diff --git a/roles/mail_server/molecule/default/prepare.yml b/roles/mail_server/molecule/default/prepare.yml
index 51f28bdf518207435a35dc6c5655b3a2b7f748fc..ef47bf6dae35eb45fcf6e05fb1e3ce0236c61c2c 100644
--- a/roles/mail_server/molecule/default/prepare.yml
+++ b/roles/mail_server/molecule/default/prepare.yml
@@ -38,6 +38,15 @@
         - name: parameters-optional-bullseye_smtp
           fqdn: parameters-optional-bullseye
 
+        - name: parameters-mandatory-bookworm_imap
+          fqdn: parameters-mandatory-bookworm
+        - name: parameters-mandatory-bookworm_smtp
+          fqdn: parameters-mandatory-bookworm
+        - name: parameters-optional-bookworm_imap
+          fqdn: parameters-optional-bookworm
+        - name: parameters-optional-bookworm_smtp
+          fqdn: parameters-optional-bookworm
+
     - name: Set-up link to generated X.509 material
       file:
         src: ".gimmecert"
@@ -195,24 +204,95 @@
         192.168.56.51: "parameters-mandatory parameters-mandatory-bullseye"
         192.168.56.52: "parameters-optional parameters-optional-bullseye"
 
+- hosts: bookworm
+  become: true
+  tasks:
+
+    - name: Enable TLSv1.0+ in global OpenSSL configuration file in order to be able to test the web_server_tls_protocols parameter
+      blockinfile:
+        path: "/etc/ssl/openssl.cnf"
+        block: |
+          [openssl_init]
+          ssl_conf = ssl_sect
+
+          [ssl_sect]
+          system_default = system_default_sect
+
+          [system_default_sect]
+          MinProtocol = TLSv1.1
+          CipherString = DEFAULT@SECLEVEL=0
+        owner: root
+        group: root
+        mode: 0644
+        state: present
+
+    - name: Set-up the hosts file
+      lineinfile:
+        path: /etc/hosts
+        regexp: "^{{ item.key }}"
+        line: "{{ item.key }} {{ item.value }}"
+        owner: root
+        group: root
+        mode: 0644
+        state: present
+      with_dict:
+        # Force mail servers to use local ClamAV database mirror.
+        192.168.56.11: "db.local.clamav.net database.clamav.net"
+        192.168.56.12: "ldap-server backup-server"
+        192.168.56.21: "client1 smtp-server-requiring-tls"
+        192.168.56.22: "client2 smtp-server-refusing-tls"
+        192.168.56.31: "parameters-mandatory parameters-mandatory-bookworm"
+        192.168.56.32: "parameters-optional parameters-optional-bookworm"
+
 - hosts: client
   become: true
   tasks:
 
-    - name: Install SWAKS for testing SMTP capability
+    - name: Install tool for testing SMTP capability
       apt:
         name: swaks
         state: present
 
-    - name: Install pip
-      apt:
-        name: python3-pip
-        state: present
+    - name: Install tool for testing IMAP
+      block:
 
-    - name: Install IMAP CLI tool
-      pip:
-        name: Imap-CLI==0.7
-        state: present
+        - name: Install required system packages
+          apt:
+            name: python3-venv
+            state: present
+
+        - name: Set-up dedicated Python virtual environment for running the tool
+          command: "python3 -m venv /opt/imap-cli"
+          args:
+            creates: /opt/imap-cli/bin/python
+
+        - name: Install IMAP CLI
+          pip:
+            name:
+              - Imap-CLI==0.7
+              - six
+            state: present
+            virtualenv: /opt/imap-cli
+
+        - name: Set-up symlinks for running the tool
+          file:
+            src: "/opt/imap-cli/bin/{{ item }}"
+            dest: "/usr/local/bin/{{ item }}"
+            owner: root
+            group: root
+            state: link
+          with_items:
+            - imapcli
+            - imap-cli-flag
+            - imap-cli-delete
+            - imap-cli-copy
+            - imap-api
+            - imap-shell
+            - imap-notify
+            - imap-cli-status
+            - imap-cli-search
+            - imap-cli-read
+            - imap-cli-list
 
     - name: Install tool for testing SIEVE
       apt: