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Feature flags

Skill vindreshsingh/engineering-skills/skills/feature-flags

Decouples deploy from release using feature flags — ship code dark, roll out gradually, kill instantly, and remove the flag once it's done. Use when releasing risky or large changes, rolling out by percentage/cohort, delivering A/B variants, or when stale flags are accumulating as debt.From its SKILL.md

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npx -y skills add vindreshsingh/engineering-skills --skill feature-flags

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SKILL.md

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Feature Flags

Deploying code and releasing a feature are different events, and conflating them is why launches are scary. A feature flag separates them: merge and deploy the code dark, then turn it on for 1%, a cohort, or everyone — and turn it off in seconds if it misbehaves, with no rollback deploy. The power comes with a cost: every flag is a branch in your runtime and a line of debt. This skill is how to get the control without drowning in permanent conditional spaghetti.

It's the delivery mechanism the rest of the lifecycle leans on: [[incremental-delivery]] merges work behind a flag, [[experimentation]] uses flags to split variants, and [[launch-readiness]] uses them for gradual rollout and instant kill. Pair with [[observability]] (watch the metric as you ramp) and [[simplify]] (remove the flag when done).

When to Use

  • Releasing a risky or large change you want to deploy before exposing
  • Gradual rollout — percentage ramp, internal-first, beta cohort, region by region
  • Delivering A/B / experiment variants cleanly ([[experimentation]])
  • Needing a kill switch for a dependency-heavy or failure-prone path
  • Trunk-based development — merging incomplete work safely behind a flag
  • Stale flags are piling up and need a cleanup pass

Skip when a change is trivial and safe to ship directly — a flag adds a code path to test and remove; don't flag a typo fix. Don't use flags to avoid ever finishing the work either (see debt below).

Not a substitute for [[launch-readiness]] (the full release gate) or [[migration-path]] (data/contract migration) — flags control exposure; those govern readiness and schema change.

Process

1. Classify the flag — its type sets its lifespan

  • Release flag — hide work-in-progress; short-lived, removed once fully rolled out.
  • Ops / kill switch — disable a risky path under load or failure; long-lived but few.
  • Experiment flag — split variants for [[experimentation]]; removed when the test concludes.
  • Permission / entitlement flag — gate by plan/role; permanent by design, treat as config.

Knowing the type up front tells you when (or whether) it dies. Most pain comes from release flags that never got removed.

2. Name and default safely

Name for intent and direction (enable_new_checkout, not flag2). Default to off / the safe path — a missing or failed flag lookup must fall back to current behavior, never to the half-built new one.

3. Keep the flagged code path testable on both sides

Both states ship in the binary, so both must work. Test flag-on and flag-off paths ([[test-first]]); CI should exercise both. Don't let the off-path rot — it's your rollback.

4. Minimize blast radius and nesting

  • Check the flag at one clear seam, not sprinkled through ten files — wrap the entry point.
  • Avoid nested/combinatorial flags — three interacting booleans is eight untested states. If logic depends on flag combinations, you have a state-machine problem, not a flag.
  • Evaluate flags deterministically per user so a user doesn't flip mid-session ([[experimentation]] needs stable assignment).

5. Roll out gradually with a metric and a kill plan

Ramp deliberately — internal → 1% → 10% → 50% → 100% — watching the primary and guardrail metrics at each step ([[observability]]). Define the kill condition before ramping (error rate, latency, a business metric) and confirm the off-switch actually works. A kill switch you've never tested is a hope, not a control.

6. Govern the inventory

Maintain a registry: each flag's owner, type, default, created date, and expected removal. A flag with no owner is a future incident. Stale release flags are tech debt with a security and correctness cost (dead code paths, surprising states).

7. Remove the flag — this is part of the job, not optional

Once a release flag is at 100% and stable, delete it and the losing code path ([[simplify]]). The task isn't done at full rollout; it's done when the flag is gone. Schedule removal when you create the flag, not "someday." Permanent flags (entitlement, kill switches) are the only ones that stay.

Common Rationalizations

  • "I'll remove the flag later." — "Later" is how a codebase ends up with 200 dead flags; schedule removal when you add it.
  • "Just check the flag wherever I need it." — Scattered checks are untestable and unremovable; gate at one seam.
  • "The off-path won't be used, skip testing it." — The off-path is your rollback; if it's broken you can't kill the feature.
  • "A few nested flags are fine." — N flags = 2^N states; nobody tests them all. Collapse to explicit states.
  • "Default it on so people see the new thing." — A failed lookup then serves half-built code; default to the safe path.
  • "Flags let us skip the release gate." — Flags control exposure, not readiness; [[launch-readiness]] still applies.

Red Flags

  • Release flags with no owner or removal date in any registry
  • The same flag checked in many scattered places
  • Nested/combinatorial flags creating untested state combinations
  • Flag defaults to the new/unsafe behavior on lookup failure
  • Off-path (rollback) untested or rotted
  • Kill switch never actually exercised
  • Flags used as permanent forks instead of being removed after rollout
  • 100%-rolled-out flags still in the code months later

Verification

  • Flag type classified (release / ops / experiment / permission) with a matching lifespan
  • Named for intent; defaults to the safe/current path on missing-or-failed lookup
  • Both flag-on and flag-off paths tested in CI ([[test-first]])
  • Evaluated at one clear seam; no nested/combinatorial flag logic; stable per-user assignment
  • Gradual rollout plan with primary + guardrail metrics and a pre-defined, tested kill condition
  • Registry entry: owner, type, default, created and expected-removal dates
  • Release/experiment flags removed (with dead path) after rollout/conclusion ([[simplify]])

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