diff --git a/src/main.rs b/src/main.rs
index 073177e..401cdbb 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -193,20 +193,34 @@ impl StateInner {
             .to_str()
             .ok_or(eyre::eyre!("Filename is not valid utf8"))?;
 
-        let file = tokio::fs::File::open(path).await?;
+        let mut retries = 0;
 
-        let body = Body::builder()
-            .append(Part::new("images[]", file).filename(filename))
-            .build();
+        let mut response = loop {
+            let file = tokio::fs::File::open(path).await?;
 
-        let mut response = self
-            .client
-            .post(self.upload_endpoint())
-            .insert_header((CONTENT_TYPE, body.content_type()))
-            .timeout(Duration::from_secs(60))
-            .send_stream(body)
-            .await
-            .map_err(|e| eyre::eyre!("Error sending request {e}"))?;
+            let body = Body::builder()
+                .append(Part::new("images[]", file).filename(filename))
+                .build();
+
+            let res = self
+                .client
+                .post(self.upload_endpoint())
+                .insert_header((CONTENT_TYPE, body.content_type()))
+                .timeout(Duration::from_secs(60))
+                .send_stream(body)
+                .await;
+
+            match res {
+                Ok(response) => break response,
+                Err(e) if retries < 10 => {
+                    retries += 1;
+                    tracing::warn!("Failed upload with {e}, retrying +{retries}");
+                }
+                Err(e) => {
+                    return Err(eyre::eyre!("Failed upload with {e}"));
+                }
+            }
+        };
 
         let response: UploadReponse = response.json().await?;
 
@@ -233,14 +247,28 @@ impl StateInner {
         let claim_endpoint = self.claim_endpoint();
 
         let mut response = loop {
-            let response = self
-                .client
-                .get(&claim_endpoint)
-                .query(upload)?
-                .timeout(Duration::from_secs(20))
-                .send()
-                .await
-                .map_err(|e| eyre::eyre!("Error sending request {e}"))?;
+            let mut retries = 0;
+
+            let response = loop {
+                let res = self
+                    .client
+                    .get(&claim_endpoint)
+                    .query(upload)?
+                    .timeout(Duration::from_secs(20))
+                    .send()
+                    .await;
+
+                match res {
+                    Ok(response) => break response,
+                    Err(e) if retries < 10 => {
+                        retries += 1;
+                        tracing::warn!("Failed claim with {e}, retrying +{retries}");
+                    }
+                    Err(e) => {
+                        return Err(eyre::eyre!("Failed claim with {e}"));
+                    }
+                }
+            };
 
             if response.status() != StatusCode::NO_CONTENT {
                 break response;