diff --git a/src/appstate.rs b/src/appstate.rs
index 8fb5252..68eff53 100644
--- a/src/appstate.rs
+++ b/src/appstate.rs
@@ -9,7 +9,7 @@ use indicatif::{ProgressBar, ProgressStyle};
 use log::{debug, warn};
 
 use crate::{
-    cachefile::CacheFile,
+    cachefile::{CacheFile, FileState},
     cli::Cli,
     file::{self, Chunk, FileTrait},
     sharry::{self, Client},
@@ -153,14 +153,23 @@ impl AppState {
         Ok(self.is_done())
     }
 
-    pub fn rewind(mut self) -> Option<Self> {
-        let Some(uploading) = self.inner.pop_file(&self.http) else {
-            warn!("rewind called on empty queue");
+    pub fn rewind_chunk(mut self) -> Option<Self> {
+        let uploading = if let Some(state) = self.inner.pop_file() {
+            match state {
+                FileState::U(s) => s,
+                FileState::C(s) => {}
+            }
+        } else {
+            warn!("rewind_chunk called on empty queue");
             return None;
         };
 
-        let uploading = uploading.rewind()?;
-        self.inner.push_file(uploading);
+        let Some(FileState::U(uploading)) = self.inner.pop_file() else {
+            warn!("rewind_chunk called in invalid state");
+            return None;
+        };
+
+        self.inner.push_file(FileState::U(uploading.rewind()?));
 
         Some(self)
     }
@@ -179,6 +188,14 @@ impl AppState {
         Some(self)
     }
 
+    pub fn rebuild_share(self, args: &Cli) -> sharry::Result<Self> {
+        let share_id =
+            self.http
+                .share_create(&args.get_uri(), &args.alias, args.get_share_request())?;
+
+        Ok(Self::new(self.http, CacheFile::from_args(args, share_id)))
+    }
+
     pub fn file_names(&self) -> Vec<&str> {
         self.inner.file_names()
     }
diff --git a/src/cachefile.rs b/src/cachefile.rs
index 44d07a0..022244e 100644
--- a/src/cachefile.rs
+++ b/src/cachefile.rs
@@ -14,34 +14,6 @@ use crate::{
     sharry::{self, Client, Uri},
 };
 
-#[derive(Serialize, Deserialize, Debug)]
-enum FileState {
-    C(file::Checked),
-    U(file::Uploading),
-}
-
-impl FileState {
-    fn file_name(&self) -> &str {
-        match self {
-            FileState::C(c) => c.get_name(),
-            FileState::U(u) => u.get_name(),
-        }
-    }
-
-    fn start_upload(
-        self,
-        client: &impl sharry::Client,
-        uri: &sharry::Uri,
-        alias_id: &str,
-        share_id: &str,
-    ) -> sharry::Result<file::Uploading> {
-        match self {
-            FileState::C(checked) => checked.start_upload(client, uri, alias_id, share_id),
-            FileState::U(uploading) => Ok(uploading),
-        }
-    }
-}
-
 #[derive(Serialize, Deserialize, Debug)]
 pub struct CacheFile {
     #[serde(skip)]
@@ -50,7 +22,9 @@ pub struct CacheFile {
     uri: Uri,
     alias_id: String,
     share_id: String,
-    files: VecDeque<FileState>,
+
+    uploading: Option<file::Uploading>,
+    files: VecDeque<file::Checked>,
 }
 
 impl CacheFile {
@@ -88,38 +62,47 @@ impl CacheFile {
             uri: args.get_uri(),
             alias_id: args.alias.clone(),
             share_id,
-            files: args.files.clone().into_iter().map(FileState::C).collect(),
+            uploading: None,
+            files: args.files.clone().into(),
         }
     }
 
     pub fn file_names(&self) -> Vec<&str> {
-        self.files.iter().map(FileState::file_name).collect()
+        let mut result = vec![];
+
+        if let Some(upl) = self.uploading.as_ref() {
+            result.push(upl.get_name());
+        }
+        self.files.iter().map(|chk| result.push(chk.get_name()));
+
+        result
     }
 
-    pub fn is_empty(&self) -> bool {
-        self.files.is_empty()
-    }
+    pub fn start_upload(&mut self, client: &impl Client) -> sharry::Result<bool> {
+        if self.uploading.is_some() {
+            return Ok(true);
+        }
 
-    pub fn pop_file(&mut self, client: &impl Client) -> Option<file::Uploading> {
-        if let Some(state) = self.files.pop_front() {
-            // HACK unwrap
-            // TODO somehow retry
-            Some(
-                state
-                    .start_upload(client, &self.uri, &self.alias_id, &self.share_id)
-                    .unwrap(),
-            )
+        if let Some(chk) = self.files.pop_front() {
+            self.uploading =
+                Some(chk.start_upload(client, &self.uri, &self.alias_id, &self.share_id)?);
+
+            Ok(true)
         } else {
-            None
+            Ok(false)
         }
     }
 
-    pub fn push_file(&mut self, file: file::Uploading) {
-        self.files.push_front(FileState::U(file));
+    pub fn uploading(&mut self) -> &mut Option<file::Uploading> {
+        &mut self.uploading
     }
 
-    pub fn requeue_file(&mut self, file: file::Checked) {
-        self.files.push_back(FileState::C(file));
+    pub fn abort_upload(&mut self) {
+        let Some(upl) = self.uploading.take() else {
+            panic!("abort called while not uploading");
+        };
+
+        self.files.push_front(upl.abort());
     }
 
     pub fn share_notify(&self, client: &impl Client) -> sharry::Result<()> {
diff --git a/src/main.rs b/src/main.rs
index de85892..9d3ef63 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -88,7 +88,6 @@ fn main() {
         match state.upload_chunk(&mut buffer) {
             Err(e) => {
                 Log::handle(&e);
-                tries += 1;
 
                 match e {
                     ClientError::InvalidParameter(p) => match p {
@@ -99,22 +98,29 @@ fn main() {
                                 Log::error("Failed to requeue file!");
                             };
 
-                            trace!("File {fid:?} requeued (tried: {tries})");
+                            trace!("File {fid:?} requeued");
                             state = s;
                         }
-                        // TODO Error 404: Share might have been deleted
+                        // TODO Error 404: Share not found
                         Parameter::ShareID(sid) => {
-                            Log::error(format_args!("404 sid: {sid}"));
+                            // requeue file
+                            let Ok(s) = state.rebuild_share(&args) else {
+                                Log::error("Failed to rebuild share!");
+                            };
+
+                            trace!("Share {sid:?} rebuilt");
+                            state = s;
                         }
                         p => Log::error(format_args!("Unexpected {p}!")),
                     },
                     _ => {
                         // retry chunk
-                        let Some(s) = state.rewind() else {
+                        let Some(s) = state.rewind_chunk() else {
                             Log::error("Failed to retry chunk!");
                         };
+                        tries += 1;
 
-                        trace!("State rewound, retrying last chunk (tried: {tries})");
+                        trace!("State rewound, retrying last chunk (tries: {tries})");
                         state = s;
                     }
                 }