diff --git a/CHANGELOG.md b/CHANGELOG.md
index 45dff38c..5996a895 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,10 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ### Fixed
 - The `https_proxy` environment variable is recognized as a synonym for
   `HTTPS_PROXY`.
+- When adding a new server, the initial request now includes an
+  Authorization header containing the API key. This is needed
+  for Connect installations behind a proxy that only passes
+  authenticated requests.
 - Common environment directories (`env, venv, .env, .venv`) are no longer
   excluded by name. Environments are detected by the presence of a python
   executable in `bin` or `Scripts` and excluded.
diff --git a/rsconnect/main.py b/rsconnect/main.py
index 5af3128f..e3673d61 100644
--- a/rsconnect/main.py
+++ b/rsconnect/main.py
@@ -351,7 +351,7 @@ def _test_server_and_api(server, api_key, insecure, ca_cert):
     me = None
 
     with cli_feedback("Checking %s" % server):
-        real_server, _ = test_server(api.RSConnectServer(server, None, insecure, ca_data))
+        real_server, _ = test_server(api.RSConnectServer(server, api_key, insecure, ca_data))
 
     real_server.api_key = api_key