diff --git a/group_vars/vpn.yml b/group_vars/vpn.yml
index ea2f63d..eb264d0 100644
--- a/group_vars/vpn.yml
+++ b/group_vars/vpn.yml
@@ -1,19 +1,2 @@
-headscale_version: '0.22.3'
-headscale_arch: 'amd64'
-headscale_user_name: 'headscale'
-headscale_user_group: '{{ headscale_user_name }}'
-headscale_user_uid: '800'
-headscale_user_gid: '{{ headscale_user_uid }}'
-
-headscale_binary_path: '/usr/local/bin/headscale'
-headscale_config_dir: '/etc/headscale'
-headscale_var_data_dir: '/var/lib/headscale'
-headscale_pid_dir: '/var/run/headscale'
-headscale_directories:
-  - '{{ headscale_config_dir }}'
-  - '{{ headscale_var_data_dir }}'
-  - '{{ headscale_pid_dir }}'
-
+---
 headscale_users: ['simponic']
-headscale_enable_routes: []
-headscale_exit_nodes: []
diff --git a/group_vars/webservers.yml b/group_vars/webservers.yml
new file mode 100644
index 0000000..6ac1436
--- /dev/null
+++ b/group_vars/webservers.yml
@@ -0,0 +1,2 @@
+---
+letsencrypt_email: 'elizabeth.hunt@simponic.xyz'
diff --git a/roles/vpn/tasks/main.yml b/roles/vpn/tasks/main.yml
index 4f6bcca..6ad0c57 100644
--- a/roles/vpn/tasks/main.yml
+++ b/roles/vpn/tasks/main.yml
@@ -31,6 +31,12 @@
     group: root
     mode: 0700
 
+- name: ensure headscale users
+  shell: |
+    docker exec headscale headscale user create "{{ item }}"
+  with_items:
+    - "{{ headscale_users }}"
+
 - name: daemon-reload and enable headscale
   ansible.builtin.systemd_service:
     state: restarted
diff --git a/roles/webservers/files/levi/.gitkeep b/roles/webservers/files/levi/.gitkeep
new file mode 100644
index 0000000..e69de29
diff --git a/roles/webservers/files/nginx.conf b/roles/webservers/files/nginx.conf
new file mode 100644
index 0000000..6ddd8ab
--- /dev/null
+++ b/roles/webservers/files/nginx.conf
@@ -0,0 +1,26 @@
+user www-data;
+worker_processes 4;
+pid /run/nginx.pid;
+
+events {
+  worker_connections 768;
+}
+
+http {
+  sendfile on;
+  tcp_nopush on;
+  tcp_nodelay on;
+  keepalive_timeout 65;
+  types_hash_max_size 2048;
+  include /etc/nginx/mime.types;
+  default_type application/octet-stream;
+
+  access_log /var/log/nginx/access.log;
+  error_log /var/log/nginx/error.log;
+
+  gzip on;
+  gzip_disable "msie6";
+
+  include /etc/nginx/conf.d/*.conf;
+  include /etc/nginx/sites-enabled/*;
+}
diff --git a/roles/webservers/files/nijika/headscale.simponic.xyz b/roles/webservers/files/nijika/headscale.simponic.xyz
deleted file mode 100644
index 442a2ac..0000000
--- a/roles/webservers/files/nijika/headscale.simponic.xyz
+++ /dev/null
@@ -1,48 +0,0 @@
-server {
-    server_name headscale.simponic.xyz;
-
-    location /web {
-        proxy_pass https://127.0.0.1:9443;
-        proxy_http_version 1.1;
-        proxy_set_header Upgrade $http_upgrade;
-        proxy_set_header Connection $connection_upgrade;
-        proxy_set_header Host $server_name;
-        proxy_redirect http:// https://;
-        proxy_buffering off;
-        proxy_set_header X-Real-IP $remote_addr;
-        proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
-        proxy_set_header X-Forwarded-Proto $http_x_forwarded_proto;
-        add_header Strict-Transport-Security "max-age=15552000; includeSubDomains" always;
-    }
-
-    location / {
-        proxy_pass https://127.0.0.1:27896;
-        proxy_http_version 1.1;
-        proxy_set_header Upgrade $http_upgrade;
-        proxy_set_header Connection $connection_upgrade;
-        proxy_set_header Host $server_name;
-        proxy_redirect http:// https://;
-        proxy_buffering off;
-        proxy_set_header X-Real-IP $remote_addr;
-        proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
-        proxy_set_header X-Forwarded-Proto $http_x_forwarded_proto;
-        add_header Strict-Transport-Security "max-age=15552000; includeSubDomains" always;
-    }
-
-    listen 443 ssl; # managed by Certbot
-    ssl_certificate /etc/letsencrypt/live/headscale.simponic.xyz/fullchain.pem; # managed by Certbot
-    ssl_certificate_key /etc/letsencrypt/live/headscale.simponic.xyz/privkey.pem; # managed by Certbot
-    include /etc/letsencrypt/options-ssl-nginx.conf; # managed by Certbot
-    ssl_dhparam /etc/letsencrypt/ssl-dhparams.pem; # managed by Certbot
-    keepalive_timeout 70;
-}
-
-server {
-    if ($host = headscale.simponic.xyz) {
-        return 301 https://$host$request_uri;
-    } # managed by Certbot
-
-    server_name headscale.simponic.xyz;
-    listen 80;
-    return 404; # managed by Certbot
-}
diff --git a/roles/webservers/files/nijika/http.headscale.simponic.xyz.conf b/roles/webservers/files/nijika/http.headscale.simponic.xyz.conf
new file mode 100644
index 0000000..7bfaf44
--- /dev/null
+++ b/roles/webservers/files/nijika/http.headscale.simponic.xyz.conf
@@ -0,0 +1,15 @@
+server_tokens off;
+
+server {
+  listen 80 default_server;
+  server_name headscale.simponic.xyz;
+
+  location /.well-known/acme-challenge {
+    root /var/www/letsencrypt;
+    try_files $uri $uri/ =404;
+  }
+
+  location / {
+    rewrite ^ https://headscale.simponic.xyz$request_uri? permanent;
+  }
+}
diff --git a/roles/webservers/files/nijika/https.headscale.simponic.xyz.conf b/roles/webservers/files/nijika/https.headscale.simponic.xyz.conf
new file mode 100644
index 0000000..b078672
--- /dev/null
+++ b/roles/webservers/files/nijika/https.headscale.simponic.xyz.conf
@@ -0,0 +1,46 @@
+server {
+  listen 443 ssl;
+  server_name headscale.simponic.xyz;
+
+  ssl_certificate         /etc/letsencrypt/live/headscale.simponic.xyz/fullchain.pem;
+  ssl_certificate_key     /etc/letsencrypt/live/headscale.simponic.xyz/privkey.pem;
+  ssl_trusted_certificate /etc/letsencrypt/live/headscale.simponic.xyz/fullchain.pem;
+
+  ssl_session_cache shared:SSL:50m;
+  ssl_session_timeout 5m;
+  ssl_stapling on;
+  ssl_stapling_verify on;
+
+  ssl_protocols TLSv1 TLSv1.1 TLSv1.2;
+  ssl_ciphers "ECDHE-RSA-AES256-GCM-SHA384:ECDHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM-SHA256:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES128-SHA256:ECDHE-RSA-AES256-SHA:ECDHE-RSA-AES128-SHA:DHE-RSA-AES256-SHA256:DHE-RSA-AES128-SHA256:DHE-RSA-AES256-SHA:DHE-RSA-AES128-SHA:ECDHE-RSA-DES-CBC3-SHA:EDH-RSA-DES-CBC3-SHA:AES256-GCM-SHA384:AES128-GCM-SHA256:AES256-SHA256:AES128-SHA256:AES256-SHA:AES128-SHA:DES-CBC3-SHA:HIGH:!aNULL:!eNULL:!EXPORT:!DES:!MD5:!PSK:!RC4";
+
+  ssl_dhparam /etc/nginx/dhparams.pem;
+  ssl_prefer_server_ciphers on;
+
+  location /web {
+    proxy_pass https://127.0.0.1:9443;
+    proxy_http_version 1.1;
+    proxy_set_header Upgrade $http_upgrade;
+    proxy_set_header Connection "upgrade";
+    proxy_set_header Host $server_name;
+    proxy_redirect http:// https://;
+    proxy_buffering off;
+    proxy_set_header X-Real-IP $remote_addr;
+    proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
+    proxy_set_header X-Forwarded-Proto $http_x_forwarded_proto;
+    add_header Strict-Transport-Security "max-age=15552000; includeSubDomains" always;
+  }
+
+  location / {
+    proxy_pass http://127.0.0.1:27896;
+    proxy_http_version 1.1;
+    proxy_set_header Upgrade $http_upgrade;
+    proxy_set_header Connection "upgrade";
+    proxy_set_header Host $server_name;
+    proxy_buffering off;
+    proxy_set_header X-Real-IP $remote_addr;
+    proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
+    proxy_set_header X-Forwarded-Proto $http_x_forwarded_proto;
+    add_header Strict-Transport-Security "max-age=15552000; includeSubDomains" always;
+  }
+}
diff --git a/roles/webservers/tasks/main.yml b/roles/webservers/tasks/main.yml
index 680b050..03fba22 100644
--- a/roles/webservers/tasks/main.yml
+++ b/roles/webservers/tasks/main.yml
@@ -15,4 +15,76 @@
   service: name=ufw state=restarted enabled=yes
 
 - name: install nginx
-  apt: name=nginx status=latest
+  apt: name=nginx state=latest
+
+- name: install letsencrypt
+  apt: name=letsencrypt state=latest
+
+- name: create letsencrypt directory
+  file: name=/var/www/letsencrypt state=directory
+
+- name: remove default nginx
+  file: name=/etc/nginx/sites-enabled/default state=absent
+
+- name: generate dhparams
+  shell: openssl dhparam -out /etc/nginx/dhparams.pem 2048
+  args:
+    creates: /etc/nginx/dhparams.pem
+
+- name: add system nginx config
+  template:
+    src: ../files/nginx.conf
+    dest: /etc/nginx/nginx.conf
+
+- name: copy http nginx configuration for each domain
+  copy:
+    src: "{{ item }}"
+    dest: "/etc/nginx/sites-enabled/"
+  with_fileglob:
+    - "files/{{ inventory_hostname }}/http.*.conf"
+
+- name: restart nginx to get letsencrypt certificate
+  service: name=nginx state=restarted enabled=yes
+
+- name: find deployed domains
+  ansible.builtin.find:
+    paths: "/etc/nginx/sites-enabled/"
+    patterns: "http.*.conf"
+  register: nginx_conf_files
+  delegate_to: "{{ inventory_hostname }}"
+
+- name: extract domains from deployed nginx configurations
+  shell: |
+    grep -oP 'server_name\s+\K[^;]+' "{{ item.path }}"
+  loop: "{{ nginx_conf_files.files }}"
+  register: extracted_domains
+
+- name: request letsencrypt certificate
+  shell: >
+    letsencrypt certonly -n --webroot -w /var/www/letsencrypt -m {{ letsencrypt_email }} \
+      --agree-tos -d {{ item.stdout }}
+  args:
+    creates: "/etc/letsencrypt/live/{{ item.stdout }}"
+  loop: "{{ extracted_domains.results }}"
+  when: item.stdout != ""
+
+- name: copy https nginx configuration for each domain
+  copy:
+    src: "{{ item }}"
+    dest: "/etc/nginx/sites-enabled/"
+  with_fileglob:
+    - "files/{{ inventory_hostname }}/https.*.conf"
+
+- name: reload nginx to activate sites
+  service: name=nginx state=restarted
+
+- name: add monthly letsencrypt cronjob for cert renewal based on hash of domain name to prevent hitting LE rate limits
+  cron:
+    name: "letsencrypt_renewal_{{ item.stdout }}"
+    day: "{{ '%02d' | format(1 + (item.stdout | hash('md5') | int(0, 16) % 27)) }}"
+    hour: "{{ (item.stdout | hash('md5') | int(0, 16) % 24 ) }}"
+    minute: "{{ (item.stdout | hash('md5') | int(0, 16) % 60 ) }}"
+    job: "letsencrypt renew --cert-name {{ item.stdout }} -n --webroot -w /var/www/letsencrypt -m {{ letsencrypt_email }} --agree-tos && service nginx reload"
+  loop: "{{ extracted_domains.results }}"
+  when: item.stdout != ""
+