diff --git a/app/Actions/Server/CleanupDocker.php b/app/Actions/Server/CleanupDocker.php
index cdbe10427..d9b4b5a6b 100644
--- a/app/Actions/Server/CleanupDocker.php
+++ b/app/Actions/Server/CleanupDocker.php
@@ -115,8 +115,10 @@ private function cleanupApplicationImages(Server $server, $applications = null):
             $applications = $server->applications();
         }
 
+        $disableRetention = $server->settings->disable_application_image_retention ?? false;
+
         foreach ($applications as $application) {
-            $imagesToKeep = $application->settings->docker_images_to_keep ?? 2;
+            $imagesToKeep = $disableRetention ? 0 : ($application->settings->docker_images_to_keep ?? 2);
             $imageRepository = $application->docker_registry_image_name ?? $application->uuid;
 
             // Get the currently running image tag
diff --git a/app/Livewire/Project/Application/Rollback.php b/app/Livewire/Project/Application/Rollback.php
index e3223a499..d6b490c79 100644
--- a/app/Livewire/Project/Application/Rollback.php
+++ b/app/Livewire/Project/Application/Rollback.php
@@ -23,10 +23,14 @@ class Rollback extends Component
     #[Validate(['integer', 'min:0', 'max:100'])]
     public int $dockerImagesToKeep = 2;
 
+    public bool $serverRetentionDisabled = false;
+
     public function mount()
     {
         $this->parameters = get_route_parameters();
         $this->dockerImagesToKeep = $this->application->settings->docker_images_to_keep ?? 2;
+        $server = $this->application->destination->server;
+        $this->serverRetentionDisabled = $server->settings->disable_application_image_retention ?? false;
     }
 
     public function saveSettings()
diff --git a/app/Livewire/Server/DockerCleanup.php b/app/Livewire/Server/DockerCleanup.php
index 764e583cd..92094c950 100644
--- a/app/Livewire/Server/DockerCleanup.php
+++ b/app/Livewire/Server/DockerCleanup.php
@@ -31,6 +31,9 @@ class DockerCleanup extends Component
     #[Validate('boolean')]
     public bool $deleteUnusedNetworks = false;
 
+    #[Validate('boolean')]
+    public bool $disableApplicationImageRetention = false;
+
     public function mount(string $server_uuid)
     {
         try {
@@ -52,6 +55,7 @@ public function syncData(bool $toModel = false)
             $this->server->settings->docker_cleanup_threshold = $this->dockerCleanupThreshold;
             $this->server->settings->delete_unused_volumes = $this->deleteUnusedVolumes;
             $this->server->settings->delete_unused_networks = $this->deleteUnusedNetworks;
+            $this->server->settings->disable_application_image_retention = $this->disableApplicationImageRetention;
             $this->server->settings->save();
         } else {
             $this->forceDockerCleanup = $this->server->settings->force_docker_cleanup;
@@ -59,6 +63,7 @@ public function syncData(bool $toModel = false)
             $this->dockerCleanupThreshold = $this->server->settings->docker_cleanup_threshold;
             $this->deleteUnusedVolumes = $this->server->settings->delete_unused_volumes;
             $this->deleteUnusedNetworks = $this->server->settings->delete_unused_networks;
+            $this->disableApplicationImageRetention = $this->server->settings->disable_application_image_retention;
         }
     }
 
diff --git a/app/Models/ServerSetting.php b/app/Models/ServerSetting.php
index 6da4dd4c6..4b33df300 100644
--- a/app/Models/ServerSetting.php
+++ b/app/Models/ServerSetting.php
@@ -61,6 +61,7 @@ class ServerSetting extends Model
         'is_reachable' => 'boolean',
         'is_usable' => 'boolean',
         'is_terminal_enabled' => 'boolean',
+        'disable_application_image_retention' => 'boolean',
     ];
 
     protected static function booted()
diff --git a/database/migrations/2025_12_05_100000_add_disable_application_image_retention_to_server_settings.php b/database/migrations/2025_12_05_100000_add_disable_application_image_retention_to_server_settings.php
new file mode 100644
index 000000000..a2433e5c9
--- /dev/null
+++ b/database/migrations/2025_12_05_100000_add_disable_application_image_retention_to_server_settings.php
@@ -0,0 +1,22 @@
+<?php
+
+use Illuminate\Database\Migrations\Migration;
+use Illuminate\Database\Schema\Blueprint;
+use Illuminate\Support\Facades\Schema;
+
+return new class extends Migration
+{
+    public function up(): void
+    {
+        Schema::table('server_settings', function (Blueprint $table) {
+            $table->boolean('disable_application_image_retention')->default(false);
+        });
+    }
+
+    public function down(): void
+    {
+        Schema::table('server_settings', function (Blueprint $table) {
+            $table->dropColumn('disable_application_image_retention');
+        });
+    }
+};
diff --git a/resources/views/livewire/project/application/rollback.blade.php b/resources/views/livewire/project/application/rollback.blade.php
index 07ca40c56..476712842 100644
--- a/resources/views/livewire/project/application/rollback.blade.php
+++ b/resources/views/livewire/project/application/rollback.blade.php
@@ -7,12 +7,18 @@
     </div>
     <div class="pb-4">You can easily rollback to a previously built (local) images quickly.</div>
 
+    @if($serverRetentionDisabled)
+        <x-callout type="warning" class="mb-4">
+            Image retention is disabled at the server level. This setting has no effect until the server administrator enables it.
+        </x-callout>
+    @endif
+
     <div class="pb-4">
         <form wire:submit="saveSettings" class="flex items-end gap-2 w-96">
             <x-forms.input id="dockerImagesToKeep" type="number" min="0" max="100" label="Images to keep for rollback"
-                helper="Number of Docker images to keep for rollback during cleanup. Set to 0 to only keep the currently running image. PR images are always deleted during cleanup."
-                canGate="update" :canResource="$application" />
-            <x-forms.button canGate="update" :canResource="$application" type="submit">Save</x-forms.button>
+                helper="Number of Docker images to keep for rollback during cleanup. Set to 0 to only keep the currently running image. PR images are always deleted during cleanup.<br><br><strong>Note:</strong> Server administrators can disable image retention at the server level, which overrides this setting."
+                canGate="update" :canResource="$application" :disabled="$serverRetentionDisabled" />
+            <x-forms.button canGate="update" :canResource="$application" type="submit" :disabled="$serverRetentionDisabled">Save</x-forms.button>
         </form>
     </div>
     <div wire:target='loadImages' wire:loading.remove>
diff --git a/resources/views/livewire/server/docker-cleanup.blade.php b/resources/views/livewire/server/docker-cleanup.blade.php
index 8e96bc963..251137fa7 100644
--- a/resources/views/livewire/server/docker-cleanup.blade.php
+++ b/resources/views/livewire/server/docker-cleanup.blade.php
@@ -78,6 +78,10 @@
                                 <li>Networks not attached to running containers will be permanently deleted (networks used by stopped containers are affected).</li>
                                 <li>Containers may lose connectivity if required networks are removed.</li>
                             </ul>" />
+                        <x-forms.checkbox canGate="update" :canResource="$server" instantSave
+                            id="disableApplicationImageRetention"
+                            label="Disable Application Image Retention"
+                            helper="When enabled, Docker cleanup will delete all old application images regardless of per-application retention settings. Only the currently running image will be kept.<br><br><strong>Warning: This disables rollback capabilities for all applications on this server.</strong>" />
                     </div>
                 </div>
             </form>