diff --git a/tests/mixins/test_browsing.py b/tests/mixins/test_browsing.py
index f60f20fc..0c530a14 100644
--- a/tests/mixins/test_browsing.py
+++ b/tests/mixins/test_browsing.py
@@ -4,7 +4,8 @@
 from unittest import mock
 
 import pytest
-from test_helpers import is_ci
+
+from tests.test_helpers import is_ci
 
 
 class TestBrowsing:
diff --git a/tests/mixins/test_uploads.py b/tests/mixins/test_uploads.py
index a3856564..9e1d6ca5 100644
--- a/tests/mixins/test_uploads.py
+++ b/tests/mixins/test_uploads.py
@@ -1,10 +1,12 @@
 import tempfile
 import time
+from unittest import mock
 
 import pytest
 
 from tests.conftest import get_resource
 from ytmusicapi.enums import ResponseStatus
+from ytmusicapi.exceptions import YTMusicUserError
 from ytmusicapi.ytmusic import YTMusic
 
 
@@ -51,6 +53,12 @@ def test_upload_song(self, config, yt_auth):
         response = yt_auth.upload_song(get_resource(config["uploads"]["file"]))
         assert response.status_code == 409
 
+        with (
+            mock.patch("os.path.getsize", return_value=4 * 10**9),
+            pytest.raises(YTMusicUserError, match="larger than the limit of 300MB"),
+        ):
+            yt_auth.upload_song(get_resource(config["uploads"]["file"]))
+
     def test_upload_song_and_verify(self, config, yt_auth: YTMusic):
         """Upload a song and verify it can be retrieved after it finishes processing."""
         upload_response = yt_auth.upload_song(get_resource(config["uploads"]["file"]))
diff --git a/ytmusicapi/mixins/uploads.py b/ytmusicapi/mixins/uploads.py
index 7bb91f3b..2ccdbfd5 100644
--- a/ytmusicapi/mixins/uploads.py
+++ b/ytmusicapi/mixins/uploads.py
@@ -225,6 +225,10 @@ def upload_song(self, filepath: str) -> Union[ResponseStatus, requests.Response]
         headers = self.headers.copy()
         upload_url = f"https://upload.youtube.com/upload/usermusic/http?authuser={headers['x-goog-authuser']}"
         filesize = os.path.getsize(filepath)
+        if filesize >= 314572800:  # 300MB in bytes
+            msg = f"File {filepath} has size {filesize} bytes, which is larger than the limit of 300MB"
+            raise YTMusicUserError(msg)
+
         body = ("filename=" + ntpath.basename(filepath)).encode("utf-8")
         headers.pop("content-encoding", None)
         headers["content-type"] = "application/x-www-form-urlencoded;charset=utf-8"