diff --git a/src/local.rs b/src/local.rs
index 1e9e132..d31e746 100644
--- a/src/local.rs
+++ b/src/local.rs
@@ -17,12 +17,49 @@ struct InfoPayload {
     app_version: u32,
 }
 
+macro_rules! multi_error {
+    ($name:tt { $($variant:tt($t:ty)),+ $(,)? }) => {
+        #[derive(Debug)]
+        pub enum $name {
+            $($variant($t)),+
+        }
+
+        impl ::std::fmt::Display for $name {
+            fn fmt(&self, f: &mut ::std::fmt::Formatter<'_>) -> ::std::fmt::Result {
+                match self {
+                    $(
+                        Self::$variant(x) => x.fmt(f)
+                    ),+
+                }
+            }
+        }
+
+        impl ::std::error::Error for $name {}
+
+        $(
+            impl From<$t> for $name {
+                fn from(value: $t) -> Self {
+                    Self::$variant(value)
+                }
+            }
+        )+
+    };
+}
+
+multi_error!(
+    Error {
+        Io(std::io::Error),
+        Http(reqwest::Error),
+    }
+);
+
+/// Represents a connection to the server running on the mobile device.
 pub struct LocalServer {
     base_uri: reqwest::Url,
     info: InfoPayload,
     client: reqwest::Client,
     cache: FileCache,
-    tasks: JoinSet<reqwest::Result<()>>,
+    tasks: JoinSet<Result<(), Error>>,
     semaphore: Arc<Semaphore>,
 }
 
@@ -72,10 +109,6 @@ impl LocalServer {
         path: impl AsRef<Path>,
     ) -> Result<(), Box<dyn std::error::Error>> {
         let path = path.as_ref();
-        let fd = tokio::fs::OpenOptions::new()
-            .read(true)
-            .open(path.to_owned())
-            .await?;
         if !self.should_upload(path) {
             return Err(Box::new(std::io::Error::new(
                 std::io::ErrorKind::InvalidInput,
@@ -83,10 +116,6 @@ impl LocalServer {
             )));
         }
         let filename = path.file_name().unwrap().to_string_lossy().to_string();
-
-        let form = multipart::Form::new()
-            .part("filename", multipart::Part::text(filename.to_string()))
-            .part("file", multipart::Part::stream(fd).file_name(filename));
         let client = self.client.clone();
         let base_uri = self.base_uri.clone();
         let semaphore = self.semaphore.clone();
@@ -96,6 +125,14 @@ impl LocalServer {
         // The actual upload task
         self.tasks.spawn(async move {
             let _permit = semaphore.acquire_owned().await.unwrap();
+            let fd = tokio::fs::OpenOptions::new()
+                .read(true)
+                .open(path.to_owned())
+                .await?;
+
+            let form = multipart::Form::new()
+                .part("filename", multipart::Part::text(filename.to_string()))
+                .part("file", multipart::Part::stream(fd).file_name(filename));
             let response = client
                 .post(base_uri.join("upload").unwrap())
                 .multipart(form)
@@ -110,7 +147,7 @@ impl LocalServer {
                 info!("Uploaded {}.", path.display());
             }
 
-            reqwest::Result::Ok(())
+            Ok(())
         });
 
         Ok(())
@@ -118,7 +155,7 @@ impl LocalServer {
 
     /// Provides an awaitable function for the task queue. This function will
     /// only return once the queue is empty or if an error occurs.
-    pub async fn wait_on_queue(&mut self) -> reqwest::Result<()> {
+    pub async fn wait_on_queue(&mut self) -> Result<(), Error> {
         while let Some(task) = self.tasks.join_next().await {
             task.expect("upload task spawn error")?;
         }