diff --git a/roles/_init/tasks/drupal7.yml b/roles/_init/tasks/drupal7.yml
index 3053c5c4..f6919125 100644
--- a/roles/_init/tasks/drupal7.yml
+++ b/roles/_init/tasks/drupal7.yml
@@ -11,7 +11,7 @@
   import_role:
     name: cli/drush
 
-- name: Ensure we have a cachetool binary.
+- name: Ensure we have a cachetool binary and configuration.
   ansible.builtin.import_role:
     name: cli/cachetool
   when: install_php_cachetool
diff --git a/roles/_init/tasks/drupal8.yml b/roles/_init/tasks/drupal8.yml
index c254ffd6..afd1217b 100644
--- a/roles/_init/tasks/drupal8.yml
+++ b/roles/_init/tasks/drupal8.yml
@@ -11,9 +11,7 @@
   ansible.builtin.set_fact:
     drush_live_bin: "{{ drush_live_bin | default('{{ live_symlink_dest }}/vendor/bin/drush') }}"
 
-- name: Ensure we have a cachetool binary.
+- name: Ensure we have a cachetool binary and configuration.
   ansible.builtin.import_role:
     name: cli/cachetool
-  when:
-    - install_php_cachetool
-    - deploy_operation == 'deploy'
+  when: install_php_cachetool
diff --git a/roles/cli/cachetool/tasks/main.yml b/roles/cli/cachetool/tasks/main.yml
index e7035c7c..d3a21cb2 100644
--- a/roles/cli/cachetool/tasks/main.yml
+++ b/roles/cli/cachetool/tasks/main.yml
@@ -1,17 +1,16 @@
 ---
-- name: Remove previous cachetool if exists.
-  ansible.builtin.file:
-    path: "{{ cachetool_bin }}"
-    state: absent
-  when:
-    - deploy_operation == 'deploy'
+- name: Initial housekeeping tasks.
+  when: deploy_operation == 'deploy'
+  block:
+    - name: Remove previous cachetool if exists.
+      ansible.builtin.file:
+        path: "{{ cachetool_bin }}"
+        state: absent
 
-- name: Ensure bin directory exists.
-  ansible.builtin.file:
-    path: "{{ cachetool_bin | dirname }}"
-    state: directory
-  when:
-    - deploy_operation == 'deploy'
+    - name: Ensure bin directory exists.
+      ansible.builtin.file:
+        path: "{{ cachetool_bin | dirname }}"
+        state: directory
 
 - name: Download cachetool depending on latest php version installed. # If not specified manually, according to https://github.com/gordalina/cachetool#compatibility
   when:
@@ -84,7 +83,7 @@
     - cachetool.version is defined
     - cachetool.version | length > 0
 
-# Set up cachetool adapter
+# Set up cachetool adapter - needs to happen on every run so _cachetool_adapter is set.
 - name: Get latest PHP version installed.
   ansible.builtin.shell:
     cmd: 'set -o pipefail && ls -1 /etc/php/ | while read ver; do if [ -d "/etc/php/$ver/fpm" ]; then echo "$ver"; fi; done | tail -1'