diff --git a/scripts/enter.sh b/scripts/enter.sh
index cc6c619c2..71791c8a8 100755
--- a/scripts/enter.sh
+++ b/scripts/enter.sh
@@ -6,6 +6,10 @@ CACHE_DIR="${CACHE_DIR:-$HOME/hassos-cache}"
 sudo mkdir -p "${CACHE_DIR}"
 sudo chown -R "${BUILDER_UID}:${BUILDER_GID}" "${CACHE_DIR}"
 sudo docker build -t hassos:local .
+
+# Make sure loop devices are present before starting the container
+sudo losetup -f > /dev/null
+
 sudo docker run -it --rm --privileged \
   -v "$(pwd):/build" -v "${CACHE_DIR}:/cache" \
   -e BUILDER_UID="${BUILDER_UID}" -e BUILDER_GID="${BUILDER_GID}" \