diff --git a/packages/aws-cdk-lib/aws-ec2/lib/ip-addresses.ts b/packages/aws-cdk-lib/aws-ec2/lib/ip-addresses.ts
index d6b4e7cb0b93d..6d0085fe312f1 100644
--- a/packages/aws-cdk-lib/aws-ec2/lib/ip-addresses.ts
+++ b/packages/aws-cdk-lib/aws-ec2/lib/ip-addresses.ts
@@ -1,4 +1,4 @@
-import { calculateCidrSplits } from './cidr-splits';
+import { CidrSplit, calculateCidrSplits } from './cidr-splits';
 import { NetworkBuilder } from './network-util';
 import { SubnetConfiguration } from './vpc';
 import { Fn, Token } from '../../core';
@@ -230,7 +230,7 @@ class AwsIpam implements IIpAddresses {
 
     const allocatedSubnets: AllocatedSubnet[] = cidrSplit.map(subnet => {
       return {
-        cidr: Fn.select(subnet.index, Fn.cidr(input.vpcCidr, subnet.count, `${32-subnet.netmask}`)),
+        cidr: cidrSplitToCfnExpression(input.vpcCidr, subnet),
       };
     });
 
@@ -241,6 +241,45 @@ class AwsIpam implements IIpAddresses {
   }
 }
 
+/**
+ * Convert a CIDR split command to a CFN expression that calculates the same CIDR
+ *
+ * Can recursively produce multiple `{ Fn::Cidr }` expressions.
+ *
+ * This is necessary because CFN's `{ Fn::Cidr }` reifies the split to an actual list of
+ * strings, and to limit resource consumption `count` may never be higher than 256. So
+ * if we need to split deeper, we need to do more than one split.
+ *
+ * (Function public for testing)
+ */
+export function cidrSplitToCfnExpression(parentCidr: string, split: CidrSplit) {
+  const MAX_COUNT = 256;
+  const MAX_COUNT_BITS = 8;
+
+  if (split.count === 1) {
+    return parentCidr;
+  }
+
+  if (split.count <= MAX_COUNT) {
+    return Fn.select(split.index, Fn.cidr(parentCidr, split.count, `${32-split.netmask}`));
+  }
+
+  if (split.netmask - MAX_COUNT_BITS < 1) {
+    throw new Error(`Cannot split an IP range into ${split.count} /${split.netmask}s`);
+  }
+
+  const parentSplit = {
+    netmask: split.netmask - MAX_COUNT_BITS,
+    count: Math.ceil(split.count / MAX_COUNT),
+    index: Math.floor(split.index / MAX_COUNT),
+  };
+  return cidrSplitToCfnExpression(cidrSplitToCfnExpression(parentCidr, parentSplit), {
+    netmask: split.netmask,
+    count: MAX_COUNT,
+    index: split.index - (parentSplit.index * MAX_COUNT),
+  });
+}
+
 /**
  * Implements static Ip assignment locally.
  *
diff --git a/packages/aws-cdk-lib/aws-ec2/test/ip-addresses.test.ts b/packages/aws-cdk-lib/aws-ec2/test/ip-addresses.test.ts
index e443f5fddd670..e766c475e5dcb 100644
--- a/packages/aws-cdk-lib/aws-ec2/test/ip-addresses.test.ts
+++ b/packages/aws-cdk-lib/aws-ec2/test/ip-addresses.test.ts
@@ -1,7 +1,8 @@
 
 import { Template } from '../../assertions';
 import { Stack } from '../../core';
-import { IpAddresses, SubnetType, Vpc } from '../lib';
+import { IpAddresses, SubnetType, Vpc, cidrSplitToCfnExpression } from '../lib';
+import { CidrSplit } from '../lib/cidr-splits';
 
 describe('Cidr vpc allocation', () => {
 
@@ -406,5 +407,35 @@ describe('AwsIpam Vpc Integration', () => {
     template.resourceCountIs('AWS::EC2::Subnet', 2);
 
   });
-
 });
+
+type CfnSplit = {
+  count: number;
+  hostbits: number;
+  select: number;
+}
+
+test.each([
+  // Index into first block
+  [{ count: 4096, netmask: 28, index: 123 }, /* -> */ { count: 16, hostbits: 12, select: 0 }, { count: 256, hostbits: 4, select: 123 }],
+  // Index into second block
+  [{ count: 4096, netmask: 28, index: 300 }, /* -> */ { count: 16, hostbits: 12, select: 1 }, { count: 256, hostbits: 4, select: 44 }],
+  // Index into third block
+  [{ count: 4096, netmask: 28, index: 513 }, /* -> */ { count: 16, hostbits: 12, select: 2 }, { count: 256, hostbits: 4, select: 1 }],
+  // Count too low for netmask (wasting space)
+  [{ count: 4000, netmask: 28, index: 300 }, /* -> */ { count: 16, hostbits: 12, select: 1 }, { count: 256, hostbits: 4, select: 44 }],
+])('recursive splitting when CIDR needs to be split more than 256 times: %p', (split: CidrSplit, first: CfnSplit, second: CfnSplit) => {
+  const stack = new Stack();
+  expect(stack.resolve(cidrSplitToCfnExpression('10.0.0.0/16', split))).toEqual({
+    'Fn::Select': [
+      second.select,
+      {
+        'Fn::Cidr': [
+          { 'Fn::Select': [first.select, { 'Fn::Cidr': ['10.0.0.0/16', first.count, `${first.hostbits}`] }] },
+          second.count,
+          `${second.hostbits}`,
+        ],
+      },
+    ],
+  });
+});
\ No newline at end of file