diff --git a/rojo-test/syncback-test-snapshots/end_to_end__rojo_test__syncback_util__slugified_name-stdout.snap b/rojo-test/syncback-test-snapshots/end_to_end__rojo_test__syncback_util__slugified_name-stdout.snap
index b50c2448..13188a47 100644
--- a/rojo-test/syncback-test-snapshots/end_to_end__rojo_test__syncback_util__slugified_name-stdout.snap
+++ b/rojo-test/syncback-test-snapshots/end_to_end__rojo_test__syncback_util__slugified_name-stdout.snap
@@ -7,8 +7,7 @@ Writing default.project.json
 Writing src/Camera.rbxm
 Writing src/Terrain.rbxm
 Writing src/_Folder/init.meta.json
-Writing src/_Script/init.meta.json
-Writing src/_Script/init.server.luau
+Writing src/_Script.meta.json
+Writing src/_Script.server.luau
 Writing src
 Writing src/_Folder
-Writing src/_Script
diff --git a/src/syncback/mod.rs b/src/syncback/mod.rs
index 57d86f24..8e0d7d03 100644
--- a/src/syncback/mod.rs
+++ b/src/syncback/mod.rs
@@ -360,16 +360,25 @@ pub fn get_best_middleware(snapshot: &SyncbackSnapshot) -> Middleware {
         }
     }
 
-    // If the instance name is invalid for the filesystem, use directory middleware
-    // to allow preserving the name in meta.json
+    // If the name is invalid but the instance has no descendants and isn't a
+    // folder/config/tool, prefer slugified files over creating a directory.
+    // Only promote to directory when there are children (or dir-like classes).
     if crate::syncback::file_names::validate_file_name(&inst.name).is_err() {
         middleware = match middleware {
-            Middleware::ServerScript => Middleware::ServerScriptDir,
-            Middleware::ClientScript => Middleware::ClientScriptDir,
-            Middleware::ModuleScript => Middleware::ModuleScriptDir,
-            Middleware::Csv => Middleware::CsvDir,
-            Middleware::JsonModel | Middleware::Text => Middleware::Dir,
-            _ => middleware,
+            Middleware::ServerScript | Middleware::ClientScript | Middleware::ModuleScript
+                if inst.children().is_empty() =>
+            {
+                middleware
+            }
+            Middleware::JsonModel | Middleware::Text if inst.children().is_empty() => middleware,
+            _ => match middleware {
+                Middleware::ServerScript => Middleware::ServerScriptDir,
+                Middleware::ClientScript => Middleware::ClientScriptDir,
+                Middleware::ModuleScript => Middleware::ModuleScriptDir,
+                Middleware::Csv => Middleware::CsvDir,
+                Middleware::JsonModel | Middleware::Text => Middleware::Dir,
+                _ => middleware,
+            },
         }
     }
 
diff --git a/tests/tests/syncback.rs b/tests/tests/syncback.rs
index e2b1f6f5..10be92a8 100644
--- a/tests/tests/syncback.rs
+++ b/tests/tests/syncback.rs
@@ -87,8 +87,8 @@ syncback_tests! {
     // Ensures that the `syncUnscriptable` setting works
     unscriptable_properties => ["default.project.json"],
     // Ensures that instances with names containing illegal characters get slugified filenames
-    // and preserve their original names in meta.json
-    slugified_name => ["src/_Script/init.meta.json", "src/_Script/init.server.luau", "src/_Folder/init.meta.json"],
+    // and preserve their original names in meta.json without forcing directories for leaf scripts
+    slugified_name => ["src/_Script.meta.json", "src/_Script.server.luau", "src/_Folder/init.meta.json"],
     // Ensures that .model.json files preserve the name property
     model_json_name => ["src/foo.model.json"],
 }