diff --git a/packages/aws-cdk-lib/core/lib/cfn-fn.ts b/packages/aws-cdk-lib/core/lib/cfn-fn.ts
index 2441aaabe56a0..01b235a67d13b 100644
--- a/packages/aws-cdk-lib/core/lib/cfn-fn.ts
+++ b/packages/aws-cdk-lib/core/lib/cfn-fn.ts
@@ -275,7 +275,10 @@ export class Fn {
     if (conditions.length === 1) {
       return conditions[0] as ICfnRuleConditionExpression;
     }
-    return Fn.conditionAnd(..._inGroupsOf(conditions, 10).map(group => new FnAnd(...group)));
+    if (conditions.length <= 10) {
+      return new FnAnd(...conditions);
+    }
+    return Fn.conditionAnd(..._inGroupsOf(conditions, 10).map(group => Fn.conditionAnd(...group)));
   }
 
   /**
diff --git a/packages/aws-cdk-lib/core/test/condition.test.ts b/packages/aws-cdk-lib/core/test/condition.test.ts
index cfb5670394122..db7c8af4dfd10 100644
--- a/packages/aws-cdk-lib/core/test/condition.test.ts
+++ b/packages/aws-cdk-lib/core/test/condition.test.ts
@@ -60,6 +60,106 @@ describe('condition', () => {
     });
   });
 
+  test('condition length is 10n + 1 in Fn.conditionAnd', () => {
+    // GIVEN
+    const stack = new cdk.Stack();
+    const expression = cdk.Fn.conditionAnd(
+      cdk.Fn.conditionEquals('a', '1'),
+      cdk.Fn.conditionEquals('b', '2'),
+      cdk.Fn.conditionEquals('c', '3'),
+      cdk.Fn.conditionEquals('d', '4'),
+      cdk.Fn.conditionEquals('e', '5'),
+      cdk.Fn.conditionEquals('f', '6'),
+      cdk.Fn.conditionEquals('g', '7'),
+      cdk.Fn.conditionEquals('h', '8'),
+      cdk.Fn.conditionEquals('i', '9'),
+      cdk.Fn.conditionEquals('j', '10'),
+      cdk.Fn.conditionEquals('k', '11'),
+    );
+
+    // WHEN
+    new cdk.CfnCondition(stack, 'Condition', { expression });
+
+    // THEN
+    expect(toCloudFormation(stack)).toEqual({
+      Conditions: {
+        Condition: {
+          'Fn::And': [
+            {
+              'Fn::And': [
+                { 'Fn::Equals': ['a', '1'] },
+                { 'Fn::Equals': ['b', '2'] },
+                { 'Fn::Equals': ['c', '3'] },
+                { 'Fn::Equals': ['d', '4'] },
+                { 'Fn::Equals': ['e', '5'] },
+                { 'Fn::Equals': ['f', '6'] },
+                { 'Fn::Equals': ['g', '7'] },
+                { 'Fn::Equals': ['h', '8'] },
+                { 'Fn::Equals': ['i', '9'] },
+                { 'Fn::Equals': ['j', '10'] },
+              ],
+            },
+            {
+              'Fn::Equals': ['k', '11'],
+            },
+          ],
+        },
+      },
+    });
+  });
+
+  test('condition length is more than 10 in Fn.conditionAnd', () => {
+    // GIVEN
+    const stack = new cdk.Stack();
+    const expression = cdk.Fn.conditionAnd(
+      cdk.Fn.conditionEquals('a', '1'),
+      cdk.Fn.conditionEquals('b', '2'),
+      cdk.Fn.conditionEquals('c', '3'),
+      cdk.Fn.conditionEquals('d', '4'),
+      cdk.Fn.conditionEquals('e', '5'),
+      cdk.Fn.conditionEquals('f', '6'),
+      cdk.Fn.conditionEquals('g', '7'),
+      cdk.Fn.conditionEquals('h', '8'),
+      cdk.Fn.conditionEquals('i', '9'),
+      cdk.Fn.conditionEquals('j', '10'),
+      cdk.Fn.conditionEquals('k', '11'),
+      cdk.Fn.conditionEquals('l', '12'),
+    );
+
+    // WHEN
+    new cdk.CfnCondition(stack, 'Condition', { expression });
+
+    // THEN
+    expect(toCloudFormation(stack)).toEqual({
+      Conditions: {
+        Condition: {
+          'Fn::And': [
+            {
+              'Fn::And': [
+                { 'Fn::Equals': ['a', '1'] },
+                { 'Fn::Equals': ['b', '2'] },
+                { 'Fn::Equals': ['c', '3'] },
+                { 'Fn::Equals': ['d', '4'] },
+                { 'Fn::Equals': ['e', '5'] },
+                { 'Fn::Equals': ['f', '6'] },
+                { 'Fn::Equals': ['g', '7'] },
+                { 'Fn::Equals': ['h', '8'] },
+                { 'Fn::Equals': ['i', '9'] },
+                { 'Fn::Equals': ['j', '10'] },
+              ],
+            },
+            {
+              'Fn::And': [
+                { 'Fn::Equals': ['k', '11'] },
+                { 'Fn::Equals': ['l', '12'] },
+              ],
+            },
+          ],
+        },
+      },
+    });
+  });
+
   test('condition length is 10n + 1 in Fn.conditionOr', () => {
     // GIVEN
     const stack = new cdk.Stack();