diff --git a/tests_e2e/docker/docker-compose-acme-e2e.yml b/tests_e2e/docker/docker-compose-acme-e2e.yml
index eea991d..01434e7 100644
--- a/tests_e2e/docker/docker-compose-acme-e2e.yml
+++ b/tests_e2e/docker/docker-compose-acme-e2e.yml
@@ -64,22 +64,6 @@ services:
     networks:
       - acme-test
 
-  # Pebble health check sidecar
-  pebble_health:
-    image: curlimages/curl:8.6.0
-    depends_on:
-      - pebble
-    healthcheck:
-      test: ["CMD", "curl", "-skf", "https://pebble:14000/dir"]
-      interval: 2s
-      timeout: 5s
-      start_period: 20s  # Extended startup window for slow CI
-      retries: 30        # Increased retries for CI reliability
-    networks:
-      - acme-test
-    restart: "no"
-    command: ["tail", "-f", "/dev/null"]
-
   # Backend web server
   backend:
     image: byjg/static-httpserver
@@ -98,10 +82,8 @@ services:
       context: ../..
       dockerfile: build/Dockerfile
     depends_on:
-      pebble_health:
-        condition: service_healthy
-      backend:
-        condition: service_started
+      - pebble
+      - backend
     healthcheck:
       test: ["CMD", "curl", "-f", "-u", "admin:password", "http://localhost:1936"]
       interval: 10s
diff --git a/tests_e2e/test_docker_compose.py b/tests_e2e/test_docker_compose.py
index 1c850b7..aa45096 100644
--- a/tests_e2e/test_docker_compose.py
+++ b/tests_e2e/test_docker_compose.py
@@ -34,6 +34,10 @@ import requests
 import jwt as jwt_lib
 from typing import Generator
 from utils import extract_backend_block, DockerComposeFixture
+import urllib3
+
+# Disable SSL warnings for Pebble health checks (self-signed certs)
+urllib3.disable_warnings(urllib3.exceptions.InsecureRequestWarning)
 
 # Base directory for docker-compose files
 BASE_DIR = Path(__file__).parent.absolute()
@@ -843,6 +847,22 @@ class TestChangedLabel:
 # Test: docker-compose-acme-e2e.yml - ACME/Certbot with Pebble
 # =============================================================================
 
+def wait_for_pebble() -> bool:
+    """
+    Health check function to verify Pebble ACME server is ready.
+
+    Returns True if Pebble is responding to the /dir endpoint.
+    This is used instead of Docker healthchecks for more reliable startup
+    detection in CI environments.
+    """
+    try:
+        # Pebble uses self-signed certificates, so we need verify=False
+        response = requests.get("https://127.0.0.1:14000/dir", verify=False, timeout=5)
+        return response.status_code == 200
+    except Exception:
+        return False
+
+
 @pytest.fixture
 def docker_compose_acme() -> Generator[None, None, None]:
     """Fixture for docker-compose-acme-e2e.yml - ACME/Certbot E2E test"""
@@ -858,7 +878,13 @@ def docker_compose_acme() -> Generator[None, None, None]:
         stderr=subprocess.DEVNULL  # Ignore error if volume doesn't exist
     )
 
-    fixture = DockerComposeFixture(str(DOCKER_DIR / "docker-compose-acme-e2e.yml"), startup_wait=0)
+    # Use custom health check for Pebble with generous timeout for CI
+    fixture = DockerComposeFixture(
+        str(DOCKER_DIR / "docker-compose-acme-e2e.yml"),
+        startup_wait=0,
+        health_check=wait_for_pebble,
+        health_check_timeout=90  # Extended timeout for slow CI environments
+    )
     fixture.up()
     yield
     fixture.down()