diff --git a/app/Jobs/ApplicationDeploymentJob.php b/app/Jobs/ApplicationDeploymentJob.php
index 41de17b05..dbb91aa24 100644
--- a/app/Jobs/ApplicationDeploymentJob.php
+++ b/app/Jobs/ApplicationDeploymentJob.php
@@ -1632,7 +1632,7 @@ private function health_check()
                 return;
             }
             if ($this->application->custom_healthcheck_found) {
-                $this->application_deployment_queue->addLogEntry('Custom healthcheck found, skipping default healthcheck.');
+                $this->application_deployment_queue->addLogEntry('Custom healthcheck found in Dockerfile.');
             }
             if ($this->container_name) {
                 $counter = 1;
@@ -2358,16 +2358,22 @@ private function generate_compose_file()
         ];
         // Always use .env file
         $docker_compose['services'][$this->container_name]['env_file'] = ['.env'];
-        $docker_compose['services'][$this->container_name]['healthcheck'] = [
-            'test' => [
-                'CMD-SHELL',
-                $this->generate_healthcheck_commands(),
-            ],
-            'interval' => $this->application->health_check_interval.'s',
-            'timeout' => $this->application->health_check_timeout.'s',
-            'retries' => $this->application->health_check_retries,
-            'start_period' => $this->application->health_check_start_period.'s',
-        ];
+
+        // Only add Coolify healthcheck if no custom HEALTHCHECK found in Dockerfile
+        // If custom_healthcheck_found is true, the Dockerfile's HEALTHCHECK will be used
+        // If healthcheck is disabled, no healthcheck will be added
+        if (! $this->application->custom_healthcheck_found && ! $this->application->isHealthcheckDisabled()) {
+            $docker_compose['services'][$this->container_name]['healthcheck'] = [
+                'test' => [
+                    'CMD-SHELL',
+                    $this->generate_healthcheck_commands(),
+                ],
+                'interval' => $this->application->health_check_interval.'s',
+                'timeout' => $this->application->health_check_timeout.'s',
+                'retries' => $this->application->health_check_retries,
+                'start_period' => $this->application->health_check_start_period.'s',
+            ];
+        }
 
         if (! is_null($this->application->limits_cpuset)) {
             data_set($docker_compose, 'services.'.$this->container_name.'.cpuset', $this->application->limits_cpuset);
diff --git a/app/Models/Application.php b/app/Models/Application.php
index 99fbded86..32459f752 100644
--- a/app/Models/Application.php
+++ b/app/Models/Application.php
@@ -1806,6 +1806,19 @@ public function parseHealthcheckFromDockerfile($dockerfile, bool $isInit = false
         $dockerfile = str($dockerfile)->trim()->explode("\n");
         $hasHealthcheck = str($dockerfile)->contains('HEALTHCHECK');
 
+        // Always check if healthcheck was removed, regardless of health_check_enabled setting
+        if (! $hasHealthcheck && $this->custom_healthcheck_found) {
+            // HEALTHCHECK was removed from Dockerfile, reset to defaults
+            $this->custom_healthcheck_found = false;
+            $this->health_check_interval = 5;
+            $this->health_check_timeout = 5;
+            $this->health_check_retries = 10;
+            $this->health_check_start_period = 5;
+            $this->save();
+
+            return;
+        }
+
         if ($hasHealthcheck && ($this->isHealthcheckDisabled() || $isInit)) {
             $healthcheckCommand = null;
             $lines = $dockerfile->toArray();
@@ -1847,14 +1860,6 @@ public function parseHealthcheckFromDockerfile($dockerfile, bool $isInit = false
                     $this->save();
                 }
             }
-        } elseif (! $hasHealthcheck && $this->custom_healthcheck_found) {
-            // HEALTHCHECK was removed from Dockerfile, reset to defaults
-            $this->custom_healthcheck_found = false;
-            $this->health_check_interval = 5;
-            $this->health_check_timeout = 5;
-            $this->health_check_retries = 10;
-            $this->health_check_start_period = 5;
-            $this->save();
         }
     }
 
diff --git a/tests/Unit/ApplicationHealthcheckRemovalTest.php b/tests/Unit/ApplicationHealthcheckRemovalTest.php
new file mode 100644
index 000000000..2ccb6be01
--- /dev/null
+++ b/tests/Unit/ApplicationHealthcheckRemovalTest.php
@@ -0,0 +1,57 @@
+<?php
+
+/**
+ * Tests for parseHealthcheckFromDockerfile method
+ *
+ * NOTE: These tests verify the logic for detecting when a HEALTHCHECK directive
+ * is removed from a Dockerfile. The fix ensures that healthcheck removal is detected
+ * regardless of the health_check_enabled setting.
+ */
+
+use App\Models\Application;
+
+it('detects when HEALTHCHECK is removed from dockerfile', function () {
+    // This test verifies the fix for the bug where Coolify doesn't detect
+    // when a HEALTHCHECK is removed from a Dockerfile, causing deployments to fail.
+
+    $dockerfile = str("FROM nginx:latest\nCOPY . /app\nEXPOSE 80")->trim()->explode("\n");
+
+    // The key fix: hasHealthcheck check happens BEFORE the isHealthcheckDisabled check
+    $hasHealthcheck = str($dockerfile)->contains('HEALTHCHECK');
+
+    // Simulate an application with custom_healthcheck_found = true
+    $customHealthcheckFound = true;
+
+    // The fixed logic: This condition should be true when HEALTHCHECK is removed
+    $shouldReset = ! $hasHealthcheck && $customHealthcheckFound;
+
+    expect($shouldReset)->toBeTrue()
+        ->and($hasHealthcheck)->toBeFalse()
+        ->and($customHealthcheckFound)->toBeTrue();
+});
+
+it('does not reset when HEALTHCHECK exists in dockerfile', function () {
+    $dockerfile = str("FROM nginx:latest\nHEALTHCHECK --interval=30s CMD curl\nEXPOSE 80")->trim()->explode("\n");
+
+    $hasHealthcheck = str($dockerfile)->contains('HEALTHCHECK');
+    $customHealthcheckFound = true;
+
+    // When healthcheck exists, should not reset
+    $shouldReset = ! $hasHealthcheck && $customHealthcheckFound;
+
+    expect($shouldReset)->toBeFalse()
+        ->and($hasHealthcheck)->toBeTrue();
+});
+
+it('does not reset when custom_healthcheck_found is false', function () {
+    $dockerfile = str("FROM nginx:latest\nCOPY . /app\nEXPOSE 80")->trim()->explode("\n");
+
+    $hasHealthcheck = str($dockerfile)->contains('HEALTHCHECK');
+    $customHealthcheckFound = false;
+
+    // When custom_healthcheck_found is false, no need to reset
+    $shouldReset = ! $hasHealthcheck && $customHealthcheckFound;
+
+    expect($shouldReset)->toBeFalse()
+        ->and($customHealthcheckFound)->toBeFalse();
+});