diff --git a/src/dev-generation.ts b/src/dev-generation.ts
index c4d30b6c..5cf1c51b 100644
--- a/src/dev-generation.ts
+++ b/src/dev-generation.ts
@@ -494,9 +494,11 @@ export const createReactRouterDevRuntime = ({
         if (cssAssetsRemoved) {
           reloadAfterCssRemoval = !cssAssetsAdded;
           notifyCssAssetOwnershipChanged();
-        } else if (webChanged && reloadAfterCssRemoval) {
+        } else if (cssAssetsAdded) {
+          if (reloadAfterCssRemoval) {
+            notifyCssAssetOwnershipChanged();
+          }
           reloadAfterCssRemoval = false;
-          notifyCssAssetOwnershipChanged();
         }
       } catch (cause) {
         rejectAttempt(
diff --git a/tests/dev-generation.test.ts b/tests/dev-generation.test.ts
index 500adfee..6a129382 100644
--- a/tests/dev-generation.test.ts
+++ b/tests/dev-generation.test.ts
@@ -406,6 +406,19 @@ describe('React Router development runtime', () => {
       cssOnlyChange,
       graphIdentity(removedCssWeb, node)
     );
+    expect(onCssAssetOwnershipChanged).toHaveBeenCalledOnce();
+
+    const contentOnlyWeb = createCompilation('web');
+    runtime.beginAttempt();
+    captureWeb(runtime, contentOnlyWeb, 'without-css-content-edit', {
+      routes: { 'routes/about': [] },
+    });
+    await runtime.finishAttempt(
+      createGraphStats(contentOnlyWeb, node),
+      cssOnlyChange,
+      graphIdentity(contentOnlyWeb, node)
+    );
+    expect(onCssAssetOwnershipChanged).toHaveBeenCalledOnce();
 
     const readdedCssWeb = createCompilation('web');
     runtime.beginAttempt();