diff --git a/roles/deploy_code/tasks/cleanup.yml b/roles/deploy_code/tasks/cleanup.yml
index 5ca473bf..3336b22f 100644
--- a/roles/deploy_code/tasks/cleanup.yml
+++ b/roles/deploy_code/tasks/cleanup.yml
@@ -29,6 +29,16 @@
     - deploy_code.mount_type == "tarball"
   run_once: true
 
+- name: Ensure older SquashFS images are deleted.
+  ansible.builtin.file:
+    path: "{{ build_base_path }}/deploy.sqsh"
+    state: absent
+  when:
+    - deploy_code.mount_sync is defined
+    - deploy_code.mount_sync | length > 1
+    - deploy_code.mount_type == "squashfs"
+  run_once: true
+
 - name: Create a SquashFS image of the deployed codebases.
   ansible.builtin.command:
     cmd: "mksquashfs {{ build_base_path }} /tmp/{{ project_name }}_{{ build_type }}.sqsh"
@@ -74,15 +84,26 @@
     - deploy_code.mount_sync | length > 1
     - deploy_code.mount_type == "squashfs"
 
-- name: Unmount existing SquashFS image.
+- name: Check if we have a mount already.
+  ansible.builtin.command:
+    cmd: "mount | grep {{ deploy_base_path }}"
+  ignore_errors: true
+  register: _mount_check
+  when:
+    - deploy_code.mount_sync is defined
+    - deploy_code.mount_sync | length > 1
+    - deploy_code.mount_type == "squashfs"
+
+- name: Remount existing SquashFS image.
   ansible.builtin.command:
-    cmd: "umount --force {{ deploy_base_path }}"
+    cmd: "mount {{ build_base_path }}/deploy.sqsh {{ deploy_base_path }} -t squashfs -o remount"
   become: true
   become_user: "{{ deploy_user }}"
   when:
     - deploy_code.mount_sync is defined
     - deploy_code.mount_sync | length > 1
     - deploy_code.mount_type == "squashfs"
+    - _mount_check | success
 
 - name: Mount new SquashFS image.
   ansible.builtin.command:
@@ -93,6 +114,7 @@
     - deploy_code.mount_sync is defined
     - deploy_code.mount_sync | length > 1
     - deploy_code.mount_type == "squashfs"
+    - _mount_check | failed
 
 - name: Trigger an infrastructure rebuild.
   ansible.builtin.include_role: