diff --git a/internal/upload/batch.go b/internal/upload/batch.go
index 89691835..cec0239b 100644
--- a/internal/upload/batch.go
+++ b/internal/upload/batch.go
@@ -226,10 +226,12 @@ func (uploadBatch *uploadBatch) initUpload() ([]string, error) {
 		return files, nil
 	}
 
+	var entryFile string
+	var err error
 	for len(files) > 0 {
-		entryFile := files[0]
+		entryFile = files[0]
 		files = files[1:]
-		err := uploadBatch.uploadFile(entryFile)
+		err = uploadBatch.uploadFile(entryFile)
 		if err == nil {
 			printSuccessfulUpload(entryFile)
 
@@ -237,7 +239,9 @@ func (uploadBatch *uploadBatch) initUpload() ([]string, error) {
 		}
 	}
 
-	return files, errors.New("failed to initialize a scan due to badly formatted files")
+	errStr := fmt.Sprintf("failed to initialize a scan due to badly formatted files, initial upload file %s got the following error: %s", entryFile, err.Error())
+
+	return files, errors.New(errStr)
 }
 
 type uploadedFile struct {
diff --git a/internal/upload/batch_test.go b/internal/upload/batch_test.go
index 4f9c446a..ba9c9bdb 100644
--- a/internal/upload/batch_test.go
+++ b/internal/upload/batch_test.go
@@ -102,6 +102,8 @@ func TestInitUploadBadFile(t *testing.T) {
 
 	assert.Empty(t, files)
 	assert.ErrorContains(t, err, "failed to initialize a scan due to badly formatted files")
+	assert.ErrorContains(t, err, "testdata/misc/requirements.txt")
+	assert.ErrorContains(t, err, "tried to upload empty file")
 }
 
 func TestInitUpload(t *testing.T) {