diff --git a/files/cli.py b/files/cli.py
index b16c34d98..6f5f7c38f 100644
--- a/files/cli.py
+++ b/files/cli.py
@@ -2,6 +2,13 @@ from .__main__ import app, db_session, cache
 from flask import g
 import files.helpers.cron
 
+import os
+from pathlib import Path
+
+# cli.py runs in <repo-root>/files, whereas our relative paths assume
+# the WD is <repo-root>. NOTE: Change this if cli.py is ever moved.
+os.chdir(Path(__file__).parent.parent)
+
 #from flask_migrate import Migrate
 #from flask_sqlalchemy import SQLAlchemy
 #import files.classes