diff --git a/apps/studio/state/storage-explorer.tsx b/apps/studio/state/storage-explorer.tsx
index 85e4eb938e7..4e98579275d 100644
--- a/apps/studio/state/storage-explorer.tsx
+++ b/apps/studio/state/storage-explorer.tsx
@@ -1215,7 +1215,7 @@ function createStorageExplorerState({
                   const status = error.originalResponse?.getStatus()
 
                   switch (status) {
-                    case 415:
+                    case 415: {
                       // Unsupported mime type
                       toast.error(
                         capitalize(
@@ -1227,20 +1227,38 @@ function createStorageExplorerState({
                         }
                       )
                       break
-                    case 413:
+                    }
+                    case 413: {
                       // Payload too large
                       toast.error(
                         `Failed to upload ${file.name}: File size exceeds the bucket file size limit.`
                       )
                       break
-                    case 409:
+                    }
+                    case 409: {
                       // Resource already exists
                       toast.error(`Failed to upload ${file.name}: File name already exists.`)
                       break
-                    case 400:
-                      // Invalid key
-                      toast.error(`Failed to upload ${file.name}: File name is invalid`)
+                    }
+                    case 400: {
+                      const responseBody = error.originalResponse?.getBody()
+                      if (typeof responseBody === 'string') {
+                        if (responseBody.includes('Invalid key:')) {
+                          toast.error(`Failed to upload ${file.name}: File name is invalid.`)
+                          break
+                        }
+
+                        if (responseBody.includes('Invalid Compact JWS')) {
+                          toast.error(`Failed to upload ${file.name}: Invalid Compact JWS.`)
+                          break
+                        }
+                      }
+                      // if it's not handled by the two ifs, fallthrough to the default case which shows the generic error message
+                    }
+                    default: {
+                      toast.error(`Failed to upload ${file.name}: ${error.message}`)
                       break
+                    }
                   }
                 } else {
                   toast.error(`Failed to upload ${file.name}: ${error.message}`)