diff --git a/hc/api/tests/test_notify.py b/hc/api/tests/test_notify.py
index 024eb145..b195ac53 100644
--- a/hc/api/tests/test_notify.py
+++ b/hc/api/tests/test_notify.py
@@ -91,6 +91,18 @@ class NotifyTestCase(BaseTestCase):
         self.assertEqual(kwargs["headers"], {"User-Agent": "healthchecks.io"})
         self.assertEqual(kwargs["timeout"], 5)
 
+    @patch("hc.api.transports.requests.request")
+    def test_webhooks_handle_variable_variables(self, mock_get):
+        self._setup_data("webhook", "http://host/$$NAMETAG1")
+        self.check.tags = "foo bar"
+        self.check.save()
+
+        self.channel.notify(self.check)
+
+        # $$NAMETAG1 should *not* get transformed to "foo"
+        args, kwargs = mock_get.call_args
+        self.assertEqual(args[1], "http://host/$TAG1")
+
     @patch("hc.api.transports.requests.request")
     def test_webhooks_support_post(self, mock_request):
         template = "http://example.com\n\nThe Time Is $NOW"
diff --git a/hc/api/transports.py b/hc/api/transports.py
index f849c460..ac464662 100644
--- a/hc/api/transports.py
+++ b/hc/api/transports.py
@@ -188,39 +188,23 @@ class HttpTransport(Transport):
 
 class Webhook(HttpTransport):
     def prepare(self, template, check, urlencode=False):
-        """ Replace variables with actual values.
-
-        There should be no bad translations if users use $ symbol in
-        check's name or tags, because $ gets urlencoded to %24
-
-        """
+        """ Replace variables with actual values. """
 
         def safe(s):
             return quote(s) if urlencode else s
 
-        result = template
-        if "$CODE" in result:
-            result = result.replace("$CODE", str(check.code))
+        ctx = {
+            "$CODE": str(check.code),
+            "$STATUS": check.status,
+            "$NOW": safe(timezone.now().replace(microsecond=0).isoformat()),
+            "$NAME": safe(check.name),
+            "$TAGS": safe(check.tags),
+        }
 
-        if "$STATUS" in result:
-            result = result.replace("$STATUS", check.status)
+        for i, tag in enumerate(check.tags_list()):
+            ctx["$TAG%d" % (i + 1)] = safe(tag)
 
-        if "$NOW" in result:
-            s = timezone.now().replace(microsecond=0).isoformat()
-            result = result.replace("$NOW", safe(s))
-
-        if "$NAME" in result:
-            result = result.replace("$NAME", safe(check.name))
-
-        if "$TAGS" in result:
-            result = result.replace("$TAGS", safe(check.tags))
-
-        if "$TAG" in result:
-            for i, tag in enumerate(check.tags_list()):
-                placeholder = "$TAG%d" % (i + 1)
-                result = result.replace(placeholder, safe(tag))
-
-        return result
+        return replace(template, ctx)
 
     def is_noop(self, check):
         if check.status == "down" and not self.channel.url_down: