This project seems dead for years. I have created a fork of this project with some major fixes. You can contribute to it here☺️: https://github.com/7Ragnarok7/Windows-Exploit-Suggester

README.md

@@ -39,9 +39,10 @@ $ ./windows-exploit-suggester.py --update
 ```
 install dependencies
 
-(install python-xlrd, $ pip install xlrd --upgrade)
+(install python-xlrd, $ python2 -m pip install xlrd --upgrade)
+
+Either run this from a Windows OS or feed it "systeminfo" as input, and point it to the microsoft database
 
-feed it "systeminfo" input, and point it to the microsoft database
 ```
 $ ./windows-exploit-suggester.py --database 2014-06-06-mssb.xlsx --systeminfo win7sp1-systeminfo.txt 
 [*] initiating...

windows-exploit-suggester.py

@@ -1,4 +1,4 @@
-#!/usr/bin/env python
+#!/usr/bin/env python2
 # -*- coding: utf-8 -*-
 #
 # Windows Exploit Suggester
@@ -49,7 +49,7 @@
 #
 # install dependencies
 #
-# (install python-xlrd, $ pip install xlrd --upgrade)
+# (install python-xlrd, $ python2 -m pip install xlrd --upgrade)
 #
 # feed it "systeminfo" input, and point it to the microsoft database
 #
@@ -97,7 +97,7 @@
 # TROUBLESHOOTING
 #
 # If you're receiving the following error message, update the xlrd library
-# $ pip install xlrd --update
+# $ python2 -m pip install xlrd --update
 #
 # [*] initiating winsploit version 24...
 # [*] database file detected as xls or xlsx based on extension
@@ -964,6 +964,8 @@ def getname(ostext):
                [" 7","7"],
                [" 8","8"],
                ["2012","2012"],
+	       ["2016","2016"],
+	       ["2019","2019"],
                ["8.1","8.1"],
                [" 10","10"]]
 
@@ -1040,7 +1042,19 @@ def getarchitecture(ostext):
   if getname(ostext) == "2012" and architecture == "32":
     if ARGS.verbose:
       ALERT("forcing unidentified architecture to 64-bit because OS identified as Windows Server 2012 does not support 32-bit")
-    architecture = "64"  
+    architecture = "64"
+
+  # windows server 2016 is only 64-bit arch
+  if getname(ostext) == "2016" and architecture == "32":
+    if ARGS.verbose:
+      ALERT("forcing unidentified architecture to 64-bit because OS identified as Windows Server 2016 does not support 32-bit")
+    architecture = "64" 
+
+  # windows server 2019 is only 64-bit arch
+  if getname(ostext) == "2019" and architecture == "32":
+    if ARGS.verbose:
+      ALERT("forcing unidentified architecture to 64-bit because OS identified as Windows Server 2019 does not support 32-bit")
+    architecture = "64" 
 
   return architecture