diff --git a/test/thousand_island/server_test.exs b/test/thousand_island/server_test.exs
index dc059fe..08a0878 100644
--- a/test/thousand_island/server_test.exs
+++ b/test/thousand_island/server_test.exs
@@ -375,6 +375,8 @@ defmodule ThousandIsland.ServerTest do
           cacertfile: Path.join(__DIR__, "../support/ca.pem")
         )
 
+      Process.sleep(100)
+
       ThousandIsland.stop(server_pid)
 
       assert_received {:options, {:certfile, _, _}}
@@ -407,6 +409,9 @@ defmodule ThousandIsland.ServerTest do
           ]
         )
 
+      # Negotiation failures seem to take longer
+      Process.sleep(500)
+
       ThousandIsland.stop(server_pid)
 
       assert_received {:tls_alert, {:insufficient_security, _}}