diff --git a/lib/msf/base/sessions/meterpreter_options.rb b/lib/msf/base/sessions/meterpreter_options.rb
index 2a7f149d64..b4b8dcedf5 100644
--- a/lib/msf/base/sessions/meterpreter_options.rb
+++ b/lib/msf/base/sessions/meterpreter_options.rb
@@ -75,6 +75,10 @@ module Msf
               'MeterpreterDebugBuild',
               [false, 'Use a debug version of Meterpreter']
             ),
+            OptMeterpreterDebugLogging.new(
+              'MeterpreterDebugLogging',
+              [false, 'The Meterpreter debug logging configuration, see https://github.com/rapid7/metasploit-framework/wiki/Meterpreter-Debugging-Meterpreter-Sessions']
+            )
           ],
           self.class
         )
diff --git a/lib/msf/core/opt_meterpreter_debug_logging.rb b/lib/msf/core/opt_meterpreter_debug_logging.rb
new file mode 100644
index 0000000000..e94c31d734
--- /dev/null
+++ b/lib/msf/core/opt_meterpreter_debug_logging.rb
@@ -0,0 +1,69 @@
+# -*- coding: binary -*-
+
+module Msf
+  ###
+  #
+  # Meterpreter Debug Logging option
+  #
+  ###
+  class OptMeterpreterDebugLogging < OptBase
+    def initialize(in_name, attrs = [], **kwargs)
+      super
+    end
+
+    def type
+      'meterpreterdebuglogging'
+    end
+
+    def validate_on_assignment?
+      true
+    end
+
+    def valid?(value, check_empty: true)
+      return false if !super(value, check_empty: check_empty)
+
+      begin
+        _parse_result = self.class.parse_logging_options(value)
+        true
+      rescue ::ArgumentError
+        false
+      end
+    end
+
+    ##
+    #
+    # Parses the given Meterpreter Debug Logging string
+    #
+    ##
+    def self.parse_logging_options(value)
+      result = {}
+      errors = []
+
+      return result if value.nil?
+
+      value = value.strip
+      # Match 'rpath:./file', 'rpath:/file', and drive letters e.g. 'rpath:C:/file'
+      rpath_regex = %r{^rpath:((\.?/\p{ASCII}+)|(\p{ASCII}:/\p{ASCII}+))}i
+
+      # Check if we log to rpath
+      if value.match?(rpath_regex)
+        # https://docs.microsoft.com/en-us/windows/win32/fileio/maximum-file-path-limitation?tabs=cmd
+        max_length = 260
+        rpath_value = value.split('rpath:').last
+        if rpath_value.length <= max_length
+          result[:rpath] = rpath_value
+        else
+          errors << "Rpath is too long. Max length: #{max_length}"
+        end
+      else
+        errors << 'Value is not a valid rpath string'
+      end
+
+      if errors.any?
+        raise ::ArgumentError, "Failed to validate MeterpreterDebugLogging option: #{value} with error/errors: #{errors.join('. ')}"
+      end
+
+      result
+    end
+  end
+end
diff --git a/lib/msf/core/payload/python/meterpreter_loader.rb b/lib/msf/core/payload/python/meterpreter_loader.rb
index dbc5f079df..d301b0b1bb 100644
--- a/lib/msf/core/payload/python/meterpreter_loader.rb
+++ b/lib/msf/core/payload/python/meterpreter_loader.rb
@@ -34,9 +34,10 @@ module Payload::Python::MeterpreterLoader
           default: true
         ),
         OptBool.new(
-          'PythonMeterpreterDebug',
-          'Enable debugging for the Python meterpreter'
-        ),
+          'MeterpreterDebugBuild',
+          'Enable debugging for the Python meterpreter',
+          aliases: ['PythonMeterpreterDebug']
+        )
       ] +
       Msf::Opt::http_header_options
     )
@@ -70,12 +71,16 @@ module Payload::Python::MeterpreterLoader
       txt.gsub('\\', '\\' * 8).gsub('\'', %q(\\\\\\\'))
     }
 
+    if ds['MeterpreterDebugBuild']
+      met.sub!(%q|DEBUGGING = False|, %q|DEBUGGING = True|)
+
+      logging_options = Msf::OptMeterpreterDebugLogging.parse_logging_options(ds['MeterpreterDebugLogging'])
+      met.sub!(%q|DEBUGGING_LOG_FILE_PATH = None|, %Q|DEBUGGING_LOG_FILE_PATH = "#{logging_options[:rpath]}"|) if logging_options[:rpath]
+    end
+
     unless ds['MeterpreterTryToFork']
       met.sub!('TRY_TO_FORK = True', 'TRY_TO_FORK = False')
     end
-    if ds['PythonMeterpreterDebug']
-      met.sub!('DEBUGGING = False', 'DEBUGGING = True')
-    end
 
     met.sub!("# PATCH-SETUP-ENCRYPTION #", python_encryptor_loader)
 
@@ -357,7 +362,6 @@ class AESCBC(object):
 		return _b2s(pt)
 ?
   end
-
 end
 
 end
diff --git a/spec/lib/msf/core/opt_meterpreter_debug_logging_spec.rb b/spec/lib/msf/core/opt_meterpreter_debug_logging_spec.rb
new file mode 100644
index 0000000000..3d05320991
--- /dev/null
+++ b/spec/lib/msf/core/opt_meterpreter_debug_logging_spec.rb
@@ -0,0 +1,20 @@
+# -*- coding:binary -*-
+
+require 'spec_helper'
+
+RSpec.describe Msf::OptMeterpreterDebugLogging do
+  valid_values = [
+    { value: 'rpath:C:/log.txt', normalized: 'rpath:C:/log.txt' },
+    { value: 'rpath:/tmp/log.txt', normalized: 'rpath:/tmp/log.txt' },
+    { value: 'rpath:./log.log', normalized: 'rpath:./log.log' },
+    { value: ' rpath:./log.log ', normalized: ' rpath:./log.log ' }
+  ]
+  invalid_values = [
+    { value: 'rpath', normalized: 'rpath' },
+    { value: 'C:', normalized: 'C:' },
+    { value: 'C', normalized: 'C' },
+    { value: 'rpath:C', normalized: 'rpath:C' }
+  ]
+
+  it_behaves_like 'an option', valid_values, invalid_values, 'meterpreterdebuglogging'
+end