diff --git a/start b/start
index 2214092..fa09f82 100755
--- a/start
+++ b/start
@@ -10,6 +10,18 @@ if ! test -f "$SCRIPT_DIR/.undercover_init_successful"; then
     fi
 fi
 
+function may-init {
+    if $@; then
+        return 0
+    else
+        echo "Service start failed. Re-initializing."
+        rm "$SCRIPT_DIR/.undercover_init_successful"
+        "$SCRIPT_DIR/init"
+        source "$SCRIPT_DIR/.venv/bin/activate"
+        $@
+    fi
+}
+
 if ! pip3 -V | grep -E "$SCRIPT_DIR/\.?venv"; then
     echo "Entering virtual environment..."
     source "$SCRIPT_DIR/.venv/bin/activate"
@@ -23,9 +35,9 @@ fi
 
 if [[ "$1" == "prod" ]]; then
     echo "Starting gunicorn production server..."
-    gunicorn -b "localhost:$PROD_PORT" "app:create_app()"
+    may-init gunicorn -b "localhost:$PROD_PORT" "app:create_app()"
 else
     echo "Starting local dev server..."
     export FLASK_APP=app
-    flask --debug run --host=0.0.0.0
+    may-init flask --debug run --host=0.0.0.0
 fi