diff --git a/mod-fabric/resources/assets/pixelchat/lang/en_us.json b/mod-fabric/resources/assets/pixelchat/lang/en_us.json
index aa69a57..d36334a 100644
--- a/mod-fabric/resources/assets/pixelchat/lang/en_us.json
+++ b/mod-fabric/resources/assets/pixelchat/lang/en_us.json
@@ -1,5 +1,6 @@
 {
   "pixelchat.uploading": "Uploading",
-  "pixelchat.upload_failed": "Upload failed",
+  "pixelchat.upload_failed.no_error": "Upload failed",
+  "pixelchat.upload_failed.error": "Upload failed - %s",
   "pixelchat.upload_completed": "Upload completed"
 }
\ No newline at end of file
diff --git a/mod-fabric/src/eu/e99/pixelchat/fabric/image/ImageUploads.java b/mod-fabric/src/eu/e99/pixelchat/fabric/image/ImageUploads.java
index 98eb7c5..63ece30 100644
--- a/mod-fabric/src/eu/e99/pixelchat/fabric/image/ImageUploads.java
+++ b/mod-fabric/src/eu/e99/pixelchat/fabric/image/ImageUploads.java
@@ -46,21 +46,32 @@ public class ImageUploads {
         this.minecraft.send(() -> bossBars.add(bossBar.getUuid(), bossBar));
 
         String url = null;
+        Throwable error = null;
+
         for (String host : this.hosts) {
             try {
                 url = this.upload(host, path);
+                error = null;
                 break;
             } catch (Throwable e) {
+                error = e;
                 PixelChat.LOGGER.warn("Failed to upload", e);
             }
         }
 
         // IntelliJ complains otherwise
         String finalUrl = url;
+        Throwable finalError = error;
+
         this.minecraft.send(() -> {
             if (finalUrl == null) {
                 PixelChat.LOGGER.error("No uploader succeeded");
-                bossBar.setName(Text.translatable("pixelchat.upload_failed"));
+
+                Text message = finalError == null ?
+                        Text.translatable("pixelchat.upload_failed.no_error") :
+                        Text.translatable("pixelchat.upload_failed.error", finalError.getMessage());
+
+                bossBar.setName(message);
                 bossBar.setPercent(1.0f);
                 bossBar.setColor(BossBar.Color.RED);
                 return;
@@ -100,7 +111,7 @@ public class ImageUploads {
         );
         if (res.statusCode() != 201) {
             String body = res.body();
-            throw new RuntimeException(String.format("Failed to upload, expected status 201, got %d, body: %s", res.statusCode(), body));
+            throw new RuntimeException(String.format("%d: %s", res.statusCode(), body));
         }
 
         String id = res.body();
diff --git a/server/src/eu/e99/pixelchat/server/ImageHandler.java b/server/src/eu/e99/pixelchat/server/ImageHandler.java
index d8a6891..546d695 100644
--- a/server/src/eu/e99/pixelchat/server/ImageHandler.java
+++ b/server/src/eu/e99/pixelchat/server/ImageHandler.java
@@ -6,10 +6,10 @@ import io.javalin.http.Context;
 import io.javalin.http.HttpStatus;
 import org.apache.commons.imaging.ImageFormats;
 import org.apache.commons.imaging.Imaging;
+import org.apache.commons.imaging.ImagingException;
 import org.slf4j.Logger;
 
 import java.awt.image.BufferedImage;
-import java.io.IOException;
 import java.io.InputStream;
 import java.time.Instant;
 import java.time.temporal.TemporalAmount;
@@ -51,22 +51,22 @@ public class ImageHandler {
                     status(HttpStatus.CREATED).
                     contentType(ContentType.TEXT_PLAIN).
                     result(id);
-        } catch (IllegalArgumentException ignored) {
+        } catch (ImagingException | IllegalArgumentException ignored) {
             ctx
                     .status(HttpStatus.BAD_REQUEST)
                     .result("Unrecognized image format");
-        } catch (IOException e) {
-            ctx
-                    .status(HttpStatus.INTERNAL_SERVER_ERROR)
-                    .result("Internal Server Error");
-
-            this.logger.error("Failed to upload image", e);
         } catch (OutOfMemoryError e) {
             ctx
                     .status(HttpStatus.INSUFFICIENT_STORAGE)
                     .result("Insufficient storage on server");
 
             this.logger.error("Out of memory", e);
+        } catch (Throwable e) {
+            ctx
+                    .status(HttpStatus.INTERNAL_SERVER_ERROR)
+                    .result("Internal Server Error");
+
+            this.logger.error("Failed to upload image", e);
         }
     }
 
@@ -86,7 +86,7 @@ public class ImageHandler {
                     status(HttpStatus.OK).
                     contentType(ContentType.IMAGE_PNG).
                     result(png);
-        } catch (IOException e) {
+        } catch (Throwable e) {
             ctx
                     .status(HttpStatus.INTERNAL_SERVER_ERROR)
                     .result("Internal Server Error");