diff --git a/Dockerfile b/Dockerfile
index 95c8249..48c9dcb 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -25,7 +25,7 @@ WORKDIR /app
 EXPOSE 8080
 
 HEALTHCHECK --interval=1m --timeout=20s --retries=3 \
-  CMD wget --no-verbose --tries=1 --spider http://localhost:${LISTEN_PORT:-8080}${BASE_URL:-/}healthcheck || exit 1
+  CMD wget --no-verbose --tries=1 --spider http://localhost:${LISTEN_PORT:-8080}/${BASE_URL}/healthcheck || exit 1
 
 CMD [ "node", "index.js" ]
 
diff --git a/server/src/middleware/app/webroot.js b/server/src/middleware/app/webroot.js
index dfccc0b..a8a0acb 100644
--- a/server/src/middleware/app/webroot.js
+++ b/server/src/middleware/app/webroot.js
@@ -10,10 +10,9 @@ console.info(`Using web root: ${trimedWebRoot}`);
 
 module.exports = function (app) {
   if (trimedWebRoot !== '') {
-
     // Prevent access to any URL not starting with the configured BASE_URL
     app.use(function (req, res, next) {
-      if (!req.path.startsWith(`${trimedWebRoot}`)) {
+      if (!req.path.replace(new RegExp('^/+'), '/').startsWith(`${trimedWebRoot}`)) {
         console.error('[400]', 'Invalid incoming request URL:', `${req.method} ${req.path}`);
         res.status(400)
           .json({
@@ -28,7 +27,7 @@ module.exports = function (app) {
     });
 
     // Load express-urlrewrite
-    app.use(rewrite(new RegExp(`^/?${trimedWebRoot}+(.*)`), '/$1'));
+    app.use(rewrite(new RegExp(`^/*${trimedWebRoot}+(.*)`), '/$1'));
 
     // Override response.redirect() to preprend BASE_URL
     app.use(function (req, res, next) {