diff --git a/monkey/infection_monkey/transport/http.py b/monkey/infection_monkey/transport/http.py
index ade37b31d..20b481f31 100644
--- a/monkey/infection_monkey/transport/http.py
+++ b/monkey/infection_monkey/transport/http.py
@@ -118,13 +118,20 @@ class HTTPConnectProxyHandler(http.server.BaseHTTPRequestHandler):
             post_data = self.rfile.read(content_length).decode()
             LOG.info("Received bootloader's request: {}".format(post_data))
             try:
-                r = requests.post(url=self.path, data=post_data, proxies=infection_monkey.control.ControlClient.proxies)
+                dest_path = self.path
+                r = requests.post(url=dest_path,
+                                  data=post_data,
+                                  verify=False,
+                                  proxies=infection_monkey.control.ControlClient.proxies)
+                self.send_response(r.status_code)
             except requests.exceptions.ConnectionError as e:
                 LOG.error("Couldn't forward request to the island: {}".format(e))
-                return self.send_response(404)
-            self.send_response(r.status_code)
-            self.end_headers()
-            self.wfile.write(r.content)
+                self.send_response(404)
+            except Exception as e:
+                LOG.error("Failed to forward bootloader request: {}".format(e))
+            finally:
+                self.end_headers()
+                self.wfile.write(r.content)
         except Exception as e:
             LOG.error("Failed receiving bootloader telemetry: {}".format(e))
 
diff --git a/monkey/monkey_island/cc/bootloader_server.py b/monkey/monkey_island/cc/bootloader_server.py
index a8fdda498..5adfb3d22 100644
--- a/monkey/monkey_island/cc/bootloader_server.py
+++ b/monkey/monkey_island/cc/bootloader_server.py
@@ -7,10 +7,13 @@ import logging
 import requests
 import pymongo
 
+from monkey_island.cc.environment import Environment
+
 # Disable "unverified certificate" warnings when sending requests to island
 urllib3.disable_warnings(urllib3.exceptions.InsecureRequestWarning)
 logger = logging.getLogger(__name__)
 
+
 class BootloaderHttpServer(ThreadingMixIn, HTTPServer):
 
     def __init__(self, mongo_url):
@@ -24,10 +27,7 @@ class BootloaderHTTPRequestHandler(BaseHTTPRequestHandler):
     def do_POST(self):
         content_length = int(self.headers['Content-Length'])
         post_data = self.rfile.read(content_length).decode()
-        conf = self.server.mongo_client['monkeyisland']['config'].find_one({'name': 'newconfig'})
-        if not conf:
-            conf = self.server.mongo_client['monkeyisland']['config'].find_one({'name': 'initial'})
-        island_server_path = BootloaderHTTPRequestHandler.get_bootloader_resource_path_from_config(conf)
+        island_server_path = BootloaderHTTPRequestHandler.get_bootloader_resource_url(self.request.getsockname()[0])
         island_server_path = parse.urljoin(island_server_path, self.path[1:])
         r = requests.post(url=island_server_path, data=post_data, verify=False)
 
@@ -44,6 +44,6 @@ class BootloaderHTTPRequestHandler(BaseHTTPRequestHandler):
             self.connection.close()
 
     @staticmethod
-    def get_bootloader_resource_path_from_config(config):
-        address = config['cnc']['servers']['current_server']
-        return parse.urljoin("https://"+address, "api/bootloader/")
+    def get_bootloader_resource_url(server_ip):
+        return "https://" + server_ip + ":" + str(Environment._ISLAND_PORT) + "/api/bootloader/"
+