diff --git a/src/appstate.rs b/src/appstate.rs
index e253e53..8ce7180 100644
--- a/src/appstate.rs
+++ b/src/appstate.rs
@@ -11,7 +11,7 @@ use log::{debug, warn};
 use super::{
     cachefile::CacheFile,
     cli::Cli,
-    file::{self, FileTrait, Chunk},
+    file::{self, Chunk, FileTrait},
     sharry::{self, Client},
 };
 
@@ -162,6 +162,18 @@ 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");
+            return None;
+        };
+
+        let uploading = uploading.rewind()?;
+        self.inner.push_file(uploading);
+
+        Some(self)
+    }
+
     pub fn file_names(&self) -> Vec<&str> {
         self.inner.file_names()
     }
diff --git a/src/file/uploading.rs b/src/file/uploading.rs
index dc40d86..0b2118f 100644
--- a/src/file/uploading.rs
+++ b/src/file/uploading.rs
@@ -4,6 +4,7 @@ use std::{
     path::PathBuf,
 };
 
+use log::warn;
 use serde::{Deserialize, Serialize};
 
 use super::{Chunk, FileTrait};
@@ -45,11 +46,17 @@ impl Uploading {
     }
 
     pub fn rewind(self) -> Option<Self> {
-        self.last_offset.map(|last_offset| Self {
-            last_offset: None,
-            offset: last_offset,
-            ..self
-        })
+        match self.last_offset {
+            Some(last_offset) => Some(Self {
+                last_offset: None,
+                offset: last_offset,
+                ..self
+            }),
+            None => {
+                warn!("attempted to rewind twice");
+                None
+            }
+        }
     }
 
     pub fn read<'t>(&mut self, buf: &'t mut [u8]) -> io::Result<Chunk<'t>> {
diff --git a/src/main.rs b/src/main.rs
index 9477a8a..dcfa946 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -117,7 +117,17 @@ fn main() {
 
     loop {
         match state.upload_chunk(&mut buffer) {
-            Err(e) => error!("error: {e:?}"), // HACK handle errors better
+            Err(e) => {
+                // HACK handle errors better
+                error!("error: {e:?}");
+
+                if let Some(s) = state.rewind() {
+                    state = s;
+                } else {
+                    eprintln!("{} Failed to retry chunk!", style("Error:").red().bold());
+                    process::exit(1);
+                };
+            }
             Ok(true) => {
                 info!("all uploads done");
                 state.clear().unwrap_or_else(|e| {