diff --git a/resources/docker/entrypoint.sh b/resources/docker/entrypoint.sh
index 5b74fa4e..b90042a0 100644
--- a/resources/docker/entrypoint.sh
+++ b/resources/docker/entrypoint.sh
@@ -6,8 +6,21 @@ shift
 
 # If the configuration file does not exist wait until it does.
 
+loop_count=0
 while [ ! -f "${CONFIG}" ] || grep -q "__CERT_PATH__" /opt/stalwart-mail/etc/common/tls.toml; do
     sleep 1
+    if [ $(($loop_count % 30)) -eq 0 ]; then
+        if [ ! -f "${CONFIG}" ]; then
+            echo "ERROR: Configuration file ${CONFIG} not found."
+            echo "Please execute 'docker exec -it $HOSTNAME stalwart-install' to fix and start service"
+        fi
+        if grep -q "__CERT_PATH__" /opt/stalwart-mail/etc/common/tls.toml; then
+            echo "ERROR: TLS not configured."
+            echo "Please check etc/common/tls.toml file in your configuration volume"
+        fi
+        echo "ERROR: Service will wait for configuration to be fixed before startup"
+    fi
+    loop_count=$(($loop_count+1))
 done
 
 # If the configuration file exists, start the server.