diff --git a/docs/roles/_init.md b/docs/roles/_init.md
index 2f3f43ee..867b8e59 100644
--- a/docs/roles/_init.md
+++ b/docs/roles/_init.md
@@ -16,8 +16,6 @@ deploy_user: deploy # if you are using ce-provision to deploy infrastructure thi
 _mysqldump_params: "--max-allowed-packet=128M --single-transaction --skip-opt -e --quick --skip-disable-keys --skip-add-locks -C -a --add-drop-table"
 # @TODO only used by Drupal 7, can be removed with Drupal 7 deployments
 bin_directory: "/home/{{ deploy_user }}/.bin"
-# Number of dumps/db to look up for cleanup.
-cleanup_history_depth: 50
 install_php_cachetool: true # set to false if you don't need cachetool, e.g. for a nodejs app
 ce_deploy_version: 1.x
 ce_provision_version: 2.x # the version of ce-provision to grab files from when roles are shared
diff --git a/roles/_init/README.md b/roles/_init/README.md
index 2f3f43ee..867b8e59 100644
--- a/roles/_init/README.md
+++ b/roles/_init/README.md
@@ -16,8 +16,6 @@ deploy_user: deploy # if you are using ce-provision to deploy infrastructure thi
 _mysqldump_params: "--max-allowed-packet=128M --single-transaction --skip-opt -e --quick --skip-disable-keys --skip-add-locks -C -a --add-drop-table"
 # @TODO only used by Drupal 7, can be removed with Drupal 7 deployments
 bin_directory: "/home/{{ deploy_user }}/.bin"
-# Number of dumps/db to look up for cleanup.
-cleanup_history_depth: 50
 install_php_cachetool: true # set to false if you don't need cachetool, e.g. for a nodejs app
 ce_deploy_version: 1.x
 ce_provision_version: 2.x # the version of ce-provision to grab files from when roles are shared
diff --git a/roles/_init/defaults/main.yml b/roles/_init/defaults/main.yml
index 24cc103f..d9e4fdf4 100644
--- a/roles/_init/defaults/main.yml
+++ b/roles/_init/defaults/main.yml
@@ -5,8 +5,6 @@ deploy_user: deploy # if you are using ce-provision to deploy infrastructure thi
 _mysqldump_params: "--max-allowed-packet=128M --single-transaction --skip-opt -e --quick --skip-disable-keys --skip-add-locks -C -a --add-drop-table"
 # @TODO only used by Drupal 7, can be removed with Drupal 7 deployments
 bin_directory: "/home/{{ deploy_user }}/.bin"
-# Number of dumps/db to look up for cleanup.
-cleanup_history_depth: 50
 install_php_cachetool: true # set to false if you don't need cachetool, e.g. for a nodejs app
 ce_deploy_version: 1.x
 ce_provision_version: 2.x # the version of ce-provision to grab files from when roles are shared
diff --git a/roles/_init/tasks/main.yml b/roles/_init/tasks/main.yml
index 8c8e8c25..4437ab1c 100644
--- a/roles/_init/tasks/main.yml
+++ b/roles/_init/tasks/main.yml
@@ -131,6 +131,67 @@
         path: "{{ build_base_path }}"
         state: directory
 
+# Calculate the builds to cleanup once here, so we don't do it many times later.
+- name: Calculate builds to cleanup.
+  when: deploy_operation == 'cleanup'
+  block:
+    - name: Initialise list variables for directory reading.
+      ansible.builtin.set_fact:
+        _build_directory_names: []
+        _build_numbers: []
+        _build_numbers_clean: []
+        _build_numbers_to_delete: []
+
+    - name: Find all directories in this project deploy directory.
+      ansible.builtin.find:
+        paths: "{{ deploy_base_path }}"
+        recurse: false
+        file_type: directory
+      register: _build_directories_general
+
+    - name: Find all directories in the build directory if SquashFS.
+      ansible.builtin.find:
+        paths: "{{ build_base_path }}"
+        recurse: false
+        file_type: directory
+      register: _build_directories_squashfs
+      when:
+        - deploy_code.mount_type is defined
+        - deploy_code.mount_type == "squashfs"
+
+    - name: Copy build directories into consistently named variable.
+      ansible.builtin.set_fact:
+        _build_directories: "{{ _build_directories_general }}"
+
+    - name: Replace build directories variable if this is a SquashFS build.
+      ansible.builtin.set_fact:
+        _build_directories: "{{ _build_directories_squashfs }}"
+      when:
+        - deploy_code.mount_type is defined
+        - deploy_code.mount_type == "squashfs"
+
+    - name: Build a list of build numbers.
+      ansible.builtin.set_fact:
+        _build_numbers: "{{ _build_numbers + [item.path | regex_search('^(.*)_([0-9]*)$', '\\2')] }}"
+      with_items: "{{ _build_directories.files }}"
+
+    - name: Convert the list of build numbers to integers.
+      ansible.builtin.set_fact:
+        _build_numbers_clean: "{{ _build_numbers_clean + [item | int] }}"
+      with_items: "{{ _build_numbers }}"
+
+    - name: Order the list of build numbers.
+      ansible.builtin.set_fact:
+        _build_numbers_clean: "{{ _build_numbers_clean | sort }}"
+
+    - name: Build a list of builds to delete.
+      ansible.builtin.set_fact:
+        _build_numbers_to_delete: "{{ _build_numbers_to_delete + [item] }}"
+      with_items: "{{ _build_numbers_clean }}"
+      when: _build_directory_index < (_build_directories.matched - deploy_code.keep)
+      loop_control:
+        index_var: _build_directory_index
+
 - name: Set the previous deploy's path for later use where we need to manipulate the live site.
   ansible.builtin.set_fact:
     previous_deploy_path: "{{ previous_deploy_path | default('{{ deploy_path_prefix }}{{ previous_build_number }}') }}"
diff --git a/roles/database_backup/database_backup-mysql/tasks/cleanup-dump.yml b/roles/database_backup/database_backup-mysql/tasks/cleanup-dump.yml
index 734aad4d..35910475 100644
--- a/roles/database_backup/database_backup-mysql/tasks/cleanup-dump.yml
+++ b/roles/database_backup/database_backup-mysql/tasks/cleanup-dump.yml
@@ -1,8 +1,7 @@
 ---
-# We assume it's safe to only go back 50 build back.
-- name: Delete mysql dumps.
+- name: Delete MySQL dumps.
   ansible.builtin.file:
     path: "{{ mysql_backup.dumps_directory }}/{{ _mysql_host }}/{{ database.database }}-{{ item }}.sql.*"
     state: absent
-  with_sequence: start={{ [previous_build_number | int - cleanup_history_depth, 0] | max }}  end={{ [previous_build_number | int - mysql_backup.keep, 0] | max }}
+  with_items: "{{ _build_numbers_to_delete }}"  # set in _init role
   run_once: true
diff --git a/roles/database_backup/database_backup-mysql/tasks/cleanup-rolling.yml b/roles/database_backup/database_backup-mysql/tasks/cleanup-rolling.yml
index a94ccc2a..058ee80c 100644
--- a/roles/database_backup/database_backup-mysql/tasks/cleanup-rolling.yml
+++ b/roles/database_backup/database_backup-mysql/tasks/cleanup-rolling.yml
@@ -1,5 +1,5 @@
 ---
-- name: Delete mysql databases.
+- name: Delete MySQL databases.
   community.mysql.mysql_db:
     name: "{{ database.database }}_{{ item }}"
     state: absent
@@ -7,5 +7,5 @@
     login_user: "{{ _mysql_user }}"
     login_password: "{{ _mysql_password }}"
     login_unix_socket: "{{ mysql_backup.mysql_unix_socket | default(omit) }}"
-  with_sequence: start={{ [previous_build_number | int - cleanup_history_depth, 0] | max }}  end={{ [previous_build_number | int - mysql_backup.keep, 0] | max }}
+  with_items: "{{ _build_numbers_to_delete }}"  # set in _init role
   run_once: true
diff --git a/roles/database_backup/database_backup-mysql/tasks/cleanup.yml b/roles/database_backup/database_backup-mysql/tasks/cleanup.yml
index 23654247..c999b937 100644
--- a/roles/database_backup/database_backup-mysql/tasks/cleanup.yml
+++ b/roles/database_backup/database_backup-mysql/tasks/cleanup.yml
@@ -16,7 +16,7 @@
 - ansible.builtin.include_tasks: "cleanup-{{ mysql_backup.handling }}.yml"
   when: database.is_replica is not defined
 
-- name: Delete mysql users.
+- name: Delete MySQL users.
   community.mysql.mysql_user:
     name: "{{ database.user }}_{{ item }}"
     host_all: true
@@ -24,7 +24,7 @@
     login_host: "{{ _mysql_host }}"
     login_user: "{{ _mysql_user }}"
     login_password: "{{ _mysql_password }}"
-  with_sequence: start={{ [previous_build_number | int - cleanup_history_depth, 0] | max }}  end={{ [previous_build_number | int - mysql_backup.keep, 0] | max }}
+  with_items: "{{ _build_numbers_to_delete }}"  # set in _init role
   when:
     - mysql_backup.credentials_handling == 'rotate'
     - database.is_replica is not defined
diff --git a/roles/deploy_code/tasks/cleanup.yml b/roles/deploy_code/tasks/cleanup.yml
index 4a05a955..9f521dd4 100644
--- a/roles/deploy_code/tasks/cleanup.yml
+++ b/roles/deploy_code/tasks/cleanup.yml
@@ -1,8 +1,8 @@
 ---
 - name: Ensure codebase is writable.
   ansible.builtin.shell:
-    cmd: "if [ -d {{ deploy_path_prefix }}{{ item }} ]; then chmod -R 777 {{ deploy_path_prefix }}{{ item }}; fi"
-  with_sequence: start={{ [previous_build_number | int - cleanup_history_depth, 0] | max }}  end={{ [previous_build_number | int - deploy_code.keep, 0] | max }}
+    cmd: "if [ -d {{ item.path }} ]; then chmod -R 777 {{ item.path }}; fi"
+  with_items: "{{ _build_directories.files }}"  # set in _init role
   become: true
   when:
     - "www_user != deploy_user"
@@ -10,20 +10,30 @@
 
 - name: Ensure permissions are set on deploy directory.
   ansible.builtin.shell:
-    cmd: "if [ -d {{ deploy_path_prefix }}{{ item }}/{{ deploy_code.perms_fix_path }} ]; then chmod 755 {{ deploy_path_prefix }}{{ item }}/{{ deploy_code.perms_fix_path }}; fi"
-  with_sequence: start={{ [previous_build_number | int - cleanup_history_depth, 0] | max }}  end={{ [previous_build_number | int - deploy_code.keep, 0] | max }}
+    cmd: "if [ -d {{ item.path }} ]; then chmod 755 {{ item.path }}; fi"
+  with_items: "{{ _build_directories.files }}"  # set in _init role
   when:
     - deploy_code.perms_fix_path is defined
     - deploy_code.perms_fix_path | length > 1
     - deploy_code.mount_type != "squashfs"
 
+- name: Initialise list variable for directory deleting.
+  ansible.builtin.set_fact:
+    _build_directories_to_delete: []
+
 - name: Delete codebases from deploy directory.
-  ansible.builtin.file:
-    name: "{{ deploy_path_prefix }}{{ item }}"
-    state: absent
-  with_sequence: start={{ [previous_build_number | int - cleanup_history_depth, 0] | max }}  end={{ [previous_build_number | int - deploy_code.keep, 0] | max }}
-  when:
-    - deploy_code.mount_type != "squashfs"
+  when: deploy_code.mount_type != "squashfs"
+  block:
+    - name: Build a list of directories to delete.
+      ansible.builtin.set_fact:
+        _build_directories_to_delete: "{{ _build_directories_to_delete + [deploy_path_prefix + item|string] }}"
+      with_items: "{{ _build_numbers_to_delete }}"  # set in _init role
+
+    - name: Delete the directories.
+      ansible.builtin.file:
+        name: "{{ item }}"
+        state: absent
+      with_items: "{{ _build_directories_to_delete }}"
 
 - name: Create a tarball of the deployed codebases.
   ansible.builtin.command:
@@ -55,20 +65,29 @@
 
 # Beginning of the squashFS block.
 - name: Execute tasks for squashFS mount type.
+  when:
+    - deploy_code.mount_sync is defined
+    - deploy_code.mount_sync | length > 1
+    - deploy_code.mount_type == "squashfs"
   block:
     - name: Ensure permissions are set on builds directory.
       ansible.builtin.shell:
-        cmd: "if [ -d {{ build_path_prefix }}{{ item }}/{{ deploy_code.perms_fix_path }} ]; then chmod 755 {{ build_path_prefix }}{{ item }}/{{ deploy_code.perms_fix_path }}; fi"
-      with_sequence: start={{ [previous_build_number | int - cleanup_history_depth, 0] | max }}  end={{ [previous_build_number | int - deploy_code.keep, 0] | max }}
+        cmd: "if [ -d {{ item.path }} ]; then chmod 755 {{ item.path }}; fi"
+      with_items: "{{ _build_directories.files }}"  # set in _init role
       when:
         - deploy_code.perms_fix_path is defined
         - deploy_code.perms_fix_path | length > 1
 
-    - name: Delete codebases from builds directory.
+    - name: Build a list of directories to delete.
+      ansible.builtin.set_fact:
+        _build_directories_to_delete: "{{ _build_directories_to_delete + [build_path_prefix + item|string] }}"
+      with_items: "{{ _build_numbers_to_delete }}"  # set in _init role
+
+    - name: Delete the directories.
       ansible.builtin.file:
-        name: "{{ build_path_prefix }}{{ item }}"
+        name: "{{ item }}"
         state: absent
-      with_sequence: start={{ [previous_build_number | int - cleanup_history_depth, 0] | max }}  end={{ [previous_build_number | int - deploy_code.keep, 0] | max }}
+      with_items: "{{ _build_directories_to_delete }}"
 
     - name: Create a SquashFS image of the deployed codebases.
       ansible.builtin.command:
@@ -200,10 +219,6 @@
         - _deploy_code_mount_check.rc == 0
         - deploy_code.service_action == "stop"
         - deploy_code.services | length > 0
-  when:
-    - deploy_code.mount_sync is defined
-    - deploy_code.mount_sync | length > 1
-    - deploy_code.mount_type == "squashfs"
 # End of the squashFS block.
 
 - name: Trigger an infrastructure rebuild.