diff --git a/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/bootstrap/cdk-bootstrap-can-re-bootstrap-after-stack-deletion.integtest.ts b/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/bootstrap/cdk-bootstrap-can-re-bootstrap-after-stack-deletion.integtest.ts
new file mode 100644
index 000000000..23320d345
--- /dev/null
+++ b/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/bootstrap/cdk-bootstrap-can-re-bootstrap-after-stack-deletion.integtest.ts
@@ -0,0 +1,21 @@
+import { integTest, withoutBootstrap } from '../../../lib';
+
+integTest('bootstrap can re-bootstrap after stack deletion', withoutBootstrap(async (fixture) => {
+  const bootstrapStackName = fixture.bootstrapStackName;
+
+  // Bootstrap the environment
+  await fixture.cdkBootstrapModern({
+    toolkitStackName: bootstrapStackName,
+    cfnExecutionPolicy: 'arn:aws:iam::aws:policy/AdministratorAccess',
+  });
+
+  // Delete the bootstrap stack (resources like the S3 bucket will be retained)
+  await fixture.aws.deleteStacks(bootstrapStackName);
+
+  // Re-bootstrap should succeed because importExistingResources is enabled,
+  // allowing the change set to import the retained resources back into the stack.
+  await fixture.cdkBootstrapModern({
+    toolkitStackName: bootstrapStackName,
+    cfnExecutionPolicy: 'arn:aws:iam::aws:policy/AdministratorAccess',
+  });
+}));
diff --git a/packages/@aws-cdk/toolkit-lib/lib/api/bootstrap/bootstrap-props.ts b/packages/@aws-cdk/toolkit-lib/lib/api/bootstrap/bootstrap-props.ts
index 8f0225126..ad525baa3 100644
--- a/packages/@aws-cdk/toolkit-lib/lib/api/bootstrap/bootstrap-props.ts
+++ b/packages/@aws-cdk/toolkit-lib/lib/api/bootstrap/bootstrap-props.ts
@@ -58,6 +58,14 @@ export interface BootstrapEnvironmentOptions {
    * @default true
    */
   usePreviousParameters?: boolean;
+
+  /**
+   * Whether to import existing resources into the stack instead of failing
+   * when they already exist.
+   *
+   * @default true
+   */
+  readonly importExistingResources?: boolean;
 }
 
 /**
diff --git a/packages/@aws-cdk/toolkit-lib/lib/api/bootstrap/deploy-bootstrap.ts b/packages/@aws-cdk/toolkit-lib/lib/api/bootstrap/deploy-bootstrap.ts
index 4ab2dab56..89e88fc55 100644
--- a/packages/@aws-cdk/toolkit-lib/lib/api/bootstrap/deploy-bootstrap.ts
+++ b/packages/@aws-cdk/toolkit-lib/lib/api/bootstrap/deploy-bootstrap.ts
@@ -142,7 +142,11 @@ export class BootstrapStack {
         forceDeployment: options.forceDeployment,
         roleArn: options.roleArn,
         tags: options.tags,
-        deploymentMethod: { method: 'change-set', execute: options.execute },
+        deploymentMethod: {
+          method: 'change-set',
+          execute: options.execute,
+          importExistingResources: options.importExistingResources ?? true,
+        },
         parameters,
         usePreviousParameters: options.usePreviousParameters ?? true,
         // Obviously we can't need a bootstrap stack to deploy a bootstrap stack
diff --git a/packages/aws-cdk/lib/cli/cli-config.ts b/packages/aws-cdk/lib/cli/cli-config.ts
index 9c39a5083..ffb8f0119 100644
--- a/packages/aws-cdk/lib/cli/cli-config.ts
+++ b/packages/aws-cdk/lib/cli/cli-config.ts
@@ -102,6 +102,7 @@ export async function makeConfig(): Promise<CliConfig> {
           'toolkit-stack-name': { type: 'string', desc: 'The name of the CDK toolkit stack to create', requiresArg: true },
           'template': { type: 'string', requiresArg: true, desc: 'Use the template from the given file instead of the built-in one (use --show-template to obtain an example)' },
           '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)' },
+          'import-existing-resources': { type: 'boolean', desc: 'Whether to import existing resources into the bootstrap stack instead of failing if they already exist', default: true },
         },
       },
       'gc': {
diff --git a/packages/aws-cdk/lib/cli/cli-type-registry.json b/packages/aws-cdk/lib/cli/cli-type-registry.json
index fbab3f012..97aeea0b5 100644
--- a/packages/aws-cdk/lib/cli/cli-type-registry.json
+++ b/packages/aws-cdk/lib/cli/cli-type-registry.json
@@ -306,6 +306,11 @@
           "type": "boolean",
           "default": true,
           "desc": "Use previous values for existing parameters (you must specify all parameters on every deployment if this is disabled)"
+        },
+        "import-existing-resources": {
+          "type": "boolean",
+          "desc": "Whether to import existing resources into the bootstrap stack instead of failing if they already exist",
+          "default": true
         }
       }
     },
diff --git a/packages/aws-cdk/lib/cli/cli.ts b/packages/aws-cdk/lib/cli/cli.ts
index 173b2e193..f406498e0 100644
--- a/packages/aws-cdk/lib/cli/cli.ts
+++ b/packages/aws-cdk/lib/cli/cli.ts
@@ -385,6 +385,7 @@ export async function exec(args: string[], synthesizer?: Synthesizer): Promise<n
           tags: configuration.settings.get(['tags']),
           terminationProtection: args.terminationProtection,
           usePreviousParameters: args['previous-parameters'],
+          importExistingResources: args.importExistingResources,
           parameters: {
             bucketName: configuration.settings.get(['toolkitBucket', 'bucketName']),
             kmsKeyId: configuration.settings.get(['toolkitBucket', 'kmsKeyId']),
diff --git a/packages/aws-cdk/lib/cli/convert-to-user-input.ts b/packages/aws-cdk/lib/cli/convert-to-user-input.ts
index a1d8cfc70..0814c0b1d 100644
--- a/packages/aws-cdk/lib/cli/convert-to-user-input.ts
+++ b/packages/aws-cdk/lib/cli/convert-to-user-input.ts
@@ -82,6 +82,7 @@ export function convertYargsToUserInput(args: any): UserInput {
         toolkitStackName: args.toolkitStackName,
         template: args.template,
         previousParameters: args.previousParameters,
+        importExistingResources: args.importExistingResources,
         ENVIRONMENTS: args.ENVIRONMENTS,
       };
       break;
@@ -412,6 +413,7 @@ export function convertConfigToUserInput(config: any): UserInput {
     toolkitStackName: config.bootstrap?.toolkitStackName,
     template: config.bootstrap?.template,
     previousParameters: config.bootstrap?.previousParameters,
+    importExistingResources: config.bootstrap?.importExistingResources,
   };
   const gcOptions = {
     action: config.gc?.action,
diff --git a/packages/aws-cdk/lib/cli/parse-command-line-arguments.ts b/packages/aws-cdk/lib/cli/parse-command-line-arguments.ts
index 876ac8403..56700278b 100644
--- a/packages/aws-cdk/lib/cli/parse-command-line-arguments.ts
+++ b/packages/aws-cdk/lib/cli/parse-command-line-arguments.ts
@@ -335,6 +335,11 @@ export function parseCommandLineArguments(args: Array<string>): any {
           default: true,
           type: 'boolean',
           desc: 'Use previous values for existing parameters (you must specify all parameters on every deployment if this is disabled)',
+        })
+        .option('import-existing-resources', {
+          default: true,
+          type: 'boolean',
+          desc: 'Whether to import existing resources into the bootstrap stack instead of failing if they already exist',
         }),
     )
     .command(
diff --git a/packages/aws-cdk/lib/cli/user-input.ts b/packages/aws-cdk/lib/cli/user-input.ts
index afb41f997..08d103b42 100644
--- a/packages/aws-cdk/lib/cli/user-input.ts
+++ b/packages/aws-cdk/lib/cli/user-input.ts
@@ -592,6 +592,13 @@ export interface BootstrapOptions {
    */
   readonly previousParameters?: boolean;
 
+  /**
+   * Whether to import existing resources into the bootstrap stack instead of failing if they already exist
+   *
+   * @default - true
+   */
+  readonly importExistingResources?: boolean;
+
   /**
    * Positional argument for bootstrap
    */