diff --git a/packages/aws-cdk/bin/cdk.ts b/packages/aws-cdk/bin/cdk.ts
index 8465f17af403f..aaaef0deb3182 100644
--- a/packages/aws-cdk/bin/cdk.ts
+++ b/packages/aws-cdk/bin/cdk.ts
@@ -105,7 +105,7 @@ async function parseCommandLineArguments() {
       .option('outputs-file', { type: 'string', alias: 'O', desc: 'Path to file where stack outputs will be written as JSON', requiresArg: true })
       .option('previous-parameters', { type: 'boolean', default: true, desc: 'Use previous values for existing parameters (you must specify all parameters on every deployment if this is disabled)' })
       .option('progress', { type: 'string', choices: [StackActivityProgress.BAR, StackActivityProgress.EVENTS], desc: 'Display mode for stack activity events' })
-      .option('rollback', { type: 'boolean', default: undefined, desc: 'Rollback stack to stable state on failure (iterate more rapidly with --no-rollback or -R)' })
+      .option('rollback', { type: 'boolean', desc: 'Rollback stack to stable state on failure (iterate more rapidly with --no-rollback or -R)' })
       // Hack to get '-R' as an alias for '--no-rollback', suggested by: https://github.com/yargs/yargs/issues/1729
       .option('R', { type: 'boolean', hidden: true })
       .middleware(yargsNegativeAlias('R', 'rollback'), true)
@@ -115,8 +115,7 @@ async function parseCommandLineArguments() {
           'which skips CloudFormation and updates the resources directly, ' +
           'and falls back to a full deployment if that is not possible. ' +
           'Do not use this in production environments',
-      })
-      .option('progress', { type: 'string', choices: [StackActivityProgress.BAR, StackActivityProgress.EVENTS], desc: 'Display mode for stack activity events' }),
+      }),
     )
     .command('destroy [STACKS..]', 'Destroy the stack(s) named STACKS', yargs => yargs
       .option('all', { type: 'boolean', default: false, desc: 'Destroy all available stacks' })
diff --git a/packages/aws-cdk/lib/api/deploy-stack.ts b/packages/aws-cdk/lib/api/deploy-stack.ts
index 3105d23fc00da..a40dc46194a4a 100644
--- a/packages/aws-cdk/lib/api/deploy-stack.ts
+++ b/packages/aws-cdk/lib/api/deploy-stack.ts
@@ -185,7 +185,7 @@ export interface DeployStackOptions {
    *
    * @default true
    */
-  readonly rollback?: boolean;
+  rollback?: boolean;
 
   /*
    * Whether to perform a 'hotswap' deployment.
@@ -250,6 +250,9 @@ export async function deployStack(options: DeployStackOptions): Promise<DeploySt
 
   await publishAssets(legacyAssets.toManifest(stackArtifact.assembly.directory), options.sdkProvider, stackEnv);
 
+  const shouldDisableRollback = (options.rollback === undefined && options.hotswap === true) || options.rollback === false;
+  options.rollback = shouldDisableRollback ? false : true;
+
   if (options.hotswap) {
     // attempt to short-circuit the deployment if possible
     const hotswapDeploymentResult = await tryHotswapDeployment(options.sdkProvider, assetParams, cloudFormationStack, stackArtifact);
@@ -326,14 +329,7 @@ async function prepareAndExecuteChangeSet(
 
     // Do a bit of contortions to only pass the `DisableRollback` flag if it's true. That way,
     // CloudFormation won't balk at the unrecognized option in regions where the feature is not available yet.
-    let disableRollback;
-
-    if (options.rollback === undefined && options.hotswap === true) {
-      disableRollback = { DisableRollback: true };
-    } else {
-      disableRollback = options.rollback === false ? { DisableRollback: true } : undefined;
-    }
-
+    const disableRollback = options.rollback === false ? { DisableRollback: true } : undefined;
     await cfn.executeChangeSet({ StackName: deployName, ChangeSetName: changeSetName, ...disableRollback }).promise();
 
     // eslint-disable-next-line max-len