diff --git a/app/Jobs/ApplicationDeploymentJob.php b/app/Jobs/ApplicationDeploymentJob.php
index 6df9a8623..bcd7a729d 100644
--- a/app/Jobs/ApplicationDeploymentJob.php
+++ b/app/Jobs/ApplicationDeploymentJob.php
@@ -1813,9 +1813,9 @@ private function health_check()
                             $this->application->update(['status' => 'running']);
                             $this->application_deployment_queue->addLogEntry('New container is healthy.');
                             break;
-                        }
-                        if (str($this->saved_outputs->get('health_check'))->replace('"', '')->value() === 'unhealthy') {
+                        }  elseif (str($this->saved_outputs->get('health_check'))->replace('"', '')->value() === 'unhealthy') {
                             $this->newVersionIsHealthy = false;
+                            $this->application_deployment_queue->addLogEntry('New container is unhealthy.', type: 'error');
                             $this->query_logs();
                             break;
                         }
@@ -3187,6 +3187,18 @@ private function stop_running_container(bool $force = false)
                 $this->graceful_shutdown_container($this->container_name);
             }
         } catch (Exception $e) {
+            // If new version is healthy, this is just cleanup - don't fail the deployment
+            if ($this->newVersionIsHealthy || $force) {
+                $this->application_deployment_queue->addLogEntry(
+                    "Warning: Could not remove old container: {$e->getMessage()}",
+                    'stderr',
+                    hidden: true
+                );
+
+                return; // Don't re-throw - cleanup failures shouldn't fail successful deployments
+            }
+
+            // Only re-throw if deployment hasn't succeeded yet
             throw new DeploymentException("Failed to stop running container: {$e->getMessage()}", $e->getCode(), $e);
         }
     }