination snapshots when Tier 0 ripple hit consumer packages
Workspace overlay (Phase 2.5b) Canary 22+ Consumer-package tests now resolve to worktree's source, not main repo's
Async sweep + per-item locks Smoke-tested via dry-run + --review-sweep no-work [sweep] no items in awaiting_review state — nothing to sweep
Token telemetry Canary 29 + Validate C Form: $0.54; Container: $0.41; Form (re-run): $0.24
Resilience (5xx retries, spending-cap detect, 60s post-push sleep) Canaries 25-29 Each surfaced + fixed a distinct latent bug
Strict Happo gate Smoke-tested at gate-stage level (not yet end-to-end on a real diff — needs Day 2 Tier 1 to fully exercise) (Schema TBD — relies on Happo REST API shape; fall-through to PASS on shape mismatch)

Out of scope (separate tickets)

  • TypeScript 5.5/5.6 upgrade (migration plan v4 §9.1) — separate parallel ticket; PF-1994 cannot start until both PF-1992 + the TS ticket land.
  • Pipelined state-machine refactor (v4 Step 2) — current sequential --batch is adequate for one operator + Anthropic singleton; revisit post-migration if parallelism is needed.
  • Slack webhook (v4 Step 3) — ergonomic polish, not load-bearing; deferrable.
  • Codemod authoring for breaking-change props (@toptal/picasso-codemod v53+) — feeds PF-1995.
  • Tier 4 sibling packages (charts, query-builder, RTE) — PF-2020/2021/2022.
  • Tier 5 provider runtime (Picasso Provider rewrite + root peer-dep removal) — PF-2023.
  • picasso@next dist-tag publishing during Phase 2 — design decision §9.9 still open.

Known critique acknowledgments (deferred refactors)

A fresh-eyes architectural review surfaced four legitimate over-engineering hotspots. Each is left as-is for this PR because none ship migration value and all are low-risk to defer:

  1. Workflow interface (bin/lib/workflow.ts) — premature abstraction with one consumer (migration). Inline as MigrationWorkflow post-migration if no 2nd workflow lands.
  2. Three duplicate gh.* retry loops (createPR, viewPR, fetchJobLog) — collapse to a withRetry<T> helper. Cosmetic refactor; ~40 LOC saved.
  3. --with-mcp flag (Playwright integration) never validated by any canary. Documented as experimental; enable for first Tier 2/3 component.
  4. Token-telemetry's cache-tier breakdown (5m vs 1h) is informational; could slim to { iteration, costUsd } per snapshot.

Verification — how to test this PR locally

Prerequisites

  • Node 20+, Yarn 1.22.x, gh CLI authenticated, Claude Code logged in (claude subprocess auth lives in ~/.claude/).
  • direnv with ~/Projects/.envrc exporting HAPPO_API_KEY + HAPPO_API_SECRET (or equivalent shell env). Orchestrator auto-loads from .envrc if direnv hook isn't active.

Smoke tests (no API spend)

# Dry-run plan output for any Tier 1 component
yarn orchestrate --component=Form --no-merge --dry-run

# Sweep with no awaiting_review items → no-op
yarn orchestrate --review-sweep

# `--max-items=N` flag
yarn orchestrate --tier=1 --batch --no-merge --max-items=2 --dry-run

# `withClasses` shim unit tests
yarn jest packages/base/Utils/src/utils/__tests__/with-classes

Real canary (~$0.30-0.50, ~12 min wall-clock)

# Pick a Tier 1 already-clean component and run end-to-end
yarn orchestrate --component=Note --no-merge --max-iterations=5 --ci-timeout-minutes=25

Watch the log for:

  • [loop] selected: Note (tier=1, status=queued, ...)
  • [loop] gates pass on iteration 1
  • [cost] iter 1: total $0.NN (in=N, out=N, cache_read=N)
  • [loop] polling CI on https://github.com/toptal/picasso/pull/<N>
  • All checks green except possibly Happo (Picasso/Cypress) — known flake on Tier 1; designer-accept in Happo UI to clear

After completion, check:

  • migration-runs/<date>/Note/cost.json — per-iter token + USD breakdown
  • migration-runs/<date>/Note/report.json — structured gate report
  • docs/migration/manifest.json — Note.status should be awaiting_review

Verification of decision docs

Each decision doc is internally consistent and matches the in-code implementation:

  • decisions/backdrop-replacement.md ⟷ Backdrop's target_path: 'none' in manifest
  • decisions/popper-replacement.md ⟷ Popper's plan file in components/Popper.md
  • decisions/classes-shim.md ⟷ packages/base/Utils/src/utils/with-classes.ts implementation
  • decisions/integration-branch.md ⟷ migrationWorkflow.baseBranch in bin/migration-orchestrator.ts

Test plan

  • yarn workspace @toptal/picasso-utils build:package (compiles withClasses + tests)
  • yarn jest packages/base/Utils/src/utils/__tests__/with-classes.test.ts (8/8 passing)
  • yarn typecheck (full repo)
  • yarn eslint --ext=.ts bin/ (0 errors; warnings are pre-existing or acceptable)
  • yarn orchestrate --component=Note --dry-run (planned 14 steps print correctly)
  • yarn orchestrate --review-sweep (no-op when no awaiting_review items)
  • At least 1 reviewer reads decisions/*.md and confirms each decision matches the in-code implementation
  • At least 1 reviewer skims a Tier 1 plan file (e.g. Note.md) + a Tier 0 plan file (e.g. Button.md) to verify Slot keys + acceptance criteria are sensible
  • At least 1 reviewer skims bin/lib/orchestrator-core.ts:run() flow

Follow-ups (separate PRs after this lands)

  1. Day 2 Tier 1 batch (PF-1994) — process all 11 Tier 1 cleanup-only / type-only-fix components via yarn orchestrate --tier=1 --batch --no-merge.
  2. Day 3 Tier 0 batch (PF-1994) — 8 components in dependency order: Backdrop → Badge → Button → Slider → Switch → Tabs → Modal → Drawer.
  3. Day 4+ Tier 2 / Tier 3 (PF-2024 / PF-2025) — heavy migrations one at a time with operator review.
  4. Sweep cron — */30 * * * * yarn orchestrate --review-sweep (or operator-driven cadence).
  5. Critique simplifications (post-migration) — collapse gh.* retries, inline Workflow, slim telemetry.

Acknowledgments

  • Migration plan v4 + design decisions per docs/modernization/PI-4318-P1-MOD-01-migration-plan.md + PI-4318-PF-1992-design-decisions.md.
  • PR [TAPS-0000] Migrate Button and Switch to BASE UI #4906 (Button + Switch on @base-ui/react) — the calibration baseline for Tier 0 light path.
  • Canaries 18-31 series — each surfaced a distinct latent bug; full per-canary log in migration-runs/.

Refs: PF-1992

How to test

  • Temploy
  • FIXME: Add the steps describing how to verify your changes

Screenshots

Before. After.
Insert screenshots or screen recordings Insert screenshots or screen recordings

Development checks

  • Add changeset according to guidelines (if needed)
  • Double check if picasso-tailwind-merge requires major update (check its README.md)
  • Read CONTRIBUTING.md and Component API principles
  • Make sure that additions and changes on the design follow Toptal's BASE design, and it's been already discussed with designers at #-base-core
  • Annotate all props in component with documentation
  • Create examples for component
  • Ensure that deployed demo has expected results and good examples
  • Ensure the changed/created components have not caused accessibility issues. How to use accessibility plugin in storybook.
  • Self reviewed
  • Covered with tests (visual tests included)

Breaking change

  • codemod is created and showcased in the changeset
  • test alpha package of Picasso in StaffPortal

All development checks should be done and set checked to pass the
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@vedrani vedrani requested a review from a team as a code owner May 8, 2026 06:25
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🦋 Changeset detected

Latest commit: 77da53c

The changes in this PR will be included in the next version bump.

This PR includes changesets to release 85 packages
Name Type
@toptal/picasso-shared Minor
@toptal/picasso Patch
@toptal/picasso-autocomplete Patch
@toptal/picasso-avatar Patch
@toptal/picasso-avatar-upload Patch
@toptal/picasso-badge Patch
@toptal/picasso-breadcrumbs Patch
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@toptal/picasso-checkbox Patch
@toptal/picasso-environment-banner Patch
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@toptal/picasso-skeleton-loader Patch
@toptal/picasso-slider Patch
@toptal/picasso-step Patch
@toptal/picasso-switch Patch
@toptal/picasso-table Patch
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@toptal/picasso-test-utils Patch
@toptal/picasso-timeline Patch
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vedrani added 28 commits May 11, 2026 17:24
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dulishkovych and others added 5 commits June 15, 2026 13:03
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Record Tooltip v1/v2 run state + audit notes (#5007)
7cc14df 
Merge local Tooltip run state into the manifest, preserving the existing
`vedrani` variant (needs_human, escalated after 10 iters) and adding:
  - v1: in_progress (interrupted local attempt, no PR)
  - v2: awaiting_review, PR #5005 (migrate-Tooltip-v2)

PR #5005's branch was rebased clean onto the migration target (the
14-commit worktree-fork pile was stripped), so v2 now tracks a
Tooltip-only diff. Append the three Tooltip audit sections to
lessons-learned.md (run was interrupted before the auto-append ran).

Refs: PF-1992
@dulishkovych
Record Dropdown v2 run state (PR #5008)
3b01ce2 
Add the Dropdown v2 variant to the orchestrator manifest so a
`--review-sweep` from this branch picks up PR #5008 (migrate-Dropdown-v2).

Status recorded as awaiting_review (the local run left it stale at
in_progress; PR #5008 is OPEN, CI-green, REVIEW_REQUIRED). The branch was
rebased clean onto the migration target (worktree-fork pile stripped), so
v2 tracks a Dropdown-only diff (7 files).

Refs: PF-1992
@vedrani
Fix + Progress
a2a8dfb
@vedrani
Fix cleanup bug
35e69db
@vedrani
Progress + graduation
77da53c
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