Feature Flag Rollout Readiness Prompt

Identifies the specific flag being evaluated for rollout

checkout-v2-redesign

Must match an existing flag key in the feature management system. Validate against the flag registry or configuration store. Reject if null or empty.

Full flag configuration including targeting rules, percentage rollout, and variations

{"key":"checkout-v2","variations":["off","on"],"defaultRule":{"variation":"off"},"rules":[{"clauses":[{"attribute":"email","op":"endsWith","values":["@test.com"]}],"variation":"on"}]}

Must be valid JSON matching the flag provider schema. Parse and validate required fields: key, variations, defaultRule. Check that targeting rules reference real user attributes. Reject if schema validation fails.

Kill-switch or emergency-disable mechanism configuration for immediate flag deactivation

{"enabled":true,"trigger":"manual","fallbackVariation":"off","alertChannel":"#incidents"}

Must confirm kill-switch exists and is operational. Validate that fallbackVariation is a safe default. Check that alertChannel is a real notification target. Flag as blocking if kill-switch is absent or misconfigured.

List of services that depend on the flag state or are affected by the feature change

["api-gateway","checkout-service","payment-processor","inventory-sync"]

Must be a non-empty array of real service identifiers. Cross-reference against service catalog or deployment manifests. Validate that each service has defined owners and health endpoints. Flag any service without monitoring coverage.

Observability coverage: dashboards, alerts, and SLOs tracking the feature's behavior

{"dashboards":["checkout-latency","error-rates-v2"],"alerts":["checkout-error-spike","p99-latency-500ms"],"slo":"checkout-availability-99.9"}

Must include at least one dashboard, one alert, and one SLO reference. Validate that each dashboard and alert exists in the observability platform. Check that SLO has a defined error budget and burn rate alert. Flag missing coverage as a blocking finding.

Step-by-step rollback procedure if the flag causes issues after enablement

{"steps":[{"action":"disable-flag","target":"checkout-v2-redesign","verification":"checkout-error-rate-below-0.1%"},{"action":"clear-cache","target":"cdn-checkout-assets"}],"estimatedTimeSeconds":120,"owner":"checkout-team"}

Must contain at least one concrete rollback step with verification criteria. Validate that each step references real systems and that estimatedTimeSeconds is realistic. Check that owner is a real team or on-call rotation. Reject if rollback plan is empty or purely theoretical.

Broader release context: concurrent deployments, maintenance windows, and team availability

{"concurrentDeployments":["payment-service-v3"],"maintenanceWindow":"2025-01-15T02:00:00Z/2025-01-15T04:00:00Z","onCallRotation":"checkout-team-primary","stakeholders":["product-checkout","sre-platform"]}

Must include on-call rotation and stakeholder list. Validate that onCallRotation maps to a real escalation policy. Check that concurrentDeployments do not create circular dependencies. Flag if maintenance window is missing or team availability is unconfirmed.

string

Must match the [FLAG_ID] input exactly. Reject if missing or altered.

enum: ready | conditionally_ready | not_ready

Must be one of the three enum values. Reject any other string.

array of objects

Must be an array. If overall_readiness is ready, array must be empty. Each object must contain severity, category, and description fields.

enum: blocker | critical

Must be blocker or critical. Reject if any item uses a different severity label.

string

Must match one of the predefined categories: kill_switch, monitoring, dependency, rollback, config, observability. Reject unknown categories.

string

Must be non-empty and reference a specific finding, not a generic statement. Reject if length < 20 characters or contains only boilerplate.

array of objects

Must be an array. Each object must contain category and description fields. May be empty.

string

Must match one of the predefined categories. Reject unknown categories.

string

Must be non-empty and specific. Reject if identical to any blocking_items description.

object

Must contain covered_signals, missing_signals, and dashboard_url fields.

array of strings

Must list at least one signal. Reject if empty when overall_readiness is ready.

array of strings

Must be an array. If non-empty, overall_readiness must not be ready. Reject if missing_signals contains items also in covered_signals.

string or null

If provided, must match a valid URL pattern. Null allowed if no dashboard exists.

boolean

Must be true or false. Reject if null or string. If false and overall_readiness is ready, flag as eval failure.

object

Must contain steps array and estimated_recovery_time_minutes integer.

array of strings

Must contain at least one step. Each step must be a non-empty string describing a concrete action.

integer

Must be a positive integer. Reject if 0 or negative. Flag for human review if > 30.

array of strings

Must list all services that depend on this flag. May be empty. Reject if a listed service is not in the provided [DEPENDENCY_MAP].

number between 0.0 and 1.0

Must be a float between 0.0 and 1.0 inclusive. Reject if outside range. Flag if confidence > 0.9 but blocking_items is non-empty.

boolean

Must be true if blocking_items is non-empty or kill_switch_verified is false. Reject if false when blockers exist.

ISO 8601 timestamp

Must be a valid ISO 8601 string. Reject if unparseable or in the future beyond a 5-minute clock skew tolerance.

Prompt identifies all injected blocking conditions (missing kill-switch, no monitor, no rollback path) as BLOCKED

Output marks readiness as PROCEED when a known blocking condition exists in [FLAG_CONFIG]

Inject 3 golden configs with known blockers; assert output contains BLOCKED and lists each blocker by ID

Prompt flags any flag with fewer than 2 monitoring signals (error rate, latency, business metric) as INCOMPLETE

Output reports MONITORING_READY for a flag with zero dashboards or alerts configured

Provide [FLAG_CONFIG] with empty monitoring stanza; assert output includes OBSERVABILITY_GAP and recommends specific signals

Prompt verifies kill-switch exists, is tested within last 7 days, and has <5s propagation delay

Output accepts a kill-switch last tested 30 days ago or with no propagation SLA

Supply [FLAG_CONFIG] with stale kill-switch test date; assert output raises KILL_SWITCH_STALE with severity WARNING or BLOCKED

Prompt cross-references [DEPENDENCY_MAP] and flags any downstream service not yet deployed or verified

Output ignores a dependent service still in staging when primary service is marked ready

Provide [DEPENDENCY_MAP] with one service at version behind production; assert output lists DEPENDENCY_NOT_READY with service name and version gap

Prompt requires a documented rollback runbook with step count, estimated duration, and rollback trigger criteria

Output accepts ROLLBACK_READY when [ROLLBACK_RUNBOOK] is empty or contains only a placeholder

Supply empty or placeholder runbook; assert output includes ROLLBACK_PATH_INCOMPLETE and blocks proceed recommendation

Prompt produces a confidence score between 0.0 and 1.0 that drops below 0.5 when 2+ warnings exist

Confidence score remains above 0.7 despite multiple WARNING-level findings and one BLOCKED item

Run 10 varied [FLAG_CONFIG] inputs with known risk profiles; assert Spearman correlation >0.8 between risk count and confidence score

Prompt includes explicit human approval required for any BLOCKED item override or confidence <0.6

Output recommends PROCEED_WITH_OVERRIDE without marking HUMAN_APPROVAL_REQUIRED

Inject config with 1 BLOCKED item manually overridden; assert output contains HUMAN_APPROVAL_REQUIRED and lists the overridden item

Output matches [OUTPUT_SCHEMA] exactly: all required fields present, enums match allowed values, no extra fields

Output omits required field rollout_sequence or uses non-enum value for readiness_decision

Validate output against JSON Schema; assert no schema violations, all required fields non-null, enum values in allowed set