diff --git a/packages/cli/src/constructs/check-group.ts b/packages/cli/src/constructs/check-group.ts
index 70f0eca4..c4878493 100644
--- a/packages/cli/src/constructs/check-group.ts
+++ b/packages/cli/src/constructs/check-group.ts
@@ -282,7 +282,6 @@ export class CheckGroup extends Construct {
       name: this.name,
       activated: this.activated,
       muted: this.muted,
-      doubleCheck: this.doubleCheck,
       tags: this.tags,
       locations: this.locations,
       runtimeId: this.runtimeId,
@@ -295,7 +294,15 @@ export class CheckGroup extends Construct {
       localTearDownScript: this.localTearDownScript,
       apiCheckDefaults: this.apiCheckDefaults,
       environmentVariables: this.environmentVariables,
-      retryStrategy: this.retryStrategy,
+      // The backend doesn't actually support the `NO_RETRIES` type, it uses `null` instead.
+      retryStrategy: this.retryStrategy?.type === 'NO_RETRIES'
+        ? null
+        : this.retryStrategy,
+      // When `retryStrategy: NO_RETRIES` and `doubleCheck: undefined`, we want to let the user disable all retries.
+      // The backend has a Joi default of `doubleCheck: true`, though, so we need special handling for this case.
+      doubleCheck: this.doubleCheck === undefined && this.retryStrategy?.type === 'NO_RETRIES'
+        ? false
+        : this.doubleCheck,
       runParallel: this.runParallel,
       alertSettings: this.alertSettings,
       useGlobalAlertSettings: this.useGlobalAlertSettings,
diff --git a/packages/cli/src/constructs/check.ts b/packages/cli/src/constructs/check.ts
index ea055302..87472447 100644
--- a/packages/cli/src/constructs/check.ts
+++ b/packages/cli/src/constructs/check.ts
@@ -222,7 +222,6 @@ export abstract class Check extends Construct {
       name: this.name,
       activated: this.activated,
       muted: this.muted,
-      doubleCheck: this.doubleCheck,
       shouldFail: this.shouldFail,
       runtimeId: this.runtimeId,
       locations: this.locations,
@@ -235,7 +234,15 @@ export abstract class Check extends Construct {
       frequencyOffset: this.frequencyOffset,
       groupId: this.groupId,
       environmentVariables: this.environmentVariables,
-      retryStrategy: this.retryStrategy,
+      // The backend doesn't actually support the `NO_RETRIES` type, it uses `null` instead.
+      retryStrategy: this.retryStrategy?.type === 'NO_RETRIES'
+        ? null
+        : this.retryStrategy,
+      // When `retryStrategy: NO_RETRIES` and `doubleCheck: undefined`, we want to let the user disable all retries.
+      // The backend has a Joi default of `doubleCheck: true`, though, so we need special handling for this case.
+      doubleCheck: this.doubleCheck === undefined && this.retryStrategy?.type === 'NO_RETRIES'
+        ? false
+        : this.doubleCheck,
       alertSettings: this.alertSettings,
       useGlobalAlertSettings: this.useGlobalAlertSettings,
       runParallel: this.runParallel,
diff --git a/packages/cli/src/constructs/retry-strategy.ts b/packages/cli/src/constructs/retry-strategy.ts
index 731e29f2..9c5bddd1 100644
--- a/packages/cli/src/constructs/retry-strategy.ts
+++ b/packages/cli/src/constructs/retry-strategy.ts
@@ -1,4 +1,4 @@
-export type RetryStrategyType = 'LINEAR' | 'EXPONENTIAL' | 'FIXED'
+export type RetryStrategyType = 'LINEAR' | 'EXPONENTIAL' | 'FIXED' | 'NO_RETRIES'
 
 export interface RetryStrategy {
   type: RetryStrategyType,
@@ -55,6 +55,13 @@ export class RetryStrategyBuilder {
     return RetryStrategyBuilder.retryStrategy('EXPONENTIAL', options)
   }
 
+  /**
+   * No retries are performed.
+   */
+  static noRetries (): RetryStrategy {
+    return RetryStrategyBuilder.retryStrategy('NO_RETRIES')
+  }
+
   private static retryStrategy (type: RetryStrategyType, options?: RetryStrategyOptions): RetryStrategy {
     return {
       type,