diff --git a/packages/@aws-cdk/aws-codedeploy/lib/utils.ts b/packages/@aws-cdk/aws-codedeploy/lib/utils.ts
index 6c5381b0de96b..834e5afb506e9 100644
--- a/packages/@aws-cdk/aws-codedeploy/lib/utils.ts
+++ b/packages/@aws-cdk/aws-codedeploy/lib/utils.ts
@@ -58,6 +58,14 @@ CfnDeploymentGroup.AutoRollbackConfigurationProperty | undefined {
     }
   }
 
+  if (autoRollbackConfig.failedDeployment === false
+    && autoRollbackConfig.stoppedDeployment !== true
+    && autoRollbackConfig.deploymentInAlarm === false) {
+    return {
+      enabled: false,
+    };
+  }
+
   return events.length > 0
     ? {
       enabled: true,
diff --git a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/aws-cdk-codedeploy-server-dg.assets.json b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/aws-cdk-codedeploy-server-dg.assets.json
index 2798a5e21b7ed..e8cf7cae4d1a1 100644
--- a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/aws-cdk-codedeploy-server-dg.assets.json
+++ b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/aws-cdk-codedeploy-server-dg.assets.json
@@ -1,7 +1,7 @@
 {
-  "version": "20.0.0",
+  "version": "21.0.0",
   "files": {
-    "dae40555b89ef1d396d170d34f146291ebc161a078ebd48290cc01135f3291da": {
+    "5088f12eca5c246f5575ce7f87af7fe359933f451dfd57b1c97881139e63533b": {
       "source": {
         "path": "aws-cdk-codedeploy-server-dg.template.json",
         "packaging": "file"
@@ -9,7 +9,7 @@
       "destinations": {
         "current_account-current_region": {
           "bucketName": "cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}",
-          "objectKey": "dae40555b89ef1d396d170d34f146291ebc161a078ebd48290cc01135f3291da.json",
+          "objectKey": "5088f12eca5c246f5575ce7f87af7fe359933f451dfd57b1c97881139e63533b.json",
           "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-file-publishing-role-${AWS::AccountId}-${AWS::Region}"
         }
       }
diff --git a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/aws-cdk-codedeploy-server-dg.template.json b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/aws-cdk-codedeploy-server-dg.template.json
index c88eb3bf11754..7b5a855c7b85c 100644
--- a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/aws-cdk-codedeploy-server-dg.template.json
+++ b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/aws-cdk-codedeploy-server-dg.template.json
@@ -722,6 +722,9 @@
      ],
      "Enabled": true
     },
+    "AutoRollbackConfiguration": {
+     "Enabled": false
+    },
     "AutoScalingGroups": [
      {
       "Ref": "ASG46ED3070"
diff --git a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/cdk.out b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/cdk.out
index 588d7b269d34f..8ecc185e9dbee 100644
--- a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/cdk.out
+++ b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/cdk.out
@@ -1 +1 @@
-{"version":"20.0.0"}
\ No newline at end of file
+{"version":"21.0.0"}
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/integ.json b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/integ.json
index 58f83ae205d9e..526dd5e6267fd 100644
--- a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/integ.json
+++ b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/integ.json
@@ -1,5 +1,5 @@
 {
-  "version": "20.0.0",
+  "version": "21.0.0",
   "testCases": {
     "integ.deployment-group": {
       "stacks": [
diff --git a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/manifest.json b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/manifest.json
index 76cea921604a5..13d311b7d7966 100644
--- a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/manifest.json
+++ b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/manifest.json
@@ -1,5 +1,5 @@
 {
-  "version": "20.0.0",
+  "version": "21.0.0",
   "artifacts": {
     "Tree": {
       "type": "cdk:tree",
@@ -23,7 +23,7 @@
         "validateOnSynth": false,
         "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-deploy-role-${AWS::AccountId}-${AWS::Region}",
         "cloudFormationExecutionRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-cfn-exec-role-${AWS::AccountId}-${AWS::Region}",
-        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/dae40555b89ef1d396d170d34f146291ebc161a078ebd48290cc01135f3291da.json",
+        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/5088f12eca5c246f5575ce7f87af7fe359933f451dfd57b1c97881139e63533b.json",
         "requiresBootstrapStackVersion": 6,
         "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version",
         "additionalDependencies": [
diff --git a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/tree.json b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/tree.json
index cf2da82803f45..ba0b61498e104 100644
--- a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/tree.json
+++ b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.integ.snapshot/tree.json
@@ -9,7 +9,7 @@
         "path": "Tree",
         "constructInfo": {
           "fqn": "constructs.Construct",
-          "version": "10.1.85"
+          "version": "10.1.102"
         }
       },
       "aws-cdk-codedeploy-server-dg": {
@@ -91,8 +91,8 @@
                     "id": "Acl",
                     "path": "aws-cdk-codedeploy-server-dg/VPC/PublicSubnet1/Acl",
                     "constructInfo": {
-                      "fqn": "constructs.Construct",
-                      "version": "10.1.85"
+                      "fqn": "@aws-cdk/core.Resource",
+                      "version": "0.0.0"
                     }
                   },
                   "RouteTable": {
@@ -258,8 +258,8 @@
                     "id": "Acl",
                     "path": "aws-cdk-codedeploy-server-dg/VPC/PublicSubnet2/Acl",
                     "constructInfo": {
-                      "fqn": "constructs.Construct",
-                      "version": "10.1.85"
+                      "fqn": "@aws-cdk/core.Resource",
+                      "version": "0.0.0"
                     }
                   },
                   "RouteTable": {
@@ -425,8 +425,8 @@
                     "id": "Acl",
                     "path": "aws-cdk-codedeploy-server-dg/VPC/PrivateSubnet1/Acl",
                     "constructInfo": {
-                      "fqn": "constructs.Construct",
-                      "version": "10.1.85"
+                      "fqn": "@aws-cdk/core.Resource",
+                      "version": "0.0.0"
                     }
                   },
                   "RouteTable": {
@@ -544,8 +544,8 @@
                     "id": "Acl",
                     "path": "aws-cdk-codedeploy-server-dg/VPC/PrivateSubnet2/Acl",
                     "constructInfo": {
-                      "fqn": "constructs.Construct",
-                      "version": "10.1.85"
+                      "fqn": "@aws-cdk/core.Resource",
+                      "version": "0.0.0"
                     }
                   },
                   "RouteTable": {
@@ -936,16 +936,16 @@
             "id": "SsmParameterValue:--aws--service--ami-amazon-linux-latest--amzn-ami-hvm-x86_64-gp2:C96584B6-F00A-464E-AD19-53AFF4B05118.Parameter",
             "path": "aws-cdk-codedeploy-server-dg/SsmParameterValue:--aws--service--ami-amazon-linux-latest--amzn-ami-hvm-x86_64-gp2:C96584B6-F00A-464E-AD19-53AFF4B05118.Parameter",
             "constructInfo": {
-              "fqn": "constructs.Construct",
-              "version": "10.1.85"
+              "fqn": "@aws-cdk/core.CfnParameter",
+              "version": "0.0.0"
             }
           },
           "SsmParameterValue:--aws--service--ami-amazon-linux-latest--amzn-ami-hvm-x86_64-gp2:C96584B6-F00A-464E-AD19-53AFF4B05118": {
             "id": "SsmParameterValue:--aws--service--ami-amazon-linux-latest--amzn-ami-hvm-x86_64-gp2:C96584B6-F00A-464E-AD19-53AFF4B05118",
             "path": "aws-cdk-codedeploy-server-dg/SsmParameterValue:--aws--service--ami-amazon-linux-latest--amzn-ami-hvm-x86_64-gp2:C96584B6-F00A-464E-AD19-53AFF4B05118",
             "constructInfo": {
-              "fqn": "constructs.Construct",
-              "version": "10.1.85"
+              "fqn": "@aws-cdk/core.Resource",
+              "version": "0.0.0"
             }
           },
           "ELB": {
@@ -1190,6 +1190,9 @@
                       ],
                       "enabled": true
                     },
+                    "autoRollbackConfiguration": {
+                      "enabled": false
+                    },
                     "autoScalingGroups": [
                       {
                         "Ref": "ASG46ED3070"
@@ -1225,20 +1228,20 @@
             "id": "Service-principalMap",
             "path": "aws-cdk-codedeploy-server-dg/Service-principalMap",
             "constructInfo": {
-              "fqn": "constructs.Construct",
-              "version": "10.1.85"
+              "fqn": "@aws-cdk/core.CfnMapping",
+              "version": "0.0.0"
             }
           }
         },
         "constructInfo": {
-          "fqn": "constructs.Construct",
-          "version": "10.1.85"
+          "fqn": "@aws-cdk/core.Stack",
+          "version": "0.0.0"
         }
       }
     },
     "constructInfo": {
-      "fqn": "constructs.Construct",
-      "version": "10.1.85"
+      "fqn": "@aws-cdk/core.App",
+      "version": "0.0.0"
     }
   }
 }
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.test.ts b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.test.ts
index c01a8ae8ef34d..6b22a90cbeedb 100644
--- a/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.test.ts
+++ b/packages/@aws-cdk/aws-codedeploy/test/server/deployment-group.test.ts
@@ -412,6 +412,42 @@ describe('CodeDeploy Server Deployment Group', () => {
     expect(() => app.synth()).toThrow(/deploymentInAlarm/);
   });
 
+  test('disable automatic rollback', () => {
+    const stack = new cdk.Stack();
+
+    new codedeploy.ServerDeploymentGroup(stack, 'DeploymentGroup', {
+      autoRollback: {
+        deploymentInAlarm: false,
+        failedDeployment: false,
+      },
+    });
+
+    Template.fromStack(stack).hasResourceProperties('AWS::CodeDeploy::DeploymentGroup', {
+      'AutoRollbackConfiguration': {
+        'Enabled': false,
+      },
+    });
+  });
+
+  test('disable automatic rollback when all options are false', () => {
+    const stack = new cdk.Stack();
+
+    new codedeploy.ServerDeploymentGroup(stack, 'DeploymentGroup', {
+      autoRollback: {
+        deploymentInAlarm: false,
+        failedDeployment: false,
+        stoppedDeployment: false,
+      },
+    });
+
+    Template.fromStack(stack).hasResourceProperties('AWS::CodeDeploy::DeploymentGroup', {
+      'AutoRollbackConfiguration': {
+        'Enabled': false,
+      },
+    });
+  });
+
+
   test('can be used with an imported ALB Target Group as the load balancer', () => {
     const stack = new cdk.Stack();