diff --git a/packages/cli-opt/src/file.rs b/packages/cli-opt/src/file.rs
index 5c0e462174..16ae754e3d 100644
--- a/packages/cli-opt/src/file.rs
+++ b/packages/cli-opt/src/file.rs
@@ -97,7 +97,8 @@ pub(crate) fn process_file_to_with_options(
     }
 
     // If everything was successful, rename the temp file to the final output path
-    std::fs::rename(temp_path, output_path).context("Failed to rename output file")?;
+    std::fs::rename(temp_path, output_path)
+        .with_context(|| format!("Failed to rename output file to: {}", output_path.display()))?;
 
     Ok(())
 }
diff --git a/packages/cli-opt/src/hash.rs b/packages/cli-opt/src/hash.rs
index 79cfb2b8e4..05163e050e 100644
--- a/packages/cli-opt/src/hash.rs
+++ b/packages/cli-opt/src/hash.rs
@@ -152,7 +152,10 @@ pub fn add_hash_to_asset(asset: &mut BundledAsset) {
             };
 
             if let Some(ext) = ext {
-                bundled_path.set_extension(ext);
+                // Push the extension to the bundled path. There may be multiple extensions (e.g. .js.map)
+                // with one left after the file_stem is extracted above so we need to push the extension
+                // instead of setting it
+                bundled_path.as_mut_os_string().push(format!(".{ext}"));
             }
 
             let bundled_path = bundled_path.to_string_lossy().to_string();
diff --git a/packages/cli-opt/src/lib.rs b/packages/cli-opt/src/lib.rs
index c52313527d..b84252a211 100644
--- a/packages/cli-opt/src/lib.rs
+++ b/packages/cli-opt/src/lib.rs
@@ -79,9 +79,14 @@ impl AssetManifest {
             .is_some_and(|assets| assets.contains(asset))
     }
 
-    /// Iterate over all the assets in the manifest
-    pub fn assets(&self) -> impl Iterator<Item = &BundledAsset> {
-        self.assets.values().flat_map(|assets| assets.iter())
+    /// Iterate over all the assets with unique output paths in the manifest. This will not include
+    /// assets that have different source paths, but the same file contents.
+    pub fn unique_assets(&self) -> impl Iterator<Item = &BundledAsset> {
+        let mut seen = HashSet::new();
+        self.assets
+            .values()
+            .flat_map(|assets| assets.iter())
+            .filter(move |asset| seen.insert(asset.bundled_path()))
     }
 
     pub fn load_from_file(path: &Path) -> anyhow::Result<Self> {
diff --git a/packages/cli/src/build/builder.rs b/packages/cli/src/build/builder.rs
index 84f8df388a..8b00b24c97 100644
--- a/packages/cli/src/build/builder.rs
+++ b/packages/cli/src/build/builder.rs
@@ -637,7 +637,7 @@ impl AppBuilder {
         let asset_dir = self.build.asset_dir();
 
         // Hotpatch asset!() calls
-        for bundled in res.assets.assets() {
+        for bundled in res.assets.unique_assets() {
             let original_artifacts = self
                 .artifacts
                 .as_mut()
diff --git a/packages/cli/src/build/request.rs b/packages/cli/src/build/request.rs
index 51e6e189a0..b398fed121 100644
--- a/packages/cli/src/build/request.rs
+++ b/packages/cli/src/build/request.rs
@@ -1189,7 +1189,7 @@ impl BuildRequest {
 
         // Create a set of all the paths that new files will be bundled to
         let mut keep_bundled_output_paths: HashSet<_> = assets
-            .assets()
+            .unique_assets()
             .map(|a| asset_dir.join(a.bundled_path()))
             .collect();
 
@@ -1228,7 +1228,7 @@ impl BuildRequest {
         let mut assets_to_transfer = vec![];
 
         // Queue the bundled assets
-        for bundled in assets.assets() {
+        for bundled in assets.unique_assets() {
             let from = PathBuf::from(bundled.absolute_source_path());
             let to = asset_dir.join(bundled.bundled_path());
 
@@ -4310,7 +4310,7 @@ __wbg_init({{module_or_path: "/{}/{wasm_path}"}}).then((wasm) => {{
         }
 
         // Inject any resources from manganis into the head
-        for asset in assets.assets() {
+        for asset in assets.unique_assets() {
             let asset_path = asset.bundled_path();
             match asset.options().variant() {
                 AssetVariant::Css(css_options) => {
diff --git a/packages/cli/src/cli/build_assets.rs b/packages/cli/src/cli/build_assets.rs
index f8688b2caf..4023d58f46 100644
--- a/packages/cli/src/cli/build_assets.rs
+++ b/packages/cli/src/cli/build_assets.rs
@@ -19,7 +19,7 @@ impl BuildAssets {
         let manifest = extract_assets_from_file(&self.executable)?;
 
         create_dir_all(&self.destination)?;
-        for asset in manifest.assets() {
+        for asset in manifest.unique_assets() {
             let source_path = PathBuf::from(asset.absolute_source_path());
             let destination_path = self.destination.join(asset.bundled_path());
             debug!(