diff --git a/app/api/views/apple.py b/app/api/views/apple.py
index 119bd29b..8b5125bb 100644
--- a/app/api/views/apple.py
+++ b/app/api/views/apple.py
@@ -9,6 +9,7 @@ from requests import RequestException
 
 from app.api.base import api_bp, require_api_auth
 from app.config import APPLE_API_SECRET, MACAPP_APPLE_API_SECRET
+from app.subscription_webhook import execute_subscription_webhook
 from app.db import Session
 from app.log import LOG
 from app.models import PlanEnum, AppleSubscription
@@ -50,6 +51,7 @@ def apple_process_payment():
 
     apple_sub = verify_receipt(receipt_data, user, password)
     if apple_sub:
+        execute_subscription_webhook(user)
         return jsonify(ok=True), 200
 
     return jsonify(error="Processing failed"), 400
@@ -282,6 +284,7 @@ def apple_update_notification():
             apple_sub.plan = plan
             apple_sub.product_id = transaction["product_id"]
             Session.commit()
+            execute_subscription_webhook(user)
             return jsonify(ok=True), 200
         else:
             LOG.w(
@@ -554,6 +557,7 @@ def verify_receipt(receipt_data, user, password) -> Optional[AppleSubscription]:
             product_id=latest_transaction["product_id"],
         )
 
+    execute_subscription_webhook(user)
     Session.commit()
 
     return apple_sub
diff --git a/app/config.py b/app/config.py
index 782f693d..3818c7d1 100644
--- a/app/config.py
+++ b/app/config.py
@@ -532,3 +532,5 @@ if ENABLE_ALL_REVERSE_ALIAS_REPLACEMENT:
 SKIP_MX_LOOKUP_ON_CHECK = False
 
 DISABLE_RATE_LIMIT = "DISABLE_RATE_LIMIT" in os.environ
+
+SUBSCRIPTION_CHANGE_WEBHOOK = os.environ.get("SUBCRIPTION_CHANGE_WEBHOOK", None)
diff --git a/app/models.py b/app/models.py
index 7a1ad0a8..4b4d6256 100644
--- a/app/models.py
+++ b/app/models.py
@@ -673,6 +673,22 @@ class User(Base, ModelMixin, UserMixin, PasswordOracle):
 
         return None
 
+    def get_active_subscription_end(
+        self, include_partner_subscription: bool = True
+    ) -> Optional[arrow.Arrow]:
+        sub = self.get_active_subscription(
+            include_partner_subscription=include_partner_subscription
+        )
+        if isinstance(sub, Subscription):
+            return arrow.get(sub.next_bill_date)
+        if isinstance(sub, AppleSubscription):
+            return sub.expires_date
+        if isinstance(sub, ManualSubscription):
+            return sub.end_at
+        if isinstance(sub, CoinbaseSubscription):
+            return sub.end_at
+        return None
+
     # region Billing
     def lifetime_or_active_subscription(
         self, include_partner_subscription: bool = True
diff --git a/app/subscription_webhook.py b/app/subscription_webhook.py
new file mode 100644
index 00000000..57952520
--- /dev/null
+++ b/app/subscription_webhook.py
@@ -0,0 +1,33 @@
+import requests
+from requests import RequestException
+
+from app import config
+from app.log import LOG
+from app.models import User
+
+
+def execute_subscription_webhook(user: User):
+    webhook_url = config.SUBSCRIPTION_CHANGE_WEBHOOK
+    if webhook_url is None:
+        return
+    subscription_end = user.get_active_subscription_end(
+        include_partner_subscription=False
+    )
+    sl_subscription_end = None
+    if subscription_end:
+        sl_subscription_end = subscription_end.timestamp
+    payload = {
+        "user_id": user.id,
+        "is_premium": user.is_premium(),
+        "active_subscription_end": sl_subscription_end,
+    }
+    try:
+        response = requests.post(webhook_url, json=payload)
+        if response.status_code == 200:
+            LOG.i("Sent request to subscription update webhook successfully")
+        else:
+            LOG.i(
+                f"Request to webhook failed with statue {response.status_code}: {response.text}"
+            )
+    except RequestException as e:
+        LOG.warn(f"Subscription request exception: {e}")
diff --git a/server.py b/server.py
index c31fb5d6..8ad833f0 100644
--- a/server.py
+++ b/server.py
@@ -79,6 +79,7 @@ from app.config import (
     MEM_STORE_URI,
 )
 from app.dashboard.base import dashboard_bp
+from app.subscription_webhook import execute_subscription_webhook
 from app.db import Session
 from app.developer.base import developer_bp
 from app.discover.base import discover_bp
@@ -491,6 +492,7 @@ def setup_paddle_callback(app: Flask):
                 # in case user cancels a plan and subscribes a new plan
                 sub.cancelled = False
 
+            execute_subscription_webhook(user)
             LOG.d("User %s upgrades!", user)
 
             Session.commit()
@@ -509,6 +511,7 @@ def setup_paddle_callback(app: Flask):
                 ).date()
 
                 Session.commit()
+            execute_subscription_webhook(sub.user)
 
         elif request.form.get("alert_name") == "subscription_cancelled":
             subscription_id = request.form.get("subscription_id")
@@ -538,6 +541,7 @@ def setup_paddle_callback(app: Flask):
                         end_date=request.form.get("cancellation_effective_date"),
                     ),
                 )
+                execute_subscription_webhook(sub.user)
 
             else:
                 # user might have deleted their account
@@ -580,6 +584,7 @@ def setup_paddle_callback(app: Flask):
                 sub.cancelled = False
 
                 Session.commit()
+                execute_subscription_webhook(sub.user)
             else:
                 LOG.w(
                     f"update non-exist subscription {subscription_id}. {request.form}"
@@ -596,6 +601,7 @@ def setup_paddle_callback(app: Flask):
                 Subscription.delete(sub.id)
                 Session.commit()
                 LOG.e("%s requests a refund", user)
+                execute_subscription_webhook(sub.user)
 
         elif request.form.get("alert_name") == "subscription_payment_refunded":
             subscription_id = request.form.get("subscription_id")
@@ -629,6 +635,7 @@ def setup_paddle_callback(app: Flask):
                     LOG.e("Unknown plan_id %s", plan_id)
             else:
                 LOG.w("partial subscription_payment_refunded, not handled")
+            execute_subscription_webhook(sub.user)
 
         return "OK"
 
@@ -742,6 +749,7 @@ def handle_coinbase_event(event) -> bool:
                 coinbase_subscription=coinbase_subscription,
             ),
         )
+    execute_subscription_webhook(user)
 
     return True
 
diff --git a/tests/test_subscription_webhook.py b/tests/test_subscription_webhook.py
new file mode 100644
index 00000000..6b09200c
--- /dev/null
+++ b/tests/test_subscription_webhook.py
@@ -0,0 +1,113 @@
+import http.server
+import json
+import threading
+
+import arrow
+
+from app import config
+from app.models import (
+    Subscription,
+    AppleSubscription,
+    CoinbaseSubscription,
+    ManualSubscription,
+)
+from tests.utils import create_new_user
+
+from app.subscription_webhook import execute_subscription_webhook
+
+http_server = None
+last_http_request = None
+
+
+def setup_module():
+    global http_server
+    http_server = http.server.ThreadingHTTPServer(("", 0), HTTPTestServer)
+    print(http_server.server_port)
+    threading.Thread(target=http_server.serve_forever, daemon=True).start()
+    config.SUBSCRIPTION_CHANGE_WEBHOOK = f"http://localhost:{http_server.server_port}"
+
+
+def teardown_module():
+    global http_server
+    config.SUBSCRIPTION_CHANGE_WEBHOOK = None
+    http_server.shutdown()
+
+
+class HTTPTestServer(http.server.BaseHTTPRequestHandler):
+    def do_POST(self):
+        global last_http_request
+        content_len = int(self.headers.get("Content-Length"))
+        body_data = self.rfile.read(content_len)
+        last_http_request = json.loads(body_data)
+        self.send_response(200)
+
+
+def test_webhook_with_trial():
+    user = create_new_user()
+    execute_subscription_webhook(user)
+    assert last_http_request["user_id"] == user.id
+    assert last_http_request["is_premium"]
+    assert last_http_request["active_subscription_end"] is None
+
+
+def test_webhook_with_subscription():
+    user = create_new_user()
+    end_at = arrow.utcnow().shift(days=1).replace(hour=0, minute=0, second=0)
+    Subscription.create(
+        user_id=user.id,
+        cancel_url="",
+        update_url="",
+        subscription_id="",
+        event_time=arrow.now(),
+        next_bill_date=end_at.date(),
+        plan="yearly",
+        flush=True,
+    )
+    execute_subscription_webhook(user)
+    assert last_http_request["user_id"] == user.id
+    assert last_http_request["is_premium"]
+    assert last_http_request["active_subscription_end"] == end_at.timestamp
+
+
+def test_webhook_with_apple_subscription():
+    user = create_new_user()
+    end_at = arrow.utcnow().shift(days=2).replace(hour=0, minute=0, second=0)
+    AppleSubscription.create(
+        user_id=user.id,
+        receipt_data=arrow.now().date().strftime("%Y-%m-%d"),
+        expires_date=end_at.date().strftime("%Y-%m-%d"),
+        original_transaction_id="",
+        plan="yearly",
+        product_id="",
+        flush=True,
+    )
+    execute_subscription_webhook(user)
+    assert last_http_request["user_id"] == user.id
+    assert last_http_request["is_premium"]
+    assert last_http_request["active_subscription_end"] == end_at.timestamp
+
+
+def test_webhook_with_coinbase_subscription():
+    user = create_new_user()
+    end_at = arrow.utcnow().shift(days=3).replace(hour=0, minute=0, second=0)
+    CoinbaseSubscription.create(
+        user_id=user.id, end_at=end_at.date().strftime("%Y-%m-%d"), flush=True
+    )
+
+    execute_subscription_webhook(user)
+    assert last_http_request["user_id"] == user.id
+    assert last_http_request["is_premium"]
+    assert last_http_request["active_subscription_end"] == end_at.timestamp
+
+
+def test_webhook_with_manual_subscription():
+    user = create_new_user()
+    end_at = arrow.utcnow().shift(days=3).replace(hour=0, minute=0, second=0)
+    ManualSubscription.create(
+        user_id=user.id, end_at=end_at.date().strftime("%Y-%m-%d"), flush=True
+    )
+
+    execute_subscription_webhook(user)
+    assert last_http_request["user_id"] == user.id
+    assert last_http_request["is_premium"]
+    assert last_http_request["active_subscription_end"] == end_at.timestamp