diff --git a/playbooks/group_vars/db.yml b/playbooks/group_vars/db.yml
index 374377a1..8fa48d6b 100644
--- a/playbooks/group_vars/db.yml
+++ b/playbooks/group_vars/db.yml
@@ -37,6 +37,7 @@ postgresql_ssl_certificate:
   csr_common_name: "{{ db_server.host }}"
   certificate_filename: "{{ postgresql.base_directory }}/certs/server.crt"
   provider: selfsigned
+  selfsigned_not_after: +3650d
   cache_filename: "{{ database_server_certificate_cache_filename }}" # where to store the server certificate in cache
 
 firewalld_rich_rules:
diff --git a/playbooks/group_vars/omero.yml b/playbooks/group_vars/omero.yml
index 8c784c45..6b533d21 100644
--- a/playbooks/group_vars/omero.yml
+++ b/playbooks/group_vars/omero.yml
@@ -14,6 +14,7 @@ postgresql_client_ssl_certificate:
   csr_common_name: "{{ web_server.host }}"
   certificate_filename: /opt/omero/server/.postgresql/postgresql.crt
   provider: selfsigned
+  selfsigned_not_after: +3650d
   cache_filename: "{{ database_client_certificate_cache_filename }}" # where to store the client certificate in cache
 
 # firewalld
diff --git a/playbooks/group_vars/xnat.yml b/playbooks/group_vars/xnat.yml
index eb35a9fe..8ecca5b5 100644
--- a/playbooks/group_vars/xnat.yml
+++ b/playbooks/group_vars/xnat.yml
@@ -21,7 +21,7 @@ xnat_source:
   context_file_location: /usr/share/tomcat/webapps/ROOT/META-INF/context.xml
 
 # mirsg.infrastructure.tomcat
-tomcat_version: 9.0.82
+tomcat_version: 9.0.97
 tomcat_owner: tomcat
 tomcat_group: tomcat
 
@@ -60,6 +60,7 @@ postgresql_client_ssl_certificate:
   csr_common_name: "{{ web_server.host }}"
   certificate_filename: /usr/share/tomcat/.postgresql/postgresql.crt
   provider: selfsigned
+  selfsigned_not_after: +3650d
   cache_filename: "{{ database_client_certificate_cache_filename }}" # where to store the client certificate in cache
 
 java:
diff --git a/playbooks/molecule/resources/monitoring/inventory/host_vars/mserv.yml b/playbooks/molecule/resources/monitoring/inventory/host_vars/mserv.yml
index 3b7a6549..986a87f4 100644
--- a/playbooks/molecule/resources/monitoring/inventory/host_vars/mserv.yml
+++ b/playbooks/molecule/resources/monitoring/inventory/host_vars/mserv.yml
@@ -9,3 +9,4 @@ monitoring_server_ssl_certificate:
   csr_common_name: "{{ hostvars['mserv']['hostname'] }}"
   certificate_filename: /etc/ssl/certs/{{ hostvars['mserv']['hostname'] }}.cert
   provider: selfsigned
+  selfsigned_not_after: +3650d
diff --git a/roles/nginx/README.md b/roles/nginx/README.md
index 8f38247c..0f881619 100644
--- a/roles/nginx/README.md
+++ b/roles/nginx/README.md
@@ -32,8 +32,8 @@ variables:
 | ------------------------------- | ----------------------------------------------------------------------------------------- |
 | `nginx_use_ssl`                 | Whether to use SSL. Defaults to `true`                                                    |
 | `nginx_certs_dir`               | Where to store the certificates. Defaults to `/etc/nginx/ssl`                             |
-| `nginx_server_cert_cache`       | Path to SSL certificate on the Ansible Controller. Required if using SSL; no default      |
-| `nginx_server_key_cache`        | Path to SSL certificate on the Ansible Controller. Required if using SSL; no default      |
+| `nginx_server_cert_cache`       | Path to SSL certificates on the Ansible host. Required if using SSL; no default           |
+| `nginx_server_key_cache`        | Path to SSL certificate on the Ansible host. Required if using SSL; no default            |
 | `nginx_ssl_cert_file`           | Path to copy the SSL certificate to. Defaults to `/etc/nginx/ssl/server.cert`             |
 | `nginx_ssl_key_file`            | Path to copy the SSL key to. Defaults to `/etc/nginx/ssl/server.key`                      |
 | `nginx_diffie_helman_size_bits` | Bit size for OpenSSL Diffie-Hellman Parameters. Defaults to `4096`                        |
diff --git a/roles/nginx/molecule/centos7/molecule.yml b/roles/nginx/molecule/centos7/molecule.yml
index 0279dcbd..15b4ec4b 100644
--- a/roles/nginx/molecule/centos7/molecule.yml
+++ b/roles/nginx/molecule/centos7/molecule.yml
@@ -30,6 +30,6 @@ platforms:
       - 443
       - 8000
     published_ports:
-      - 127.0.0.1:8080:80
+      - 127.0.0.1:8080:443
     etc_hosts:
       molecule.instance.local: 192.168.56.2
diff --git a/roles/nginx/molecule/resources/inventory/group_vars/all.yml b/roles/nginx/molecule/resources/inventory/group_vars/all.yml
index 018954e3..a2343cf5 100644
--- a/roles/nginx/molecule/resources/inventory/group_vars/all.yml
+++ b/roles/nginx/molecule/resources/inventory/group_vars/all.yml
@@ -1,6 +1,39 @@
 ---
+nginx_owner: root
+nginx_group: root
+
 nginx_server_name: molecule.instance.local
 nginx_proxy_port: 8000
 nginx_diffie_helman_size_bits: 2048
 nginx_root: /home/
-nginx_use_ssl: false
+
+nginx_use_ssl: true
+nginx_certs_dir: /etc/nginx/ssl
+nginx_ssl_cert_file: /etc/nginx/ssl/server.cert
+nginx_ssl_key_file: /etc/nginx/ssl/server.key
+nginx_server_cert_cache: /etc/ssl/certs/server.cert
+nginx_server_key_cache: /etc//ssl/certs/server.key
+
+nginx_old_ssl_certificate:
+  owner: "{{ nginx_owner }}"
+  group: "{{ nginx_group }}"
+  certificate_directory: /etc/ssl/certs
+  privatekey_filename: "{{ nginx_server_key_cache }}"
+  use_pk8: false
+  csr_filename: /etc/ssl/certs/server.csr"
+  csr_common_name: "{{ nginx_server_name }}"
+  certificate_filename: "{{ nginx_server_cert_cache }}"
+  provider: selfsigned
+  selfsigned_not_after: +365d
+
+nginx_new_ssl_certificate:
+  owner: "{{ nginx_owner }}"
+  group: "{{ nginx_group }}"
+  certificate_directory: "{{ nginx_certs_dir }}"
+  privatekey_filename: "{{ nginx_ssl_key_file }}"
+  use_pk8: false
+  csr_filename: "{{ nginx_certs_dir }}/server.csr"
+  csr_common_name: "{{ nginx_server_name }}"
+  certificate_filename: "{{ nginx_ssl_cert_file }}"
+  provider: selfsigned
+  selfsigned_not_after: +3650d
diff --git a/roles/nginx/molecule/resources/inventory/group_vars/centos7.yml b/roles/nginx/molecule/resources/inventory/group_vars/centos7.yml
index 8be670cc..aff12e5b 100644
--- a/roles/nginx/molecule/resources/inventory/group_vars/centos7.yml
+++ b/roles/nginx/molecule/resources/inventory/group_vars/centos7.yml
@@ -11,6 +11,7 @@ install_python:
     - libselinux-python
     - policycoreutils-python
   pip_packages:
+    - cryptography
     - gunicorn
     - Flask
 
diff --git a/roles/nginx/molecule/resources/inventory/group_vars/rocky9.yml b/roles/nginx/molecule/resources/inventory/group_vars/rocky9.yml
index e587b569..044f6ca3 100644
--- a/roles/nginx/molecule/resources/inventory/group_vars/rocky9.yml
+++ b/roles/nginx/molecule/resources/inventory/group_vars/rocky9.yml
@@ -11,6 +11,7 @@ install_python:
     - python3-libselinux
     - policycoreutils-python-utils
   pip_packages:
+    - cryptography
     - gunicorn
     - flask
 
diff --git a/roles/nginx/molecule/resources/prepare.yml b/roles/nginx/molecule/resources/prepare.yml
index 3c014205..b0542b2e 100644
--- a/roles/nginx/molecule/resources/prepare.yml
+++ b/roles/nginx/molecule/resources/prepare.yml
@@ -44,3 +44,21 @@
       ansible.builtin.systemd:
         name: gunicorn
         state: restarted
+
+- name: Create SSL certificates for nginx
+  hosts: all
+  gather_facts: true
+  tasks:
+    - name:
+        Create SSL certificate that expires in 1 year and store in server cache
+      ansible.builtin.include_role:
+        name: mirsg.infrastructure.ssl_certificates
+      vars:
+        ssl_certificate: "{{ nginx_old_ssl_certificate }}" # noqa: var-naming[no-role-prefix]
+    - name:
+        Create SSL certificate that expires in 10 years and store in nginx
+        certificate directory
+      ansible.builtin.include_role:
+        name: mirsg.infrastructure.ssl_certificates
+      vars:
+        ssl_certificate: "{{ nginx_new_ssl_certificate }}" # noqa: var-naming[no-role-prefix]
diff --git a/roles/nginx/molecule/resources/verify.yml b/roles/nginx/molecule/resources/verify.yml
index 267189cd..d2c6fcc5 100644
--- a/roles/nginx/molecule/resources/verify.yml
+++ b/roles/nginx/molecule/resources/verify.yml
@@ -4,7 +4,7 @@
   tasks:
     - name: Get server status
       ansible.builtin.uri:
-        url: http://localhost:8080
+        url: https://localhost:8080
         method: GET
         headers:
           Host: molecule.instance.local
diff --git a/roles/nginx/molecule/rocky9/molecule.yml b/roles/nginx/molecule/rocky9/molecule.yml
index 8142a715..e33a343f 100644
--- a/roles/nginx/molecule/rocky9/molecule.yml
+++ b/roles/nginx/molecule/rocky9/molecule.yml
@@ -31,4 +31,4 @@ platforms:
       - 443
       - 8000
     published_ports:
-      - 127.0.0.1:8080:80
+      - 127.0.0.1:8080:443
diff --git a/roles/nginx/tasks/copy_certificates.yml b/roles/nginx/tasks/copy_certificates.yml
new file mode 100644
index 00000000..9f6b8c9b
--- /dev/null
+++ b/roles/nginx/tasks/copy_certificates.yml
@@ -0,0 +1,11 @@
+---
+- name: Copy certificate to new location
+  ansible.builtin.copy:
+    remote_src: true
+    src: "{{ item.src }}"
+    dest: "{{ item.dest }}"
+    owner: "{{ nginx_owner }}"
+    group: "{{ nginx_group }}"
+    mode: "0600"
+    backup: true # Preserve overwritten certificates and keys for rollback
+  with_items: "{{ items }}"
diff --git a/roles/nginx/tasks/main.yml b/roles/nginx/tasks/main.yml
index 5edb101a..263e2d8f 100644
--- a/roles/nginx/tasks/main.yml
+++ b/roles/nginx/tasks/main.yml
@@ -36,38 +36,8 @@
       - nginx-mod-stream
     state: installed
 
-- name: Ensure nginx certs directory exists
-  ansible.builtin.file:
-    path: "{{ nginx_certs_dir }}"
-    owner: "{{ nginx_owner }}"
-    group: "{{ nginx_group }}"
-    state: directory
-    mode: "0700"
-  when: nginx_use_ssl
-
-- name: Copy server certificates to nginx
-  ansible.builtin.copy:
-    remote_src: true
-    src: "{{ item.src }}"
-    dest: "{{ item.dest }}"
-    owner: "{{ nginx_owner }}"
-    group: "{{ nginx_group }}"
-    mode: "0600"
-  with_items:
-    - src: "{{ nginx_server_cert_cache }}"
-      dest: "{{ nginx_ssl_cert_file }}"
-    - src: "{{ nginx_server_key_cache }}"
-      dest: "{{ nginx_ssl_key_file }}"
-  notify: Reload nginx
-  when: nginx_use_ssl
-
-- name:
-    Generate Diffie-Hellman (DH) parameters. Number of {{
-    nginx_diffie_helman_size_bits }}.
-  community.crypto.openssl_dhparam:
-    path: "{{ nginx_dh_params_file }}"
-    size: "{{ nginx_diffie_helman_size_bits }}"
-  notify: Reload nginx
+- name: Copy certificates when SSL is enabled
+  ansible.builtin.include_tasks: ssl_enabled.yml
   when: nginx_use_ssl
 
 - name: Copy nginx config file
diff --git a/roles/nginx/tasks/ssl_enabled.yml b/roles/nginx/tasks/ssl_enabled.yml
new file mode 100644
index 00000000..5cae1270
--- /dev/null
+++ b/roles/nginx/tasks/ssl_enabled.yml
@@ -0,0 +1,99 @@
+---
+- name: Ensure nginx certs directory exists
+  ansible.builtin.file:
+    path: "{{ nginx_certs_dir }}"
+    owner: "{{ nginx_owner }}"
+    group: "{{ nginx_group }}"
+    state: directory
+    mode: "0700"
+
+- name: Stat current SSL certificate
+  ansible.builtin.stat:
+    path: "{{ nginx_ssl_cert_file }}"
+  register: current_cert
+
+- name: Stat cached SSL certificate
+  ansible.builtin.stat:
+    path: "{{ nginx_server_cert_cache }}"
+  register: cached_cert
+
+- name: Check whether the certs exist
+  ansible.builtin.debug:
+    msg:
+      - "Cached nginx cert exists at {{ nginx_server_cert_cache }}: {{
+        cached_cert.stat.exists }}."
+      - "nginx cert exists at {{ nginx_ssl_cert_file }}: {{
+        current_cert.stat.exists }}."
+  failed_when: (not cached_cert.stat.exists) and (not current_cert.stat.exists)
+
+- name: Get current SSL certificate info
+  community.crypto.x509_certificate_info:
+    path: "{{ nginx_ssl_cert_file }}"
+  when: current_cert.stat.exists
+  register: current_cert_info
+
+- name: Get cached SSL certificate info
+  community.crypto.x509_certificate_info:
+    path: "{{ nginx_server_cert_cache }}"
+  when: cached_cert.stat.exists
+  register: cached_cert_info
+
+- name: Copy server certificates from cache if the nginx cert doesn't exist
+  ansible.builtin.include_tasks: copy_certificates.yml
+  vars:
+    items:
+      - src: "{{ nginx_server_cert_cache }}"
+        dest: "{{ nginx_ssl_cert_file }}"
+      - src: "{{ nginx_server_key_cache }}"
+        dest: "{{ nginx_ssl_key_file }}"
+  when:
+    - not current_cert.stat.exists
+    - cached_cert.stat.exists
+
+- name: Copy server certificates to cache if the cache cert doesn't exist
+  ansible.builtin.include_tasks: copy_certificates.yml
+  vars:
+    items:
+      - src: "{{ nginx_ssl_cert_file }}"
+        dest: "{{ nginx_server_cert_cache }}"
+      - src: "{{ nginx_ssl_key_file }}"
+        dest: "{{ nginx_server_key_cache }}"
+  when:
+    - current_cert.stat.exists
+    - not cached_cert.stat.exists
+
+- name: Copy server certificates from cache if the nginx cert expires sooner
+  ansible.builtin.include_tasks: copy_certificates.yml
+  vars:
+    items:
+      - src: "{{ nginx_server_cert_cache }}"
+        dest: "{{ nginx_ssl_cert_file }}"
+      - src: "{{ nginx_server_key_cache }}"
+        dest: "{{ nginx_ssl_key_file }}"
+  when:
+    - current_cert.stat.exists
+    - cached_cert.stat.exists
+    - current_cert_info.not_after | to_datetime('%Y%m%d%H%M%SZ') <
+      cached_cert_info.not_after | to_datetime('%Y%m%d%H%M%SZ')
+
+- name: Copy server certificates to cache if the cache cert expires sooner
+  ansible.builtin.include_tasks: copy_certificates.yml
+  vars:
+    items:
+      - src: "{{ nginx_ssl_cert_file }}"
+        dest: "{{ nginx_server_cert_cache }}"
+      - src: "{{ nginx_ssl_key_file }}"
+        dest: "{{ nginx_server_key_cache }}"
+  when:
+    - current_cert.stat.exists
+    - cached_cert.stat.exists
+    - current_cert_info.not_after | to_datetime('%Y%m%d%H%M%SZ') >
+      cached_cert_info.not_after | to_datetime('%Y%m%d%H%M%SZ')
+
+- name:
+    Generate Diffie-Hellman (DH) parameters. Number of {{
+    nginx_diffie_helman_size_bits }}.
+  community.crypto.openssl_dhparam:
+    path: "{{ nginx_dh_params_file }}"
+    size: "{{ nginx_diffie_helman_size_bits }}"
+  notify: Reload nginx
diff --git a/roles/ssl_certificates/README.md b/roles/ssl_certificates/README.md
index 21a50120..780f0514 100644
--- a/roles/ssl_certificates/README.md
+++ b/roles/ssl_certificates/README.md
@@ -86,15 +86,16 @@ First define variables for the server:
 ```yaml
 # Variables for creating a SSL certificate for a postgresql server
 ssl_certificate:
-  owner: "root"
-  group: "root"
-  certificate_directory: "/var/lib/pgsql/certs"
-  privatekey_filename: "/var/lib/pgsql/certs/server.key"
+  owner: root
+  group: root
+  certificate_directory: /var/lib/pgsql/certs
+  privatekey_filename: /var/lib/pgsql/certs/server.key
   use_pk8: false
-  csr_filename: "/var/lib/pgsql/server.csr"
-  csr_common_name: "db"
-  certificate_filename: "/var/lib/pgsql/server.crt"
-  provider: "selfsigned"
+  csr_filename: /var/lib/pgsql/server.csr
+  csr_common_name: db
+  certificate_filename: /var/lib/pgsql/server.crt
+  provider: selfsigned
+  selfsigned_not_after: +3650d
   cache_filename:
     "{{ lookup('env', 'HOME')
     }}/ansible_persistent_files/pg_certificates/db.postgresql_server.crt"
@@ -108,16 +109,17 @@ client is a tomcat server:
 ```yaml
 # Variables for creating a SSL certificate for a postgresql client
 ssl_certificate:
-  owner: "root"
-  group: "root"
-  certificate_directory: "/usr/share/tomcat/.postgresql"
-  privatekey_filename: "/usr/share/tomcat/.postgresql/postgresql.key"
+  owner: root
+  group: root
+  certificate_directory: /usr/share/tomcat/.postgresql
+  privatekey_filename: /usr/share/tomcat/.postgresql/postgresql.key
   use_pk8: true
-  pk8_filename: "/usr/share/tomcat/.postgresql/postgresql.pk8"
-  csr_filename: "/usr/share/tomcat/.postgresql/postgresql.csr"
+  pk8_filename: /usr/share/tomcat/.postgresql/postgresql.pk8
+  csr_filename: /usr/share/tomcat/.postgresql/postgresql.csr
   csr_common_name: "{{ web_hostname }}"
-  certificate_filename: "/usr/share/tomcat/.postgresql/postgresql.crt"
-  provider: "selfsigned"
+  certificate_filename: /usr/share/tomcat/.postgresql/postgresql.crt
+  provider: selfsigned
+  selfsigned_not_after: +3650d
   cache_filename:
     "{{ lookup('env', 'HOME')
     }}/ansible_persistent_files/pg_certificates/db.postgresql_client.crt"
diff --git a/roles/ssl_certificates/tasks/main.yml b/roles/ssl_certificates/tasks/main.yml
index 636e4fe2..f6cc4884 100644
--- a/roles/ssl_certificates/tasks/main.yml
+++ b/roles/ssl_certificates/tasks/main.yml
@@ -35,6 +35,7 @@
     privatekey_path: "{{ ssl_certificate.privatekey_filename }}"
     csr_path: "{{ ssl_certificate.csr_filename }}"
     provider: "{{ ssl_certificate.provider }}"
+    selfsigned_not_after: "{{ ssl_certificate.selfsigned_not_after }}"
     mode: "0400"
     owner: "{{ ssl_certificate.owner }}"
     group: "{{ ssl_certificate.group }}"
diff --git a/roles/tomcat/defaults/main.yml b/roles/tomcat/defaults/main.yml
index e31ae382..d9fe1814 100644
--- a/roles/tomcat/defaults/main.yml
+++ b/roles/tomcat/defaults/main.yml
@@ -7,7 +7,7 @@ java_home: /usr/lib/jvm/jre
 java_profile_d: /etc/profile.d
 
 # mirsg.tomcat
-tomcat_version: 9.0.82
+tomcat_version: 9.0.97
 tomcat_owner: tomcat
 tomcat_group: tomcat