diff --git a/.changeset/all-bats-shine.md b/.changeset/all-bats-shine.md
new file mode 100644
index 0000000000..68d86c8d15
--- /dev/null
+++ b/.changeset/all-bats-shine.md
@@ -0,0 +1,5 @@
+---
+'@backstage/cli': patch
+---
+
+Updated the WebPack configuration to use `contenthash`. This fixes an issue were builds would sometimes generate output files with the same name but different content across builds, leading to breakages when loading the frontend app.
diff --git a/packages/cli/src/modules/build/lib/bundler/config.ts b/packages/cli/src/modules/build/lib/bundler/config.ts
index bf78d04b4a..9031ce09d2 100644
--- a/packages/cli/src/modules/build/lib/bundler/config.ts
+++ b/packages/cli/src/modules/build/lib/bundler/config.ts
@@ -430,10 +430,10 @@ export async function createConfig(
       path: paths.targetDist,
       publicPath:
         options.moduleFederation?.mode === 'remote' ? 'auto' : `${publicPath}/`,
-      filename: isDev ? '[name].js' : 'static/[name].[fullhash:8].js',
+      filename: isDev ? '[name].js' : 'static/[name].[contenthash:8].js',
       chunkFilename: isDev
         ? '[name].chunk.js'
-        : 'static/[name].[chunkhash:8].chunk.js',
+        : 'static/[name].[contenthash:8].chunk.js',
       ...(isDev
         ? {
             devtoolModuleFilenameTemplate: (info: any) =>
diff --git a/packages/cli/src/modules/build/lib/bundler/optimization.ts b/packages/cli/src/modules/build/lib/bundler/optimization.ts
index 5d763ea4ac..63319ebec6 100644
--- a/packages/cli/src/modules/build/lib/bundler/optimization.ts
+++ b/packages/cli/src/modules/build/lib/bundler/optimization.ts
@@ -72,7 +72,7 @@ export const optimization = (
           },
           filename: isDev
             ? 'module-[name].js'
-            : 'static/module-[name].[chunkhash:8].js',
+            : 'static/module-[name].[contenthash:8].js',
           priority: 10,
           minSize: 100000,
           minChunks: 1,