diff --git a/Dockerfile b/Dockerfile
index 80f6d6e..6c76228 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -4,6 +4,8 @@ FROM python:3.11.5-slim
 ARG DOCKER_METADATA_OUTPUT_JSON='{}'
 ENV DOCKER_METADATA_OUTPUT_JSON=${DOCKER_METADATA_OUTPUT_JSON}
 
+RUN apt-get update && apt-get install -y curl
+
 COPY requirements.txt /app/
 WORKDIR /app
 
@@ -11,4 +13,6 @@ RUN pip install -r requirements.txt
 
 COPY . /app
 
+HEALTHCHECK --interval=10s --timeout=5s --retries=3 CMD curl --fail http://localhost:5000/health || exit 1
+
 CMD ["python", "/app/app.py"]
diff --git a/README.md b/README.md
index ee9ca90..29e32a3 100644
--- a/README.md
+++ b/README.md
@@ -4,7 +4,7 @@ This repo is derived from the [official example](https://github.com/getsentry/ex
 
 ```bash
 docker build -t sentry-tunnel .
-docker run --rm -it --name sentry-tunnel -v $(pwd):/app -e ALLOWED_SENTRY_HOSTS=o123123123.ingest.sentry.io -e ALLOWED_SENTRY_PROJECT_IDS=456456456 -e PORT=5001 -p 5001:5001 sentry-tunnel
+docker run --rm -it --name sentry-tunnel -v $(pwd):/app -e ALLOWED_SENTRY_HOSTS=o123123123.ingest.sentry.io -e ALLOWED_SENTRY_PROJECT_IDS=456456456 -e DEPLOYMENT_ENVIRONMENT=dev -e SENTRY_DSN=<optional> -p 5000:5000 sentry-tunnel
 ```
 
 Below is the original README:
diff --git a/app.py b/app.py
index b3a4647..186a7fa 100644
--- a/app.py
+++ b/app.py
@@ -10,8 +10,8 @@
 import requests
 import sentry_sdk
 from sentry_sdk.integrations.logging import LoggingIntegration
-from sentry_sdk.crons import monitor
-
+from sentry_sdk.crons import capture_checkin
+from sentry_sdk.crons.consts import MonitorStatus
 
 ALLOWED_SENTRY_HOSTS = set([s.strip() for s in os.environ.get("ALLOWED_SENTRY_HOSTS", "").split(",") if s.strip()])
 ALLOWED_SENTRY_PROJECT_IDS = set([s.strip() for s in os.environ.get("ALLOWED_SENTRY_PROJECT_IDS", "").split(",") if s.strip()])
@@ -151,24 +151,25 @@ def build_info():
 @app.route("/health")
 def health():
     current_time = time.time()
-    # Ping Sentry at least every minute. Using a 30s buffer to be safe.
-    if IS_SENTRY_ENABLED and current_time - state["sentry_cron_last_ping_time"] > 30:
+    success = True
+    # Assuming the /health endpoint is called every 10 seconds, ping Sentry at least every minute.
+    if IS_SENTRY_ENABLED and current_time - state["sentry_cron_last_ping_time"] > 50:
         state["sentry_cron_last_ping_time"] = current_time
-        ping_sentry()
+        capture_checkin(
+            monitor_slug='sentry-tunnel',
+            status=MonitorStatus.OK if success else MonitorStatus.ERROR,
+            monitor_config={
+                "schedule": { "type": "interval", "value": 1, "unit": "minute" },
+                "checkin_margin": 5, # minutes
+                "max_runtime": 1, # minutes
+                "failure_issue_threshold": 1,
+                "recovery_threshold": 2,
+            }
+        )
+        logging.info(f"Pinged Sentry CRON with status {'OK' if success else 'ERROR'}")
 
     return "OK"
 
-# Sentry CRON docs: https://docs.sentry.io/platforms/python/crons/
-@monitor(monitor_slug='sentry-tunnel', monitor_config={
-    "schedule": { "type": "interval", "value": 1, "unit": "minute" },
-    "checkin_margin": 5, # minutes
-    "max_runtime": 1, # minutes
-    "failure_issue_threshold": 1,
-    "recovery_threshold": 2,
-})
-def ping_sentry():
-    logging.info("Pinged Sentry CRON")
-
 @app.get("/runtime-info")
 def read_runtime_info():
     return {