diff --git a/src/playlist.rs b/src/playlist.rs
index 8f42b16..b6a0876 100644
--- a/src/playlist.rs
+++ b/src/playlist.rs
@@ -67,7 +67,7 @@ impl<'a> Playlist<'a> {
 
         drop(writer);
         let output = output.into_inner()?;
-        if fs::read(&path)? != output {
+        if !path.exists() || fs::read(&path)? != output {
             fs::write(path, output.as_slice())?;
             Ok(true)
         } else {
diff --git a/src/sync.rs b/src/sync.rs
index 9bc0d83..6840b4c 100644
--- a/src/sync.rs
+++ b/src/sync.rs
@@ -162,6 +162,7 @@ pub(crate) fn sync(
 
             if !target.exists() {
                 println!("[info] copying from {:?} to {:?}.", source, target);
+                fs::create_dir_all(target.parent().unwrap())?;
                 fs::copy(source, target)?;
             }
         }