diff --git a/monkey/infection_monkey/monkey.py b/monkey/infection_monkey/monkey.py
index 7769ceab8..b3410704c 100644
--- a/monkey/infection_monkey/monkey.py
+++ b/monkey/infection_monkey/monkey.py
@@ -179,8 +179,11 @@ class InfectionMonkey(object):
                 if monkey_tunnel:
                     monkey_tunnel.set_tunnel_for_host(machine)
                 if self._default_server:
-                    machine.set_default_server(get_interface_to_target(machine.ip_addr) +
-                                               (':'+self._default_server_port if self._default_server_port else ''))
+                    if self._network.on_island(self._default_server):
+                        machine.set_default_server(get_interface_to_target(machine.ip_addr) +
+                                                   (':'+self._default_server_port if self._default_server_port else ''))
+                    else:
+                        machine.set_default_server(self._default_server)
                     LOG.debug("Default server: %s set to machine: %r" % (self._default_server, machine))
 
                 # Order exploits according to their type
diff --git a/monkey/infection_monkey/network/network_scanner.py b/monkey/infection_monkey/network/network_scanner.py
index 5f65e4228..837add48a 100644
--- a/monkey/infection_monkey/network/network_scanner.py
+++ b/monkey/infection_monkey/network/network_scanner.py
@@ -118,3 +118,6 @@ class NetworkScanner(object):
             if NetworkRange.get_range_obj(subnet_str).is_in_range(ip_address):
                 return True
         return False
+
+    def on_island(self, server):
+        return bool([x for x in self._ip_addresses if x in server])