Azure Deploy

Deploy workloads to Azure with a clear, low-risk process aligned with the Well-Architected Framework. Emphasis on idempotency, repeatable IaC, comprehensive validation, and reversible rollback paths.

Use This Skill When

• The user asks to deploy an app or service to Azure
• The user needs release automation, blue-green, or canary deployments
• The user wants Infrastructure-as-Code guidance (Bicep, Terraform)
• The user needs rollback and disaster recovery procedures
• Deployment fails and needs troubleshooting with validation steps

Context: Deployment Maturity Model

Stage 1: Manual → Portal-only, error-prone, hard to audit
Stage 2: Semi-Automated → Scripts with some IaC, inconsistent across environments
Stage 3: Fully Automated → Declarative IaC, CI/CD, infrastructure versioned ← Target
Stage 4: GitOps → All changes through pull requests, fully auditable, drift detection

Required Inputs

• Target environment: subscription ID, resource group, region, tenant
• Environment stage: dev, test, stage, prod (with distinct names)
• Workload type: web app, function, container app, AKS, VM, hybrid
• Deployment method: Azure CLI, Bicep, Terraform, ARM template, Azure Developer CLI
• Artifact readiness: built container image, versioned application package
• Security context: managed identity vs. connection string, private endpoints, secret rotation
• Validation criteria: health checks, endpoint tests, smoke tests, performance baselines
• Rollback tolerance: how many minutes can service be unavailable?

Decision Tree

Is this infrastructure or application code?
├─ Infrastructure → Use Bicep or Terraform (IaC)
└─ Application → Use Azure DevOps or GitHub Actions pipeline

Is this a net-new deployment or an update?
├─ Net-new → Deploy with full validation suite
└─ Update → Blue-green or canary strategy to minimize blast radius

Do you need instant rollback capability?
├─ Yes → Blue-green deployment (dual environments, instant traffic switch)
└─ Acceptable lag → Canary (gradual rollout with monitoring)

Workflow

Phase 1: Pre-Deployment Validation (Shift-left)

1. Verify prerequisites:

   • Subscription access confirmed (check quota, resource limits, API provider registration)
   • Role assignments correct for service principals or managed identities
   • Naming conventions followed (avoid reserved names, region abbreviations)
   • All secrets exist in Key Vault or secure store (never hardcode)

2. Review IaC and artifacts:

   • Bicep/Terraform syntax validated with bicep build or terraform plan
   • No hardcoded values (use parameters and variables)
   • Dependencies explicitly declared (dependsOn, references)
   • Tags and metadata complete (owner, environment, cost center)

3. Validate security posture:

   • Network isolation: private endpoints, NSGs, firewalls
   • Identity: managed identity or service principal with least privilege
   • Data: encryption at rest and in transit
   • Secrets stored in Key Vault with access policy

Phase 2: Artifact Preparation

1. Build application:

   • Compile, test, and package application code
   • Increment version number (semantic versioning)
   • Tag artifacts with build ID or commit hash for traceability

2. Build container (if containerized):

   • Push to Azure Container Registry (ACR) with multi-tag (:latest, :v1.2.3, :sha-abcd1234)
   • Scan image for vulnerabilities using Defender for container registries
   • Verify image can be pulled from target deployment context

3. Archive IaC:

   • Version Bicep or Terraform files in source control
   • Pin module versions (never use latest)
   • Generate parameter files for each environment (dev.bicepparam, prod.bicepparam)

Phase 3: Deployment Execution

Option A: Declarative (Recommended)

az deployment group create \
  --resource-group $RG \
  --template-file main.bicep \
  --parameters main.bicepparam \
  --mode Incremental

Option B: Terraform

terraform init -backend-config=backend.tfvars
terraform plan -var-file=prod.tfvars -out=tfplan
terraform apply tfplan

4. Monitor deployment progress:
   • Watch Azure portal Activity Log or CLI output for errors
   • Check resource creation order (dependencies respected)
   • Verify DNS, network routes, and storage connectivity as resources come online

Phase 4: Post-Deployment Validation

1. Smoke test:

   • Application endpoint responds (HTTP 200, health check passes)
   • Database or data store is accessible
   • Logging and monitoring are active

2. Integration test:

   • Dependent services (API gateways, queues, caches) are reachable
   • Data flows through expected paths
   • Performance is within SLA targets

3. Security validation:

   • Public exposure is blocked (no public IPs unless required)
   • Managed identity credentials are working
   • Key Vault access is functional

4. Compliance check:

   • Tags and ownership metadata present
   • Resource names follow naming convention
   • Diagnostic logging configured

Phase 5: Rollback & Recovery

Immediate Rollback (Minutes):

• Blue-green: Switch traffic back to old deployment (instant)
• Container/App Service: Revert to previous deployment slot or image version

Longer Rollback (Hours):

• Re-deploy previous IaC snapshot from version control
• Point application to previous database snapshot
• Update DNS or traffic manager to old infrastructure

Full Disaster Recovery:

• Restore from backup or failover to secondary region
• Validate data consistency and application state
• Perform security re-validation before resuming production traffic

Output Contract

Return these sections in order:

1. Deployment Plan Summary

   • Environment, resource group, region
   • Estimated lead time for quota increases (if needed)
   • High-level resource inventory and costs

2. Pre-Deployment Checklist

   • Prerequisites validation commands or portal steps
   • Required role assignments and permissions
   • Security and networking decisions

3. Deployment Commands or IaC

   • Exact CLI/Terraform/Bicep commands with parameter values
   • Suggested order of operations
   • Parallel vs. sequential resource creation notes

4. Post-Deployment Validation Checklist

   • Smoke test steps (curl commands, portal checks)
   • Integration test scenarios
   • Performance baseline commands (ab, loadtest, etc.)

5. Rollback Procedure

   • Step-by-step rollback sequence
   • How long rollback takes
   • Data consistency checks post-rollback

6. Risks and Assumptions

   • Quota headroom assumptions
   • Blast radius if deployment fails mid-stream
   • Dependencies on external systems

Practical Examples

Example 1: Deploy a Container App with Traffic Split (Canary)

1. Deploy new revision to staging slot: 5% traffic
2. Monitor error rate and latency for 10 minutes
3. Shift to 25%, then 50%, then 100% in 10-minute intervals
4. If error spike detected, instant rollback to previous revision

Example 2: Blue-Green Web App Deployment

1. Deploy new version to unused deployment slot (green)
2. Run smoke and integration tests against green slot
3. Swap slots: green becomes production (instant, no downtime)
4. Keep blue slot warm for quick rollback within 1 hour

Example 3: Bicep Deployment with Parameter Overrides

az deployment group create \
  --resource-group myapp-prod \
  --template-file main.bicep \
  --parameters main.bicepparam \
  --parameters location=eastus vmCount=3 \
  --mode Incremental

Guardrails

• Never hardcode secrets or connection strings in IaC, templates, or environment variables. Use Key Vault with managed identity.
• Always use --mode Incremental for Bicep/ARM; avoid Complete mode unless you intend to delete unlisted resources.
• Avoid manual post-deployment configuration (portal UI changes). All config must be in IaC for reproducibility.
• Call out destructive operations (database migrations, resource deletions, scale-down) before execution.
• Version everything: application code, container images, IaC modules, parameter files.
• Never use latest image tag in production; pin to specific versions.
• Test rollback procedure before going to production; don't assume it works untested.
• Separate credentials by environment; dev/test/prod each have distinct service principals and Key Vault instances.