diff --git a/src/components/MediaSettingsModal/MediaSettingsSchema.jsx b/src/components/MediaSettingsModal/MediaSettingsSchema.jsx
index f89b85d99..26f6fbae1 100644
--- a/src/components/MediaSettingsModal/MediaSettingsSchema.jsx
+++ b/src/components/MediaSettingsModal/MediaSettingsSchema.jsx
@@ -27,6 +27,13 @@ export const MediaSettingsSchema = (existingTitlesArray = []) =>
           return (value.match(/\./g) || []).length <= 1
         }
       )
+      .test(
+        "File not supported",
+        "File names must begin with a letter or number",
+        (value) => {
+          return /^[a-zA-Z0-9]/.test(value)
+        }
+      )
       .min(
         MEDIA_SETTINGS_TITLE_MIN_LENGTH,
         `Title must be longer than ${MEDIA_SETTINGS_TITLE_MIN_LENGTH} characters`
diff --git a/src/hooks/mediaHooks/useCreateMultipleMedia.ts b/src/hooks/mediaHooks/useCreateMultipleMedia.ts
index 58f71e697..fe10cf6e2 100644
--- a/src/hooks/mediaHooks/useCreateMultipleMedia.ts
+++ b/src/hooks/mediaHooks/useCreateMultipleMedia.ts
@@ -48,6 +48,8 @@ export const useCreateMultipleMedia = (
           // with a safe replacement character
           newFileName: `${getFileName(file.name)
             .replaceAll(/[\W\s]/g, "_")
+            // Remove any leading underscores
+            .replace(/^_+/g, "")
             .trim()}.${getFileExt(file.name)}`,
         }))
       )