diff --git a/.ai/lessons.md b/.ai/lessons.md
index 79bac6eff3..06d5343213 100644
--- a/.ai/lessons.md
+++ b/.ai/lessons.md
@@ -57,6 +57,7 @@
 - Use the database as the correctness source for dynamic cron occurrences shared by multiple scheduler and Horizon nodes; Redis locks are load controls, not a durable execution ledger.
 - Give each schedule occurrence a unique database identity and make queue consumers claim it atomically before external work.
 - Keep pending occurrences recoverable across publisher interruptions, and define an explicit bounded policy for late or offline schedules.
+- Horizon workers are long-lived: flush every static or `once()` cache (for example `Server::flushIdentityMap()`) in `Queue::before`, or later jobs decide with stale state.
 
 ## Fail closed at public webhook boundaries
 - Reject missing or blank secrets before signature verification, and return generic errors without logging secrets, signatures, or payloads.
diff --git a/app/Jobs/ApplicationDeploymentJob.php b/app/Jobs/ApplicationDeploymentJob.php
index 6ff61ad9c1..d886c905b9 100644
--- a/app/Jobs/ApplicationDeploymentJob.php
+++ b/app/Jobs/ApplicationDeploymentJob.php
@@ -1031,7 +1031,8 @@ class ApplicationDeploymentJob implements ShouldBeEncrypted, ShouldQueue
     /**
      * The queued ServerStorageSaveJob writes new content files, but it can run after the containers
      * start. Preserve-repository deployments write all file storages in write_deployment_configurations().
-     * Each deployment writes the files on its own server, so additional servers also get them.
+     * Each deployment writes the missing files on its own server before the containers start, so
+     * additional servers also get them.
      */
     private function write_missing_content_files(): void
     {
@@ -4602,8 +4603,14 @@ COPY ./nginx.conf /etc/nginx/conf.d/default.conf");
             ->values();
     }
 
+    /**
+     * `docker compose up` creates a missing bind source as an empty directory, so content files are
+     * written first. This also gives a server that was added later the files it does not have.
+     */
     private function start_by_compose_file()
     {
+        $this->write_missing_content_files();
+
         try {
             // Ensure .env file exists before docker compose tries to load it (defensive programming)
             $this->execute_remote_command(
diff --git a/tests/Feature/ContentFilesBeforeComposeUpTest.php b/tests/Feature/ContentFilesBeforeComposeUpTest.php
index b812ed68f8..2086f9ce88 100644
--- a/tests/Feature/ContentFilesBeforeComposeUpTest.php
+++ b/tests/Feature/ContentFilesBeforeComposeUpTest.php
@@ -361,6 +361,49 @@ test('a deployment to an additional server writes missing content files on that
         ->and(ContentFilesUpRecorder::ssh()[$write])->not->toContain("@'{$this->server->ip}'");
 });
 
+test('a Dockerfile deployment to an additional server writes missing content files before the container starts', function () {
+    $this->application->update(['build_pack' => 'dockerfile', 'docker_compose_location' => null]);
+    $volume = contentFilesVolume($this->application, 'config/app.conf');
+    $otherServer = Server::factory()->create([
+        'team_id' => $this->team->id,
+        'private_key_id' => $this->server->private_key_id,
+    ])->fresh();
+    fakeContentFilesServer([$volume->fs_path => 'missing']);
+
+    $job = new ContentFilesUpDeploymentJob;
+    $queue = Mockery::mock(ApplicationDeploymentQueue::class)->makePartial();
+    $queue->shouldReceive('addLogEntry')->andReturnUsing(function (string $message, string $type = 'stdout') {
+        $this->logEntries[] = [$message, $type];
+    });
+    foreach ([
+        'application' => $this->application->fresh(),
+        'application_deployment_queue' => $queue,
+        'server' => $otherServer,
+        'mainServer' => $otherServer,
+        'deployment_uuid' => 'deployment-uuid',
+        'workdir' => '/artifacts/deployment-uuid',
+        'configuration_dir' => $this->application->workdir(),
+        'docker_compose_location' => '/docker-compose.yaml',
+        'coolify_variables' => '',
+        'pull_request_id' => 0,
+        'preserveRepository' => false,
+        'use_build_server' => false,
+        'saved_outputs' => collect(),
+    ] as $property => $value) {
+        (new ReflectionProperty(ApplicationDeploymentJob::class, $property))->setValue($job, $value);
+    }
+
+    (new ReflectionMethod(ApplicationDeploymentJob::class, 'start_by_compose_file'))->invoke($job);
+
+    $write = ContentFilesUpRecorder::indexOf('ssh', 'base64 -d | tee '.escapeshellarg($volume->fs_path));
+    $up = ContentFilesUpRecorder::indexOf('deployment', ' up --build -d');
+    expect($write)->not->toBeNull()
+        ->and($up)->not->toBeNull()
+        ->and($write)->toBeLessThan($up)
+        ->and(ContentFilesUpRecorder::ssh()[$write])->toContain("@'{$otherServer->ip}'")
+        ->and($this->logEntries)->toContain(['Writing 1 missing configuration file.', 'stdout']);
+});
+
 test('the content file check and write are safe for non-root servers', function () {
     $this->server->update(['user' => 'ubuntu']);
     $volume = contentFilesVolume($this->application, 'config/app.conf');