diff --git a/packages/cdkConstructs/src/changesets/checkDestructiveChanges.ts b/packages/cdkConstructs/src/changesets/checkDestructiveChanges.ts
index 0f8807d5..84ab85ba 100644
--- a/packages/cdkConstructs/src/changesets/checkDestructiveChanges.ts
+++ b/packages/cdkConstructs/src/changesets/checkDestructiveChanges.ts
@@ -5,6 +5,16 @@ import {
   Change as CloudFormationChange
 } from "@aws-sdk/client-cloudformation"
 
+const isConditionalCdkMetadataChange = (resourceChange: CloudFormationChange["ResourceChange"]): boolean => {
+  if (!resourceChange) {
+    return false
+  }
+
+  return resourceChange.LogicalResourceId === "CDKMetadata" &&
+    resourceChange.ResourceType === "AWS::CDK::Metadata" &&
+    String(resourceChange.Replacement ?? "") === "Conditional"
+}
+
 export type ChangeRequiringAttention = {
   logicalId: string;
   physicalId: string;
@@ -66,6 +76,10 @@ export function checkDestructiveChanges(
       const action = resourceChange.Action
       const isRemoval = action === "Remove"
 
+      if (replacementNeeded && isConditionalCdkMetadataChange(resourceChange)) {
+        return undefined
+      }
+
       if (!replacementNeeded && !isRemoval) {
         return undefined
       }
diff --git a/packages/cdkConstructs/tests/changesets/checkDestructiveChanges.test.ts b/packages/cdkConstructs/tests/changesets/checkDestructiveChanges.test.ts
index 7cdb31bd..ab83f783 100644
--- a/packages/cdkConstructs/tests/changesets/checkDestructiveChanges.test.ts
+++ b/packages/cdkConstructs/tests/changesets/checkDestructiveChanges.test.ts
@@ -100,6 +100,25 @@ describe("checkDestructiveChanges", () => {
       }
     ])
   })
+
+  test("ignores conditional CDK metadata replacements", () => {
+    const changeSet = {
+      Changes: [
+        {
+          ResourceChange: {
+            LogicalResourceId: "CDKMetadata",
+            PhysicalResourceId: "metadata-id",
+            ResourceType: "AWS::CDK::Metadata",
+            Replacement: "Conditional"
+          }
+        }
+      ]
+    }
+
+    const replacements = checkDestructiveChanges(changeSet)
+
+    expect(replacements).toEqual([])
+  })
 })
 
 describe("checkDestructiveChangeSet", () => {