diff --git a/tubesync/upgrade_yt-dlp.sh b/tubesync/upgrade_yt-dlp.sh
new file mode 100755
index 00000000..9da6d555
--- /dev/null
+++ b/tubesync/upgrade_yt-dlp.sh
@@ -0,0 +1,38 @@
+#!/usr/bin/env bash
+
+warning_message() {
+    cat <<EOM
+Please report any issues that you have encountered before updating yt-dlp.
+
+This is a tool to assist developers with debugging YouTube issues.
+It should not be used as an alternative to updating container images!
+EOM
+} 1>&2
+
+pip3() {
+    local pip_runner pip_whl run_whl
+
+    # pipenv
+    pip_runner='/usr/lib/python3/dist-packages/pipenv/patched/pip/__pip-runner__.py'
+    test -s "${pip_runner}" || pip_runner=''
+
+    # python3-pip-whl
+    pip_whl="$(ls -1r /usr/share/python-wheels/pip-*-py3-none-any.whl | head -n 1)"
+    run_whl="${pip_whl}/pip"
+
+    python3 "${pip_runner:-"${run_whl}"}" "$@"
+}
+
+warning_message
+test -n "${TUBESYNC_DEBUG}" || exit 1
+
+# Use the flag added in 23.0.1, if possible.
+# https://github.com/pypa/pip/pull/11780
+break_system_packages='--break-system-packages'
+pip_version="$(pip3 --version | awk '$1 = "pip" { print $2; exit; }')"
+if [[ "${pip_version}" < "23.0.1" ]]; then
+    break_system_packages=''
+fi
+
+pip3 install --upgrade ${break_system_packages} yt-dlp
+