diff --git a/tests/api/v1/generator/base_case.py b/tests/api/v1/generator/base_case.py
index cad0089..a380ed7 100644
--- a/tests/api/v1/generator/base_case.py
+++ b/tests/api/v1/generator/base_case.py
@@ -1,3 +1,4 @@
+from ptero_petri.implementation.petri.webhooks import _retry as retry
 import abc
 import collections
 import errno
@@ -157,7 +158,7 @@ def _assemble_callback_url(self, callback_name, request_data):
         return urlparse.urlunparse((
             'http',
             'localhost:%d' % self.callback_port,
-            '/' + callback_name,
+            '/callbacks/' + callback_name,
             '',
             urllib.urlencode(request_data),
             '',
@@ -197,6 +198,16 @@ def _start_callback_receipt_webserver(self):
                     '--port', str(self.callback_port),
                     ],
                 stdout=subprocess.PIPE, stderr=subprocess.PIPE)
+        self._wait_for_callback_webserver()
+
+    def _wait_for_callback_webserver(self):
+        response = retry(requests.get, self._callback_ping_url())
+        if response.status_code != 200:
+            raise RuntimeError('Failed to spin up callback webserver: %s'
+                    % response.text)
+
+    def _callback_ping_url(self):
+        return 'http://localhost:%d/ping' % self.callback_port
 
     def _stop_callback_receipt_webserver(self):
         _stop_subprocess(self._callback_webserver)
diff --git a/tests/api/v1/generator/callback_webserver.py b/tests/api/v1/generator/callback_webserver.py
index 7e46c64..b519aa5 100755
--- a/tests/api/v1/generator/callback_webserver.py
+++ b/tests/api/v1/generator/callback_webserver.py
@@ -26,7 +26,12 @@ def parse_arguments():
 app = Flask(__name__)
 
 
-@app.route('/<path:callback_name>', methods=['PUT'])
+@app.route('/ping', methods=['GET'])
+def ping():
+    return 'PONG'
+
+
+@app.route('/callbacks/<path:callback_name>', methods=['PUT'])
 def log_request(callback_name):
     try:
         print callback_name