fix(cli): add plan-gated property warnings to construct references

packages/cli/src/ai-context/references/configure-api-checks.md

@@ -7,6 +7,7 @@
 - If endpoints require authentication ask the user which authentication method to use and then generate a setupScript to authenticate the given requests.
 - Referenced `setup-script.ts` and `teardown-script.ts` for API checks must be plain ts files and not export anything.
 - Check in the code if API endpoints require authentication.
+- **Plan-gated properties:** `retryStrategy`, `runParallel`, and higher frequencies may not be available on all plans. Check entitlements matching `API_CHECKS_*` before using these. Omit any property whose entitlement is disabled. See `npx checkly skills manage` for details.
 
 <!-- EXAMPLE: API_CHECK -->
 

packages/cli/src/ai-context/references/configure-browser-checks.md

@@ -3,5 +3,6 @@
 - Import the `BrowserCheck` construct from `checkly/constructs`.
 - Generate a separate `.spec.ts` file for the Playwright code referenced in the `BrowserCheck` construct.
 - Use the `code.entrypoint` property to specify the path to your Playwright test file.
+- **Plan-gated properties:** `retryStrategy`, `runParallel`, and higher frequencies may not be available on all plans. Check entitlements matching `BROWSER_CHECKS_*` before using these. Omit any property whose entitlement is disabled. See `npx checkly skills manage` for details.
 
 <!-- EXAMPLE: BROWSER_CHECK -->

packages/cli/src/ai-context/references/configure-dns-monitors.md

@@ -3,5 +3,6 @@
 - Import the `DnsMonitor` construct from `checkly/constructs`.
 - Reference [the docs for DNS monitors](https://www.checklyhq.com/docs/constructs/dns-monitor/) before generating any code.
 - When adding `assertions`, always use `DnsAssertionBuilder` class.
+- **Plan-gated properties:** `retryStrategy`, `runParallel`, and higher frequencies are not available on all plans. Check entitlements matching `UPTIME_CHECKS_*` before using these. Omit any property whose entitlement is disabled. See `npx checkly skills manage` for details.
 
 <!-- EXAMPLE: DNS_MONITOR -->

packages/cli/src/ai-context/references/configure-icmp-monitors.md

@@ -5,5 +5,6 @@
 - When adding `assertions`, always use `IcmpAssertionBuilder` class.
 - Latency assertions require a property parameter: `'avg'`, `'min'`, `'max'`, or `'stdDev'`.
 - Use `degradedPacketLossThreshold` and `maxPacketLossThreshold` for packet loss thresholds (percentages).
+- **Plan-gated properties:** `retryStrategy`, `runParallel`, and higher frequencies are not available on all plans. Check entitlements matching `UPTIME_CHECKS_*` before using these. Omit any property whose entitlement is disabled. See `npx checkly skills manage` for details.
 
 <!-- EXAMPLE: ICMP_MONITOR -->

packages/cli/src/ai-context/references/configure-tcp-monitors.md

@@ -2,5 +2,6 @@
 
 - Import the `TcpMonitor` construct from `checkly/constructs`.
 - When adding `assertions`, always use `TcpAssertionBuilder` class for TCP monitors.
+- **Plan-gated properties:** `retryStrategy`, `runParallel`, and higher frequencies are not available on all plans. Check entitlements matching `UPTIME_CHECKS_*` before using these. Omit any property whose entitlement is disabled. See `npx checkly skills manage` for details.
 
 <!-- EXAMPLE: TCP_MONITOR -->

packages/cli/src/ai-context/references/configure-url-monitors.md

@@ -2,5 +2,6 @@
 
 - Import the `UrlMonitor` construct from `checkly/constructs`.
 - When adding `assertions`, always use `UrlAssertionBuilder`.
+- **Plan-gated properties:** `retryStrategy`, `runParallel`, and higher frequencies are not available on all plans. Check entitlements matching `UPTIME_CHECKS_*` before using these. Omit any property whose entitlement is disabled — Checkly applies safe defaults. See `npx checkly skills manage` for details.
 
 <!-- EXAMPLE: URL_MONITOR -->

packages/cli/src/ai-context/references/manage.md

@@ -19,6 +19,29 @@ This returns your entitlements (enabled/disabled with limits), available locatio
 - **Respect metered limits** (e.g. max browser checks, max alert channels)
 - **Surface upgrade paths** when a feature is disabled — each disabled entitlement includes an `upgradeUrl` pointing to the self-service checkout or the contact sales page
 
+## Applying entitlements to check configuration
+
+Entitlement keys follow the pattern `{CHECK_TYPE}_{FEATURE}` — match them to the check type you're configuring. Before setting any property on a check construct, find the corresponding entitlement and verify it's enabled.
+
+**Common plan-gated properties that agents get wrong on first setup:**
+
+| Check property | Entitlement pattern to search | What to do if disabled |
+|---|---|---|
+| `retryStrategy` | `*_RETRY_STRATEGY_*` and `*_MAX_RETRIES_*` for your check type | Omit `retryStrategy` entirely, or use only `NO_RETRY` |
+| `runParallel` | `*_SCHEDULING_STRATEGY_PARALLEL` for your check type | Omit `runParallel` or set to `false` (use round-robin) |
+| `frequency` | `*_FREQ_*` for your check type | Use only frequencies where the entitlement is enabled |
+| `locations` | `locations.all` array | Use only locations where `available` is `true` |
+| `privateLocation` | `PRIVATE_LOCATIONS` | Only available on Team plan and above |
+
+**How to check:** Use `--search` to narrow entitlements for the check type you're configuring:
+
+```bash
+npx checkly account plan --output json --search "uptime"
+npx checkly account plan --disabled --search "retry"
+```
+
+**When a feature is disabled:** Do not use it. Omit the property from the construct — Checkly will apply safe defaults. If the user needs the feature, share the `upgradeUrl` from the entitlement.
+
 ## Available Commands
 
 Parse and read further reference documentation for any of the following:

packages/cli/src/commands/account/plan.ts

@@ -108,19 +108,15 @@ export default class AccountPlan extends AuthCommand {
       )
     }
 
-    // JSON output (respects filters)
+    // JSON output (always includes plan context + locations)
     if (flags.output === 'json') {
       const enriched = filtered.map(e => withUpgradeUrl(e, checkoutUrl))
-      if (hasFilters) {
-        this.log(JSON.stringify(enriched, null, 2))
-      } else {
-        this.log(JSON.stringify({
-          ...plan,
-          checkoutUrl,
-          contactSalesUrl: CONTACT_SALES_URL,
-          entitlements: enriched,
-        }, null, 2))
-      }
+      this.log(JSON.stringify({
+        ...plan,
+        checkoutUrl,
+        contactSalesUrl: CONTACT_SALES_URL,
+        entitlements: enriched,
+      }, null, 2))
       return
     }