diff --git a/monkey/infection_monkey/transport/http.py b/monkey/infection_monkey/transport/http.py
index 8745e62eb..efb39a71c 100644
--- a/monkey/infection_monkey/transport/http.py
+++ b/monkey/infection_monkey/transport/http.py
@@ -115,8 +115,12 @@ class HTTPConnectProxyHandler(http.server.BaseHTTPRequestHandler):
     def do_POST(self):
         content_length = int(self.headers['Content-Length'])  # <--- Gets the size of data
         post_data = self.rfile.read(content_length).decode()  # <--- Gets the data itself
-        r = requests.post(url=self.path, data=post_data)
-        if (r.status_code != 200):
+        try:
+            r = requests.post(url=self.path, data=post_data)
+        except requests.exceptions.ConnectionError as e:
+            LOG.error("Couldn't forward request to the island: {}".format(e))
+            return self.send_response(404)
+        if r.status_code != 200:
             # somehow forward post request to the next proxy
             r = requests.post(url=self.path, data=post_data, proxy=self.path)
             if (r.status_code != 200):
diff --git a/monkey/monkey_island/cc/app.py b/monkey/monkey_island/cc/app.py
index 4698d6007..80d743209 100644
--- a/monkey/monkey_island/cc/app.py
+++ b/monkey/monkey_island/cc/app.py
@@ -87,7 +87,7 @@ def init_app_url_rules(app):
 def init_api_resources(api):
     api.add_resource(Root, '/api')
     api.add_resource(Monkey, '/api/monkey', '/api/monkey/', '/api/monkey/<string:guid>')
-    api.add_resource(Bootloader, '/api/bootloader')
+    api.add_resource(Bootloader, '/api/bootloader/<string:os>')
     api.add_resource(LocalRun, '/api/local-monkey', '/api/local-monkey/')
     api.add_resource(ClientRun, '/api/client-monkey', '/api/client-monkey/')
     api.add_resource(Telemetry, '/api/telemetry', '/api/telemetry/', '/api/telemetry/<string:monkey_guid>')
diff --git a/monkey/monkey_island/cc/bootloader_server.py b/monkey/monkey_island/cc/bootloader_server.py
index 7706817f8..3ba15b5e2 100644
--- a/monkey/monkey_island/cc/bootloader_server.py
+++ b/monkey/monkey_island/cc/bootloader_server.py
@@ -1,4 +1,5 @@
 from http.server import HTTPServer, BaseHTTPRequestHandler
+from socketserver import ThreadingMixIn
 from urllib import parse
 import urllib3
 
@@ -9,7 +10,7 @@ import pymongo
 urllib3.disable_warnings(urllib3.exceptions.InsecureRequestWarning)
 
 
-class BootloaderHttpServer(HTTPServer):
+class BootloaderHttpServer(ThreadingMixIn, HTTPServer):
 
     def __init__(self, mongo_url):
         self.mongo_client = pymongo.MongoClient(mongo_url)
@@ -26,6 +27,7 @@ class BootloaderHTTPRequestHandler(BaseHTTPRequestHandler):
         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 = parse.urljoin(island_server_path, self.path)
         r = requests.post(url=island_server_path, data=post_data, verify=False)
 
         if r.status_code != 200:
diff --git a/monkey/monkey_island/cc/resources/bootloader.py b/monkey/monkey_island/cc/resources/bootloader.py
index 1094b139b..66eb48ae1 100644
--- a/monkey/monkey_island/cc/resources/bootloader.py
+++ b/monkey/monkey_island/cc/resources/bootloader.py
@@ -10,18 +10,29 @@ from monkey_island.cc.services.bootloader import BootloaderService
 class Bootloader(flask_restful.Resource):
 
     # Used by monkey. can't secure.
-    def post(self, **kw):
-        data = Bootloader.parse_bootloader_request(request.data)
+    def post(self, os):
+        if os == 'linux':
+            data = Bootloader.parse_bootloader_request_linux(request.data)
+        elif os == 'windows':
+            data = Bootloader.parse_bootloader_request_windows(request.data)
+        else:
+            return make_response({"status": "OS_NOT_FOUND"}, 404)
+
         resp = BootloaderService.parse_bootloader_data(data)
+
         if resp:
             return make_response({"status": "RUN"}, 200)
         else:
             return make_response({"status": "ABORT"}, 200)
 
     @staticmethod
-    def parse_bootloader_request(request_data: bytes) -> Dict[str, str]:
+    def parse_bootloader_request_linux(request_data: bytes) -> Dict[str, str]:
         parsed_data = json.loads(request_data.decode().replace("\n", "")
                                                       .replace("NAME=\"", "")
                                                       .replace("\"\"", "\"")
                                                       .replace("\":\",", "\":\"\","))
         return parsed_data
+
+    @staticmethod
+    def parse_bootloader_request_windows(request_data: bytes) -> Dict[str, str]:
+        return json.loads(request_data.decode("utf-16", "ignore"))