diff --git a/.buildkite/testbot_maintenance.sh b/.buildkite/testbot_maintenance.sh
index 8b3778ad679..c77d4e7200b 100755
--- a/.buildkite/testbot_maintenance.sh
+++ b/.buildkite/testbot_maintenance.sh
@@ -18,3 +18,13 @@ if ! command -v ngrok >/dev/null; then
         ;;
     esac
 fi
+
+# Upgrade mkcert on macOS
+case $os in
+darwin)
+    brew upgrade mkcert || brew install mkcert || true
+    ;;
+windows)
+    choco upgrade -y mkcert
+    ;;
+esac
diff --git a/containers/ddev-router/Dockerfile b/containers/ddev-router/Dockerfile
index a799250fa10..3482865108f 100644
--- a/containers/ddev-router/Dockerfile
+++ b/containers/ddev-router/Dockerfile
@@ -1,6 +1,6 @@
 FROM nginx:1.17.0
 
-ENV MKCERT_VERSION=v1.3.0
+ENV MKCERT_VERSION=v1.4.0
 
 ENV DEBIAN_FRONTEND noninteractive
 ENV DOCKER_GEN_VERSION 0.7.4
diff --git a/containers/ddev-webserver/Dockerfile b/containers/ddev-webserver/Dockerfile
index d7e92261ce5..a07d8089bdd 100644
--- a/containers/ddev-webserver/Dockerfile
+++ b/containers/ddev-webserver/Dockerfile
@@ -9,7 +9,7 @@ ENV DRUSH_LAUNCHER_VERSION=0.6.0
 ENV DRUSH_LAUNCHER_FALLBACK=/usr/local/bin/drush8
 ENV MAILHOG_VERSION=1.0.0
 ENV BACKDROP_DRUSH_VERSION=1.0.0
-ENV MKCERT_VERSION=v1.3.0
+ENV MKCERT_VERSION=v1.4.0
 
 ENV DEBIAN_FRONTEND noninteractive
 ENV TERM xterm
diff --git a/pkg/version/version.go b/pkg/version/version.go
index f4597a2d003..09c915e4c53 100644
--- a/pkg/version/version.go
+++ b/pkg/version/version.go
@@ -49,7 +49,7 @@ var DockerComposeFileFormatVersion = "3.6"
 var WebImg = "drud/ddev-webserver"
 
 // WebTag defines the default web image tag for drud dev
-var WebTag = "20190819_newer_wp_cli" // Note that this can be overridden by make
+var WebTag = "20190819_update_mkcert" // Note that this can be overridden by make
 
 // DBImg defines the default db image used for applications.
 var DBImg = "drud/ddev-dbserver"
@@ -73,7 +73,7 @@ var BgsyncTag = "v1.10.0" // Note that this can be overridden by make
 var RouterImage = "drud/ddev-router"
 
 // RouterTag defines the tag used for the router.
-var RouterTag = "v1.10.0" // Note that this can be overridden by make
+var RouterTag = "20190819_update_mkcert" // Note that this can be overridden by make
 
 var SSHAuthImage = "drud/ddev-ssh-agent"