diff --git a/app/Jobs/ApplicationDeploymentJob.php b/app/Jobs/ApplicationDeploymentJob.php
index 580d1743e..8ffaabde5 100644
--- a/app/Jobs/ApplicationDeploymentJob.php
+++ b/app/Jobs/ApplicationDeploymentJob.php
@@ -1005,6 +1005,10 @@ private function should_skip_build()
                 $this->skip_build = true;
                 $this->application_deployment_queue->addLogEntry("Image found ({$this->production_image_name}) with the same Git Commit SHA. Build step skipped.");
                 $this->generate_compose_file();
+
+                // Save runtime environment variables even when skipping build
+                $this->save_runtime_environment_variables();
+
                 $this->push_to_docker_registry();
                 $this->rolling_update();
 
@@ -1014,6 +1018,10 @@ private function should_skip_build()
                 $this->application_deployment_queue->addLogEntry("No configuration changed & image found ({$this->production_image_name}) with the same Git Commit SHA. Build step skipped.");
                 $this->skip_build = true;
                 $this->generate_compose_file();
+
+                // Save runtime environment variables even when skipping build
+                $this->save_runtime_environment_variables();
+
                 $this->push_to_docker_registry();
                 $this->rolling_update();
 
@@ -1694,7 +1702,7 @@ private function create_workdir()
         }
     }
 
-    private function prepare_builder_image()
+    private function prepare_builder_image(bool $firstTry = true)
     {
         $this->checkForCancellation();
         $settings = instanceSettings();
@@ -1717,7 +1725,12 @@ private function prepare_builder_image()
                 $runCommand = "docker run -d --network {$this->destination->network} --name {$this->deployment_uuid} {$env_flags} --rm -v /var/run/docker.sock:/var/run/docker.sock {$helperImage}";
             }
         }
-        $this->application_deployment_queue->addLogEntry("Preparing container with helper image: $helperImage.");
+        if ($firstTry) {
+            $this->application_deployment_queue->addLogEntry("Preparing container with helper image: $helperImage");
+        } else {
+            $this->application_deployment_queue->addLogEntry('Preparing container with helper image with updated envs.');
+        }
+
         $this->graceful_shutdown_container($this->deployment_uuid);
         $this->execute_remote_command(
             [
@@ -1740,7 +1753,7 @@ private function restart_builder_container_with_actual_commit()
         $this->env_args = null;
 
         // Restart the helper container with updated environment variables (including actual SOURCE_COMMIT)
-        $this->prepare_builder_image();
+        $this->prepare_builder_image(firstTry: false);
     }
 
     private function deploy_to_additional_destinations()