diff --git a/monkey/infection_monkey/exploit/tools/http_tools.py b/monkey/infection_monkey/exploit/tools/http_tools.py
index 92696a5b7..5b73251d9 100644
--- a/monkey/infection_monkey/exploit/tools/http_tools.py
+++ b/monkey/infection_monkey/exploit/tools/http_tools.py
@@ -57,6 +57,6 @@ class HTTPTools(object):
         httpd.start()
         lock.acquire()
         return (
-            "http://%s:%s/%s" % (local_ip, local_port, urllib.parse.quote(host.os["type"])),
+            "http://%s:%s/%s" % (local_ip, local_port, urllib.parse.quote(host.os["type"].value)),
             httpd,
         )
diff --git a/monkey/infection_monkey/transport/http.py b/monkey/infection_monkey/transport/http.py
index 63aaa0b36..7bcbcd87d 100644
--- a/monkey/infection_monkey/transport/http.py
+++ b/monkey/infection_monkey/transport/http.py
@@ -62,7 +62,7 @@ class FileServHTTPRequestHandler(http.server.BaseHTTPRequestHandler):
             f.close()
 
     def send_head(self):
-        if self.path != "/" + urllib.parse.quote(self.victim_os):
+        if self.path != "/" + urllib.parse.quote(self.victim_os.value):
             self.send_error(500, "")
             return None, 0, 0
         try: