diff --git a/src/appstate.rs b/src/appstate.rs
index 4d0a64e..f817416 100644
--- a/src/appstate.rs
+++ b/src/appstate.rs
@@ -1,4 +1,5 @@
 use std::{
+    collections::VecDeque,
     fs,
     io::{self, Write},
     path::{Path, PathBuf},
@@ -9,7 +10,7 @@ use serde::{Deserialize, Serialize};
 
 use super::{
     cli::Cli,
-    sharry::{Alias, FileChecked, FileUploading, Share},
+    sharry::{Alias, ChunkState, FileChecked, FileUploading, Share, UploadError},
 };
 
 #[derive(Serialize, Deserialize, Debug)]
@@ -19,7 +20,7 @@ pub struct AppState {
 
     alias: Alias,
     share: Share,
-    files: Vec<FileState>,
+    files: VecDeque<FileState>,
 }
 
 #[derive(Serialize, Deserialize, Debug)]
@@ -68,15 +69,15 @@ impl AppState {
             .ok()
     }
 
-    pub fn from_args(args: &Cli, agent: &ureq::Agent) -> Option<Self> {
+    pub fn from_args(args: &Cli, http: &ureq::Agent) -> Option<Self> {
         let file_name = Self::cache_file(args);
         let alias = args.get_alias();
 
-        let share = Share::create(agent, &alias, args.get_share_request())
+        let share = Share::create(http, &alias, args.get_share_request())
             .inspect_err(|e| error!("could not create Share: {e}"))
             .ok()?;
 
-        let files: Vec<_> = args.files.clone().into_iter().map(FileState::C).collect();
+        let files: VecDeque<_> = args.files.clone().into_iter().map(FileState::C).collect();
 
         Some(Self {
             file_name,
@@ -86,6 +87,41 @@ impl AppState {
         })
     }
 
+    pub fn upload_chunk(
+        &mut self,
+        http: &ureq::Agent,
+        chunk_size: usize,
+    ) -> Result<Option<()>, UploadError> {
+        let uploading = match self.files.pop_front() {
+            Some(FileState::C(checked)) => checked
+                .start_upload(http, &self.alias, &self.share)
+                .unwrap(),
+            Some(FileState::U(uploading)) => uploading,
+            None => {
+                self.share.notify(http, &self.alias).unwrap();
+
+                return Ok(None);
+            }
+        };
+
+        debug!("{uploading} chunk {chunk_size}");
+
+        match uploading.upload_chunk(http, &self.alias, chunk_size) {
+            ChunkState::Ok(upl) => {
+                self.files.push_front(FileState::U(upl));
+                Ok(Some(()))
+            }
+            ChunkState::Err(upl, e) => {
+                self.files.push_front(FileState::U(upl));
+                Err(e)
+            }
+            ChunkState::Finished(path) => {
+                debug!("Finished {:?}!", path.display());
+                Ok(Some(()))
+            }
+        }
+    }
+
     pub fn save(&self) -> io::Result<()> {
         fs::create_dir_all(Self::cache_dir())?;
 
diff --git a/src/main.rs b/src/main.rs
index 2609c20..eb52dbe 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -3,12 +3,11 @@ mod cli;
 mod sharry;
 
 use clap::Parser;
-use log::{debug, error, info};
+use log::{error, info};
 use ureq::Agent;
 
 use appstate::AppState;
 use cli::Cli;
-use sharry::{ChunkState, Share};
 
 fn main() {
     env_logger::init();
@@ -22,7 +21,7 @@ fn main() {
         .build()
         .into();
 
-    let state = AppState::try_resume(&args)
+    let mut state = AppState::try_resume(&args)
         .map(|state| {
             info!("loaded state: {state:?}");
 
@@ -37,34 +36,17 @@ fn main() {
 
     info!("continuing with state: {state:?}");
     state.save().unwrap();
-    // state.clear().unwrap();
 
-    return;
-
-    let alias = args.get_alias();
-    let share = Share::create(&agent, &alias, args.get_share_request()).unwrap();
-    info!("share: {share:?}");
-
-    for file in args.files {
-        let mut file = file.start_upload(&agent, &alias, &share).unwrap();
-        info!("file: {file:?}");
-
-        loop {
-            match file.upload_chunk(&agent, &alias, args.chunk_size * 1024 * 1024) {
-                ChunkState::Ok(upl) => file = upl,
-                ChunkState::Err(upl, e) => {
-                    error!("error: {e:?}");
-                    file = upl;
-                }
-                ChunkState::Finished(path) => {
-                    info!("Finished {:?}!", path.display());
-                    break;
-                }
-            }
-
-            debug!("file: {file:?}");
+    loop {
+        match state.upload_chunk(&agent, args.chunk_size * 1024 * 1024) {
+            Ok(None) => break,
+            Err(e) => error!("error: {e:?}"),
+            _ => (),
         }
-    }
 
-    share.notify(&agent, &alias).unwrap();
+        state.save().unwrap();
+    }
+    info!("uploads done");
+
+    state.clear().unwrap();
 }
diff --git a/src/sharry/file/mod.rs b/src/sharry/file/mod.rs
index f9d6c3b..4614561 100644
--- a/src/sharry/file/mod.rs
+++ b/src/sharry/file/mod.rs
@@ -2,6 +2,6 @@ mod checked;
 mod uploading;
 
 pub use checked::FileChecked;
-pub use uploading::{ChunkState, FileUploading};
+pub use uploading::{ChunkState, FileUploading, UploadError};
 
 use super::{Alias, Share, alias::SharryAlias};
diff --git a/src/sharry/file/uploading.rs b/src/sharry/file/uploading.rs
index 7cfd393..c881bf5 100644
--- a/src/sharry/file/uploading.rs
+++ b/src/sharry/file/uploading.rs
@@ -1,4 +1,5 @@
 use std::{
+    fmt::Display,
     fs::File,
     io::{self, Read, Seek, SeekFrom},
     path::PathBuf,
@@ -35,6 +36,16 @@ pub enum ChunkState {
     Finished(PathBuf),
 }
 
+impl Display for FileUploading {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        write!(
+            f,
+            "Uploading ({:?}, {}, {})",
+            self.path, self.size, self.offset
+        )
+    }
+}
+
 impl FileUploading {
     pub(super) fn new(path: PathBuf, size: usize, uri: String) -> Self {
         Self {