diff --git a/crates/rattler/src/install/clobber_registry.rs b/crates/rattler/src/install/clobber_registry.rs
index 3c9a62570..16426025c 100644
--- a/crates/rattler/src/install/clobber_registry.rs
+++ b/crates/rattler/src/install/clobber_registry.rs
@@ -1173,4 +1173,70 @@ mod tests {
 
         assert_check_files(&target_prefix.path().join("bin"), &["python"]);
     }
+
+    // This used to hit an expect in the clobbering code
+    #[tokio::test]
+    async fn test_directory_clobber() {
+        // Create a transaction
+        let repodata_record_with_dir = get_repodata_record(
+            get_test_data_dir().join("clobber/clobber-with-dir-0.1.0-h4616a5c_0.conda"),
+        );
+        let repodata_record_without_dir = get_repodata_record(
+            get_test_data_dir().join("clobber/clobber-without-dir-0.1.0-h4616a5c_0.conda"),
+        );
+
+        let transaction = transaction::Transaction::<PrefixRecord, RepoDataRecord> {
+            operations: vec![TransactionOperation::Install(repodata_record_with_dir)],
+            python_info: None,
+            current_python_info: None,
+            platform: Platform::current(),
+        };
+
+        // execute transaction
+        let target_prefix = tempfile::tempdir().unwrap();
+
+        let packages_dir = tempfile::tempdir().unwrap();
+        let cache = PackageCache::new(packages_dir.path());
+
+        execute_transaction(
+            transaction,
+            target_prefix.path(),
+            &reqwest_middleware::ClientWithMiddleware::from(reqwest::Client::new()),
+            &cache,
+            &InstallDriver::default(),
+            &InstallOptions::default(),
+        )
+            .await;
+
+        let prefix_records = PrefixRecord::collect_from_prefix(target_prefix.path()).unwrap();
+
+        // remove one of the clobbering files
+        let transaction = transaction::Transaction::<PrefixRecord, RepoDataRecord> {
+            operations: vec![
+                TransactionOperation::Remove(
+                    prefix_records[0].clone(),
+                ),
+                TransactionOperation::Install(repodata_record_without_dir),
+            ],
+            python_info: None,
+            current_python_info: None,
+            platform: Platform::current(),
+        };
+
+        let install_driver = InstallDriver::builder()
+            .with_prefix_records(&prefix_records)
+            .finish();
+
+        execute_transaction(
+            transaction,
+            target_prefix.path(),
+            &reqwest_middleware::ClientWithMiddleware::from(reqwest::Client::new()),
+            &cache,
+            &install_driver,
+            &InstallOptions::default(),
+        )
+            .await;
+
+        assert_check_files(&target_prefix.path(), &["dir"]);
+    }
 }
diff --git a/test-data/clobber/clobber-with-dir-0.1.0-h4616a5c_0.conda b/test-data/clobber/clobber-with-dir-0.1.0-h4616a5c_0.conda
new file mode 100644
index 000000000..339b889d0
Binary files /dev/null and b/test-data/clobber/clobber-with-dir-0.1.0-h4616a5c_0.conda differ
diff --git a/test-data/clobber/clobber-without-dir-0.1.0-h4616a5c_0.conda b/test-data/clobber/clobber-without-dir-0.1.0-h4616a5c_0.conda
new file mode 100644
index 000000000..1380136d2
Binary files /dev/null and b/test-data/clobber/clobber-without-dir-0.1.0-h4616a5c_0.conda differ
diff --git a/test-data/clobber/recipe/recipe-with-dir.yaml b/test-data/clobber/recipe/recipe-with-dir.yaml
new file mode 100644
index 000000000..29151a6ba
--- /dev/null
+++ b/test-data/clobber/recipe/recipe-with-dir.yaml
@@ -0,0 +1,23 @@
+recipe:
+  name: clobber-with-dir
+  version: 0.1.0
+
+outputs:
+  - package:
+      name: clobber-with-dir
+      version: 0.1.0
+    
+    build:
+      noarch: generic
+      script:
+        - mkdir $PREFIX/dir
+        - echo "clobber-1" > $PREFIX/dir/clobber.txt
+
+  - package:
+      name: clobber-without-dir
+      version: 0.1.0
+
+    build:
+      noarch: generic
+      script:
+        - echo "clobber-1" > $PREFIX/dir