diff --git a/packages/aws-cdk/lib/api/deploy-stack.ts b/packages/aws-cdk/lib/api/deploy-stack.ts
index 6d3a5c71e79e9..b7b9fe7ce849b 100644
--- a/packages/aws-cdk/lib/api/deploy-stack.ts
+++ b/packages/aws-cdk/lib/api/deploy-stack.ts
@@ -7,7 +7,7 @@ import { prepareAssets } from '../assets';
 import { debug, error } from '../logging';
 import { Mode } from './aws-auth/credentials';
 import { ToolkitInfo } from './toolkit-info';
-import { describeStack, stackExists, waitForChangeSet, waitForStack } from './util/cloudformation';
+import { describeStack, stackExists, stackFailedCreating, waitForChangeSet, waitForStack } from './util/cloudformation';
 import { StackActivityMonitor } from './util/cloudformation/stack-activity-monitor';
 import { StackStatus } from './util/cloudformation/stack-status';
 import { SDK } from './util/sdk';
@@ -43,6 +43,15 @@ export async function deployStack(stack: cxapi.SynthesizedStack,
   const cfn = await sdk.cloudFormation(stack.environment, Mode.ForWriting);
   const bodyParameter = await makeBodyParameter(stack, toolkitInfo);
 
+  if (await stackFailedCreating(cfn, deployName)) {
+    debug(`Found existing stack ${deployName} that had previously failed creation. Deleting it before attempting to re-create it.`);
+    await cfn.deleteStack({ StackName: deployName }).promise();
+    const deletedStack = await waitForStack(cfn, deployName, false);
+    if (deletedStack && deletedStack.StackStatus !== 'DELETE_COMPLETE') {
+      throw new Error(`Failed deleting stack ${deployName} that had previously failed creation (current state: ${deletedStack.StackStatus})`);
+    }
+  }
+
   const update = await stackExists(cfn, deployName);
 
   const changeSetName = `CDK-${executionId}`;
diff --git a/packages/aws-cdk/lib/api/util/cloudformation.ts b/packages/aws-cdk/lib/api/util/cloudformation.ts
index 52f1bc076bfd1..3551bca8e7ae3 100644
--- a/packages/aws-cdk/lib/api/util/cloudformation.ts
+++ b/packages/aws-cdk/lib/api/util/cloudformation.ts
@@ -49,6 +49,20 @@ export async function stackExists(cfn: CloudFormation, stackName: string): Promi
   return description !== undefined;
 }
 
+/**
+ * Checks whether a stack has failed creation in CloudFormation. This is identified by the current stack Status being
+ * ``ROLLBACK_COMPLETE``.
+ *
+ * @param cfn       a CloudFormation client
+ * @param stackName the name of the stack to be checked for
+ *
+ * @returns +true+ if the stack exists and is in failed-creation state.
+ */
+export async function stackFailedCreating(cfn: CloudFormation, stackName: string): Promise<boolean> {
+  const description = await describeStack(cfn, stackName);
+  return description != null && description.StackStatus === 'ROLLBACK_COMPLETE';
+}
+
 /**
  * Waits for a function to return non-+undefined+ before returning.
  *