Deployment strategy

Skill vignesh2027/AI-AGENT-SKILLS/skills/deployment-strategy

Turn your ai agent into senior engineer..The result is fast code that fails slowly. AI Agent Skills solves this by giving agents the same disciplined workflows senior engineers use

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npx -y skills add vignesh2027/AI-AGENT-SKILLS --skill deployment-strategy

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Deploy with rollback plans, staged rollouts, and feature flags

SKILL.md

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Overview

Deployments fail. The question is not whether, but whether you can recover quickly. This skill makes deployments reversible, observable, and gradual.

When to Use

Before every production deployment
When designing a deployment pipeline
When a deployment caused a production incident
As part of the /ship workflow

Process

Step 1: Write the rollback procedure first

Before deploying, document how to roll back. If you can't write the rollback procedure, you're not ready to deploy.

Step 2: Define the rollout stages

1% → 10% → 50% → 100% for high-risk changes. 10% → 100% for low-risk changes. Never: 0% → 100% for anything that touches user-visible behavior.

Step 3: Choose a deployment strategy

Blue/green: spin up new environment, switch traffic, keep old environment warm for rollback
Canary: route a percentage of traffic to new version, measure, expand
Feature flags: deploy code dark, flip flag to enable for users
Rolling: replace instances one by one, abort if errors spike

Choose based on: how reversible is the change? How quickly can you detect problems?

Step 4: Define the deployment success criteria

Before deploying: what metrics must hold for the deployment to be considered successful?

Error rate stays below X%
p99 latency stays below Y ms
No new error types in logs
Key business metric (signups, orders) not regressing

Step 5: Bake time

After deploying to a stage: wait before expanding. Minimum bake time:

1% stage: 15 minutes
10% stage: 1 hour
50% stage: 4 hours

High-risk changes need longer bake times.

Step 6: Database migrations

Migrations must be backward compatible (old code + new schema must work)
Deploy migration before new code; keep old code running
Never delete a column in the same release that stops using it
Test rollback of the migration

Step 7: Automate the deployment gate

Success criteria from Step 4 must be checked automatically. If they fail, the deployment halts. Not: "someone watches the dashboard." Automatic.

Step 8: Post-deployment monitoring

After a deployment: watch the golden signals for 24 hours. Document any anomalies.

Anti-Rationalizations

"It's a small change — we can deploy to 100%" "Small" changes cause production incidents. All production changes go through staged rollout.

"We can roll back if there's a problem" "Can roll back" means the rollback procedure is written, tested, and can be executed in under 5 minutes. Otherwise, you don't have a rollback plan; you have a hope.

Verification Requirements

Rollback procedure written before deployment starts
Deployment stages defined (not 0% → 100%)
Success criteria defined and automated
Bake time defined at each stage
Database migrations are backward compatible
Post-deployment monitoring planned