diff --git a/automated install/basic-install.sh b/automated install/basic-install.sh
index 61d759ff..8380ca49 100755
--- a/automated install/basic-install.sh	
+++ b/automated install/basic-install.sh	
@@ -2004,8 +2004,15 @@ main() {
       # just install the Core dependencies
       DEPS=("${PIHOLE_DEPS[@]}")
     fi
+
     install_dependent_packages DEPS[@]
 
+    # On some systems, lighttpd is not enabled on first install. We need to enable it here if the user
+    # has chosen to install the web interface, else the `LIGHTTPD_ENABLED` check will fail
+    if [[ "${INSTALL_WEB}" == true ]]; then
+      enable_service lighttpd
+    fi
+
     if [[ -x "$(command -v systemctl)" ]]; then
       # Value will either be 1, if true, or 0
       LIGHTTPD_ENABLED=$(systemctl is-enabled lighttpd | grep -c 'enabled' || true)