diff --git a/photon-server/src/main/java/org/photonvision/server/RequestHandler.java b/photon-server/src/main/java/org/photonvision/server/RequestHandler.java
index 69726c9adb..9547c2cdf0 100644
--- a/photon-server/src/main/java/org/photonvision/server/RequestHandler.java
+++ b/photon-server/src/main/java/org/photonvision/server/RequestHandler.java
@@ -537,9 +537,12 @@ private static Optional<File> handleTempFileCreation(UploadedFile file) {
                 new File(Path.of(System.getProperty("java.io.tmpdir"), file.filename()).toString());
         boolean makeDirsRes = tempFilePath.getParentFile().mkdirs();
 
-        if (!makeDirsRes) {
+        if (!makeDirsRes && !(tempFilePath.getParentFile().exists())) {
             logger.error(
-                    "There was an error while uploading " + file.filename() + " to the temp folder!");
+                    "There was an error while creating "
+                            + tempFilePath.getAbsolutePath()
+                            + "! Exists: "
+                            + tempFilePath.getParentFile().exists());
             return Optional.empty();
         }
 
@@ -547,7 +550,10 @@ private static Optional<File> handleTempFileCreation(UploadedFile file) {
             FileUtils.copyInputStreamToFile(file.content(), tempFilePath);
         } catch (IOException e) {
             logger.error(
-                    "There was an error while uploading " + file.filename() + " to the temp folder!");
+                    "There was an error while copying "
+                            + file.filename()
+                            + " to the temp file "
+                            + tempFilePath.getAbsolutePath());
             return Optional.empty();
         }