diff --git a/plugins/nginx-vhosts/functions b/plugins/nginx-vhosts/functions
index 2add2e4f0..1964b45b9 100755
--- a/plugins/nginx-vhosts/functions
+++ b/plugins/nginx-vhosts/functions
@@ -69,6 +69,7 @@ configure_nginx_ports() {
   local DOKKU_NGINX_SSL_PORT=$(config_get "$APP" DOKKU_NGINX_SSL_PORT)
   local DOKKU_PROXY_PORT_MAP=$(config_get "$APP" DOKKU_PROXY_PORT_MAP)
   local IS_APP_VHOST_ENABLED="$(is_app_vhost_enabled "$APP")"
+  local UPSTREAM_PORT="5000"
 
   if [[ -z "$DOKKU_NGINX_PORT" ]] && [[ -z "$RAW_TCP_PORTS" ]]; then
     if [[ "$IS_APP_VHOST_ENABLED" == "false" ]]; then
@@ -77,8 +78,8 @@ configure_nginx_ports() {
     else
       local NGINX_PORT=80
     fi
+    config_set --no-restart "$APP" DOKKU_NGINX_PORT="$NGINX_PORT"
   fi
-
   if [[ -z "$DOKKU_NGINX_SSL_PORT" ]]; then
     if (is_ssl_enabled "$APP") && [[ -z "$RAW_TCP_PORTS" ]]; then
       if [[ "$IS_APP_VHOST_ENABLED" == "false" ]]; then
@@ -88,8 +89,8 @@ configure_nginx_ports() {
         local NGINX_SSL_PORT=443
       fi
     fi
+    config_set --no-restart "$APP" DOKKU_NGINX_SSL_PORT="$NGINX_SSL_PORT"
   fi
-
   if [[ -z "$DOKKU_PROXY_PORT_MAP" ]]; then
     if [[ -n "$RAW_TCP_PORTS" ]]; then
       local RAW_TCP_PORT
@@ -99,14 +100,13 @@ configure_nginx_ports() {
     else
       local NGINX_PORT=${NGINX_PORT:-$DOKKU_NGINX_PORT}
       local NGINX_SSL_PORT=${NGINX_SSL_PORT:-$DOKKU_NGINX_SSL_PORT}
-
+      [[ -f "$DOKKU_ROOT/$APP/PORT.web.1" ]] && local UPSTREAM_PORT="$(< "$DOKKU_ROOT/$APP/PORT.web.1")"
       if [[ -n "$NGINX_PORT" ]] && [[ -n "$NGINX_SSL_PORT" ]]; then
-        local PROXY_PORT_MAP+=" http:${NGINX_PORT}:5000 https:${NGINX_SSL_PORT}:5000 "
+        local PROXY_PORT_MAP+=" http:${NGINX_PORT}:$UPSTREAM_PORT https:${NGINX_SSL_PORT}:$UPSTREAM_PORT "
       elif [[ -n "$NGINX_PORT" ]]; then
-        local PROXY_PORT_MAP+=" http:${NGINX_PORT}:5000 "
+        local PROXY_PORT_MAP+=" http:${NGINX_PORT}:$UPSTREAM_PORT "
       fi
     fi
-
     if [[ -n "$PROXY_PORT_MAP" ]]; then
       local PROXY_PORT_MAP="$(echo "$PROXY_PORT_MAP" | xargs)"
       local PROXY_PORT_MAP+=" $(merge_dedupe_list "$(remove_val_from_list "$PORT_MAP" "$DOKKU_PROXY_PORT_MAP" " ")" " ") "
diff --git a/plugins/nginx-vhosts/templates/nginx.conf.sigil b/plugins/nginx-vhosts/templates/nginx.conf.sigil
index 931604bbe..6ac5d721b 100644
--- a/plugins/nginx-vhosts/templates/nginx.conf.sigil
+++ b/plugins/nginx-vhosts/templates/nginx.conf.sigil
@@ -11,8 +11,7 @@ server {
   {{ if $.NOSSL_SERVER_NAME }}server_name {{ $.NOSSL_SERVER_NAME }}; {{ end }}
   access_log  /var/log/nginx/{{ $.APP }}-access.log;
   error_log   /var/log/nginx/{{ $.APP }}-error.log;
-{{ if $.SSL_INUSE }}
-{{ if eq $listen_port "80" }}
+{{ if (and (eq $listen_port "80") ($.SSL_INUSE)) }}
   return 301 https://$host:{{ $.NGINX_SSL_PORT }}$request_uri;
 {{ else }}
   location    / {
@@ -35,7 +34,7 @@ server {
     proxy_set_header X-Request-Start $msec;
   }
   include {{ $.DOKKU_ROOT }}/{{ $.APP }}/nginx.conf.d/*.conf;
-{{ end }}{{ end }}
+{{ end }}
 }
 {{ else if eq $scheme "https"}}
 server {
diff --git a/tests/unit/40_core_2.bats b/tests/unit/40_core_2.bats
index e8cc44671..b3d860243 100644
--- a/tests/unit/40_core_2.bats
+++ b/tests/unit/40_core_2.bats
@@ -57,20 +57,20 @@ build_nginx_config() {
   setup_test_tls
   assert_urls "https://dokku.me"
   build_nginx_config
-  assert_urls "https://${TEST_APP}.dokku.me"
+  assert_urls "http://${TEST_APP}.dokku.me" "https://${TEST_APP}.dokku.me"
   add_domain "test.dokku.me"
-  assert_urls "https://test.dokku.me" "https://${TEST_APP}.dokku.me"
+  assert_urls "http://test.dokku.me" "http://${TEST_APP}.dokku.me" "https://test.dokku.me" "https://${TEST_APP}.dokku.me"
 }
 
 @test "(core) urls (wildcard ssl)" {
   setup_test_tls wildcard
   assert_urls "https://dokku.me"
   build_nginx_config
-  assert_urls "https://${TEST_APP}.dokku.me"
+  assert_urls "http://${TEST_APP}.dokku.me" "https://${TEST_APP}.dokku.me"
   add_domain "test.dokku.me"
-  assert_urls "https://test.dokku.me" "https://${TEST_APP}.dokku.me"
+  assert_urls "http://test.dokku.me" "http://${TEST_APP}.dokku.me" "https://test.dokku.me" "https://${TEST_APP}.dokku.me"
   add_domain "dokku.example.com"
-  assert_urls "https://dokku.example.com" "https://test.dokku.me" "https://${TEST_APP}.dokku.me"
+  assert_urls "http://dokku.example.com" "http://test.dokku.me" "http://${TEST_APP}.dokku.me" "https://dokku.example.com" "https://test.dokku.me" "https://${TEST_APP}.dokku.me"
 }
 
 @test "(core) git-remote (off-port)" {