diff --git a/chaos_monkey/exploit/tools.py b/chaos_monkey/exploit/tools.py
index 1fc76147a..60e3950a6 100644
--- a/chaos_monkey/exploit/tools.py
+++ b/chaos_monkey/exploit/tools.py
@@ -389,7 +389,9 @@ class HTTPTools(object):
 
 def get_interface_to_target(dst):
     if sys.platform == "win32":
-        return get_close_matches(dst, local_ips())[0]
+        ips = local_ips()
+        matches = get_close_matches(dst, ips)
+        return matches[0] if (len(matches) > 0) else ips[0]
     else:
         # based on scapy implementation