diff --git a/packages/@aws-cdk-testing/cli-integ/lib/eventually.ts b/packages/@aws-cdk-testing/cli-integ/lib/eventually.ts
new file mode 100644
index 0000000000000..6936ff32f76fd
--- /dev/null
+++ b/packages/@aws-cdk-testing/cli-integ/lib/eventually.ts
@@ -0,0 +1,42 @@
+/**
+ * @param maxAttempts the maximum number of attempts
+ * @param interval interval in milliseconds to observe between attempts
+ */
+export type EventuallyOptions = {
+  maxAttempts?: number;
+  interval?: number;
+};
+
+const wait = (ms: number): Promise<void> => new Promise((resolve) => setTimeout(resolve, ms));
+const DEFAULT_INTERVAL = 1000;
+const DEFAULT_MAX_ATTEMPTS = 10;
+
+/**
+ * Runs a function on an interval until the maximum number of attempts has
+ * been reached.
+ *
+ * Default interval = 1000 milliseconds
+ * Default maxAttempts = 10
+ *
+ * @param fn function to run
+ * @param options EventuallyOptions
+ */
+const eventually = async <T>(call: () => Promise<T>, options?: EventuallyOptions): Promise<T> => {
+  const opts = {
+    interval: options?.interval ? options.interval : DEFAULT_INTERVAL,
+    maxAttempts: options?.maxAttempts ? options.maxAttempts : DEFAULT_MAX_ATTEMPTS,
+  };
+
+  while (opts.maxAttempts-- >= 0) {
+    try {
+      return await call();
+    } catch (err) {
+      if (opts.maxAttempts <= 0) throw err;
+    }
+    await wait(opts.interval);
+  }
+
+  throw new Error('An unexpected error has occurred.');
+};
+
+export default eventually;
\ No newline at end of file
diff --git a/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/bootstrapping.integtest.ts b/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/bootstrapping.integtest.ts
index 18889bde7dd7e..ab56611bf39e0 100644
--- a/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/bootstrapping.integtest.ts
+++ b/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/bootstrapping.integtest.ts
@@ -3,6 +3,7 @@ import * as fs from 'fs';
 import * as path from 'path';
 import * as yaml from 'yaml';
 import { integTest, randomString, withoutBootstrap } from '../../lib';
+import eventually from '../../lib/eventually';
 
 jest.setTimeout(2 * 60 * 60_000); // Includes the time to acquire locks, worst-case single-threaded runtime
 
@@ -283,17 +284,25 @@ integTest('can remove customPermissionsBoundary', withoutBootstrap(async (fixtur
       }),
     });
     policyArn = policy.Policy?.Arn;
-    await fixture.cdkBootstrapModern({
-      // toolkitStackName doesn't matter for this particular invocation
-      toolkitStackName: bootstrapStackName,
-      customPermissionsBoundary: policyName,
-    });
 
-    const response = await fixture.aws.cloudFormation('describeStacks', { StackName: bootstrapStackName });
-    expect(
-      response.Stacks?.[0].Parameters?.some(
-        param => (param.ParameterKey === 'InputPermissionsBoundary' && param.ParameterValue === policyName),
-      )).toEqual(true);
+    // Policy creation and consistency across regions is "almost immediate"
+    // See: https://docs.aws.amazon.com/IAM/latest/UserGuide/troubleshoot_general.html#troubleshoot_general_eventual-consistency
+    // We will put this in an `eventually` block to retry stack creation with a reasonable timeout
+    const createStackWithPermissionBoundary = async (): Promise<void> => {
+      await fixture.cdkBootstrapModern({
+        // toolkitStackName doesn't matter for this particular invocation
+        toolkitStackName: bootstrapStackName,
+        customPermissionsBoundary: policyName,
+      });
+
+      const response = await fixture.aws.cloudFormation('describeStacks', { StackName: bootstrapStackName });
+      expect(
+        response.Stacks?.[0].Parameters?.some(
+          param => (param.ParameterKey === 'InputPermissionsBoundary' && param.ParameterValue === policyName),
+        )).toEqual(true);
+    };
+
+    await eventually(createStackWithPermissionBoundary, { maxAttempts: 3 });
 
     await fixture.cdkBootstrapModern({
       // toolkitStackName doesn't matter for this particular invocation