diff --git a/Gemfile.lock b/Gemfile.lock
index 1ffd86486a53e..c5240e7e0a7d9 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -405,7 +405,7 @@ GEM
       nokogiri
     redcarpet (3.6.0)
     regexp_parser (2.9.2)
-    reline (0.5.10)
+    reline (0.5.11)
       io-console (~> 0.5)
     require_all (3.0.0)
     rex-arch (0.1.16)
diff --git a/lib/msf/base/sessions/command_shell.rb b/lib/msf/base/sessions/command_shell.rb
index bb9b04472aa74..d2a7bda503e66 100644
--- a/lib/msf/base/sessions/command_shell.rb
+++ b/lib/msf/base/sessions/command_shell.rb
@@ -547,7 +547,7 @@ def cmd_irb(*args)
     if expressions.empty?
       print_status('Starting IRB shell...')
       print_status("You are in the \"self\" (session) object\n")
-      framework.history_manager.with_context(name: :irb) do
+      framework.history_manager.with_context(name: :irb, input_library: :reline) do
         Rex::Ui::Text::IrbShell.new(self).run
       end
     else
@@ -586,7 +586,7 @@ def cmd_pry(*args)
     print_status('Starting Pry shell...')
     print_status("You are in the \"self\" (session) object\n")
     Pry.config.history_load = false
-    framework.history_manager.with_context(history_file: Msf::Config.pry_history, name: :pry) do
+    framework.history_manager.with_context(history_file: Msf::Config.pry_history, name: :pry, input_library: Pry.input) do
       self.pry
     end
   end
diff --git a/lib/msf/core/feature_manager.rb b/lib/msf/core/feature_manager.rb
index 872087c350493..c40944ccf301c 100644
--- a/lib/msf/core/feature_manager.rb
+++ b/lib/msf/core/feature_manager.rb
@@ -29,6 +29,7 @@ class FeatureManager
     LDAP_SESSION_TYPE = 'ldap_session_type'
     SHOW_SUCCESSFUL_LOGINS = 'show_successful_logins'
     DISPLAY_MODULE_ACTION = 'display_module_action'
+    USE_RELINE = 'use_reline'
 
     DEFAULTS = [
       {
@@ -132,6 +133,13 @@ class FeatureManager
         requires_restart: false,
         default_value: true,
         developer_notes: 'Added as a feature so users can turn it off if they wish to reduce clutter in their terminal'
+      }.freeze,
+      {
+        name: USE_RELINE,
+        description: 'When enabled, the new Reline library will be used instead of the legacy Readline library for input/output.',
+        requires_restart: true,
+        default_value: false,
+        developer_notes: 'To be enabled by default after sufficient testing and Reline fixes the issues raised here: https://github.com/ruby/reline/issues/created_by/sjanusz-r7'
       }.freeze
     ].freeze
 
diff --git a/lib/msf/ui/console/command_dispatcher/core.rb b/lib/msf/ui/console/command_dispatcher/core.rb
index 5599879afad6a..d7399ac6ee73b 100644
--- a/lib/msf/ui/console/command_dispatcher/core.rb
+++ b/lib/msf/ui/console/command_dispatcher/core.rb
@@ -760,7 +760,8 @@ def cmd_features_tabs(_str, words)
   end
 
   def cmd_history(*args)
-    length = Readline::HISTORY.length
+    history = Msf::Ui::Console::MsfReadline.instance.history
+    length = history.length
 
     if length < @history_limit
       limit = length
@@ -780,10 +781,10 @@ def cmd_history(*args)
           limit = val.to_i
         end
       when '-c'
-        if Readline::HISTORY.respond_to?(:clear)
-          Readline::HISTORY.clear
-        elsif defined?(RbReadline)
-          RbReadline.clear_history
+        if history.respond_to?(:clear)
+          history.clear
+        elsif history.respond_to?(:pop) && history.respond_to?(:length)
+          history.length.times { |_i| history.pop }
         else
           print_error('Could not clear history, skipping file')
           return false
@@ -808,7 +809,7 @@ def cmd_history(*args)
 
     (start..length-1).each do |pos|
       cmd_num = (pos + 1).to_s
-      print_line "#{cmd_num.ljust(pad_len)}  #{Readline::HISTORY[pos]}"
+      print_line "#{cmd_num.ljust(pad_len)}  #{history[pos]}"
     end
   end
 
diff --git a/lib/msf/ui/console/command_dispatcher/developer.rb b/lib/msf/ui/console/command_dispatcher/developer.rb
index 33c2c39a3f1f6..3fbc0c3e15fec 100644
--- a/lib/msf/ui/console/command_dispatcher/developer.rb
+++ b/lib/msf/ui/console/command_dispatcher/developer.rb
@@ -129,8 +129,15 @@ def cmd_irb(*args)
     if expressions.empty?
       print_status('Starting IRB shell...')
 
-      framework.history_manager.with_context(name: :irb) do
+      framework.history_manager.with_context(name: :irb, input_library: :reline) do
         begin
+          if Msf::Ui::Console::MsfReadline.instance.using_reline?
+            config = {}
+            config[:autocomplete] = Msf::Ui::Console::MsfReadline.instance.autocompletion
+            # IRB changes propagate out of the context of IRB. We store the current state and restore it on exit.
+            # TODO: Once IRB fixes this behaviour, we should be able to remove this patch.
+            config[:core] = Msf::Ui::Console::MsfReadline.instance.backend.core.dup
+          end
           if active_module
             print_status("You are in #{active_module.fullname}\n")
             Rex::Ui::Text::IrbShell.new(active_module).run
@@ -140,6 +147,11 @@ def cmd_irb(*args)
           end
         rescue
           print_error("Error during IRB: #{$!}\n\n#{$@.join("\n")}")
+        ensure
+          if Msf::Ui::Console::MsfReadline.instance.using_reline?
+            Msf::Ui::Console::MsfReadline.instance.backend.instance_variable_set(:@core, config[:core])
+            Msf::Ui::Console::MsfReadline.instance.autocompletion = config[:autocomplete]
+          end
         end
       end
 
@@ -192,7 +204,7 @@ def cmd_pry(*args)
     print_status('Starting Pry shell...')
 
     Pry.config.history_load = false
-    framework.history_manager.with_context(history_file: Msf::Config.pry_history, name: :pry) do
+    framework.history_manager.with_context(history_file: Msf::Config.pry_history, name: :pry, input_library: Pry.input) do
       if active_module
         print_status("You are in the \"#{active_module.fullname}\" module object\n")
         active_module.pry
@@ -515,6 +527,10 @@ def cmd_time_help
   private
 
   def modified_files
+    # Temporary work-around until Open3 gets fixed on Windows 11:
+    # https://github.com/ruby/open3/issues/9
+    return [] if Rex::Compat.is_cygwin || Rex::Compat.is_windows
+
     # Using an array avoids shelling out, so we avoid escaping/quoting
     changed_files = %w[git diff --name-only]
     begin
diff --git a/lib/msf/ui/console/command_dispatcher/session.rb b/lib/msf/ui/console/command_dispatcher/session.rb
index de791bdea29d7..9c59e7fc5b02a 100644
--- a/lib/msf/ui/console/command_dispatcher/session.rb
+++ b/lib/msf/ui/console/command_dispatcher/session.rb
@@ -96,7 +96,7 @@ def cmd_irb(*args)
             if expressions.empty?
               print_status('Starting IRB shell...')
               print_status("You are in the session object\n")
-              framework.history_manager.with_context(name: :irb) do
+              framework.history_manager.with_context(name: :irb, input_library: :reline) do
                 Rex::Ui::Text::IrbShell.new(session).run
               end
             else
@@ -136,7 +136,7 @@ def cmd_pry(*args)
             print_status("You are in the session object\n")
 
             Pry.config.history_load = false
-            session.framework.history_manager.with_context(history_file: Msf::Config.pry_history, name: :pry) do
+            session.framework.history_manager.with_context(history_file: Msf::Config.pry_history, name: :pry, input_library: Pry.input) do
               session.pry
             end
           end
diff --git a/lib/msf/ui/console/driver.rb b/lib/msf/ui/console/driver.rb
index bc42cb1a4cb99..f256fcb633192 100644
--- a/lib/msf/ui/console/driver.rb
+++ b/lib/msf/ui/console/driver.rb
@@ -313,12 +313,9 @@ def save_config
   # Saves the recent history to the specified file
   #
   def save_recent_history(path)
-    num = Readline::HISTORY.length - hist_last_saved - 1
-
-    tmprc = ""
-    num.times { |x|
-      tmprc << Readline::HISTORY[hist_last_saved + x] + "\n"
-    }
+    history = Msf::Ui::Console::MsfReadline.instance.history
+    num = history.length - hist_last_saved - 1
+    tmprc = history.entries[hist_last_saved..].join("\n")
 
     if tmprc.length > 0
       print_status("Saving last #{num} commands to #{path} ...")
@@ -329,7 +326,7 @@ def save_recent_history(path)
 
     # Always update this, even if we didn't save anything. We do this
     # so that we don't end up saving the "makerc" command itself.
-    self.hist_last_saved = Readline::HISTORY.length
+    self.hist_last_saved = history.length
   end
 
   #
diff --git a/lib/msf/ui/console/module_option_tab_completion.rb b/lib/msf/ui/console/module_option_tab_completion.rb
index f8ecd07216e3d..919a5caa7a832 100644
--- a/lib/msf/ui/console/module_option_tab_completion.rb
+++ b/lib/msf/ui/console/module_option_tab_completion.rb
@@ -53,18 +53,18 @@ def tab_complete_option(mod, str, words)
             option_name = str.chop
             option_value = ''
 
-            ::Readline.completion_append_character = ' '
+            Msf::Ui::Console::MsfReadline.instance.completion_append_character = ' '
             return tab_complete_option_values(mod, option_value, words, opt: option_name).map { |value| "#{str}#{value}" }
           elsif str.include?('=')
             str_split = str.split('=')
             option_name = str_split[0].strip
             option_value = str_split[1].strip
 
-            ::Readline.completion_append_character = ' '
+            Msf::Ui::Console::MsfReadline.instance.completion_append_character = ' '
             return tab_complete_option_values(mod, option_value, words, opt: option_name).map { |value| "#{option_name}=#{value}" }
           end
 
-          ::Readline.completion_append_character = ''
+          Msf::Ui::Console::MsfReadline.instance.completion_append_character = ''
           tab_complete_option_names(mod, str, words).map { |name| "#{name}=" }
         end
 
diff --git a/lib/msf/ui/console/msf_readline.rb b/lib/msf/ui/console/msf_readline.rb
new file mode 100644
index 0000000000000..520af9dff1712
--- /dev/null
+++ b/lib/msf/ui/console/msf_readline.rb
@@ -0,0 +1,117 @@
+#
+# This class is responsible for handling Readline/Reline-agnostic user input.
+#
+class Msf::Ui::Console::MsfReadline
+  require 'singleton'
+  # Required to check the Reline flag.
+  require 'msf/core/feature_manager'
+  require 'readline'
+  require 'reline'
+
+  include Singleton
+
+  attr_reader :history
+  # This is currently required for a Reline + IRB workaround, where changes made by IRB to the Reline Face and LineEditor
+  # persist after exiting IRB.
+  # TODO: We can remove this once IRB fixes the config escaping the IRB context
+  attr_reader :backend
+
+  def initialize
+    @backend = using_reline? ? ::Reline : ::Readline
+    @history = @backend::HISTORY
+  end
+
+  def method_missing(sym, *args, &block)
+    if @backend.respond_to?(sym)
+      @backend.send(sym, *args, &block)
+    else
+      msg = "Method '#{sym}' not found in #{@backend.class}"
+      elog(msg)
+      raise NoMethodError, msg
+    end
+  end
+
+  # Read a line from the user, and return it.
+  # @param prompt [String] The prompt to show to the user.
+  # @param add_history [Boolean] True if the user's input should be saved to the history.
+  # @param opts [Hash] Options
+  # @return String The line that the user has entered.
+  def readline(prompt, add_history = false, opts: {})
+    input(prompt, add_history, opts: opts)
+  end
+
+  def using_reline?
+    return @using_reline unless @using_reline.nil?
+
+    @using_reline = Msf::FeatureManager.instance.enabled?(Msf::FeatureManager::USE_RELINE)
+  end
+
+  private
+
+  attr_accessor :using_reline
+  attr_writer :backend
+
+  def input(*args, opts: {})
+    using_reline? ? input_reline(*args, opts: opts) : input_rbreadline(*args, opts: opts)
+  end
+
+  def input_rbreadline(prompt, add_history = false, opts: {})
+    # rb-readlines's Readline.readline hardcodes the input and output to
+    # $stdin and $stdout, which means setting `Readline.input` or
+    # `Readline.output` has no effect when running `Readline.readline` with
+    # rb-readline, so need to reimplement
+    # []`Readline.readline`](https://github.com/luislavena/rb-readline/blob/ce4908dae45dbcae90a6e42e3710b8c3a1f2cd64/lib/readline.rb#L36-L58)
+    # for rb-readline to support setting input and output.  Output needs to
+    # be set so that colorization works for the prompt on Windows.
+
+    input_on_entry = RbReadline.rl_instream
+    output_on_entry = RbReadline.rl_outstream
+
+    begin
+      RbReadline.rl_instream = opts[:fd]
+      RbReadline.rl_outstream = opts[:output]
+      line = RbReadline.readline(prompt.to_s)
+    rescue ::StandardError => e
+      RbReadline.rl_instream = input_on_entry
+      RbReadline.rl_outstream = output_on_entry
+      RbReadline.rl_cleanup_after_signal
+      RbReadline.rl_deprep_terminal
+
+      raise e
+    end
+
+    if add_history && line && !line.start_with?(' ')
+      # Don't add duplicate lines to history
+      if ::Readline::HISTORY.empty? || line.strip != ::Readline::HISTORY[-1]
+        RbReadline.add_history(line.strip)
+      end
+    end
+
+    line.dup
+  end
+
+  def input_reline(prompt, add_history = false, opts: {})
+    input_on_entry = Reline::IOGate.instance_variable_get(:@input)
+    output_on_entry = Reline::IOGate.instance_variable_get(:@output)
+
+    begin
+      input_external_encoding = opts[:fd].external_encoding
+      input_internal_encoding = opts[:fd].internal_encoding
+      opts[:fd].set_encoding(::Encoding::UTF_8)
+      Reline.input = opts[:fd]
+      Reline.output = opts[:output]
+      line = Reline.readline(prompt.to_s, add_history)
+    ensure
+      opts[:fd].set_encoding(input_external_encoding, input_internal_encoding)
+      Reline.input = input_on_entry
+      Reline.output = output_on_entry
+    end
+
+    # Don't add duplicate lines to history
+    if Reline::HISTORY.length > 1 && line == Reline::HISTORY[-2]
+      Reline::HISTORY.pop
+    end
+
+    line.dup
+  end
+end
diff --git a/lib/msf/ui/debug.rb b/lib/msf/ui/debug.rb
index 6bf8f8e3b1385..42067acff3457 100644
--- a/lib/msf/ui/debug.rb
+++ b/lib/msf/ui/debug.rb
@@ -220,13 +220,14 @@ def self.framework_config(framework)
       end
 
       def self.history(driver)
-        end_pos = Readline::HISTORY.length - 1
+        history = Msf::Ui::Console::MsfReadline.instance.history
+        end_pos = history.length - 1
         start_pos = end_pos - COMMAND_HISTORY_TOTAL > driver.hist_last_saved ? end_pos - (COMMAND_HISTORY_TOTAL - 1) : driver.hist_last_saved
 
         commands = ''
         while start_pos <= end_pos
           # Formats command position in history to 6 characters in length
-          commands += "#{'%-6.6s' % start_pos.to_s} #{Readline::HISTORY[start_pos]}\n"
+          commands += "#{'%-6.6s' % start_pos.to_s} #{history[start_pos]}\n"
           start_pos += 1
         end
 
diff --git a/lib/msf_autoload.rb b/lib/msf_autoload.rb
index c546aa8dc1957..83e652c183be9 100644
--- a/lib/msf_autoload.rb
+++ b/lib/msf_autoload.rb
@@ -347,3 +347,17 @@ def finalize_loader(loader)
 
 # XXX: Should be removed once the `lib/metasploit` folder is loaded by Zeitwerk
 require 'metasploit/framework/hashes'
+
+# TODO: Remove this monkey-patch once the following issue is addressed over on Reline's repository here:
+# https://github.com/ruby/reline/issues/756
+require 'reline'
+class ::Reline::Core
+  alias old_completion_append_character= completion_append_character=
+  alias old_completion_append_character completion_append_character
+
+  def completion_append_character=(v)
+    self.old_completion_append_character = v
+    # Additionally keep the line_editor in sync
+    line_editor.completion_append_character = self.old_completion_append_character
+  end
+end
diff --git a/lib/rex/post/meterpreter/ui/console/command_dispatcher/stdapi/fs.rb b/lib/rex/post/meterpreter/ui/console/command_dispatcher/stdapi/fs.rb
index 676be4ace17e8..8183175cc161f 100644
--- a/lib/rex/post/meterpreter/ui/console/command_dispatcher/stdapi/fs.rb
+++ b/lib/rex/post/meterpreter/ui/console/command_dispatcher/stdapi/fs.rb
@@ -902,7 +902,7 @@ def tab_complete_cdirectory(str, words)
 
   def tab_complete_path(str, words, dir_only)
     if client.platform == 'windows'
-        ::Readline.completion_case_fold = true
+      Msf::Ui::Console::MsfReadline.instance.completion_case_fold = true
     end
     if client.commands.include?(COMMAND_ID_STDAPI_FS_LS)
       expanded = str
@@ -915,7 +915,7 @@ def tab_complete_path(str, words, dir_only)
         # This is annoying if we're recursively tab-traversing our way through subdirectories -
         # we may want to continue traversing, but MSF will add a space, requiring us to back up to continue
         # tab-completing our way through successive subdirectories.
-        ::Readline.completion_append_character = nil
+        Msf::Ui::Console::MsfReadline.instance.completion_append_character = nil
       end
       results
     else
diff --git a/lib/rex/post/sql/ui/console/interactive_sql_client.rb b/lib/rex/post/sql/ui/console/interactive_sql_client.rb
index 75fc5c106f452..6a57bc7eaf19e 100644
--- a/lib/rex/post/sql/ui/console/interactive_sql_client.rb
+++ b/lib/rex/post/sql/ui/console/interactive_sql_client.rb
@@ -73,7 +73,7 @@ def _multiline_with_fallback
     return { status: :fail, errors: ["Unable to get history file for session type: #{name}"] } if history_file.nil?
 
     # Multiline (Reline) and fallback (Readline) have separate history contexts as they are two different libraries.
-    framework.history_manager.with_context(history_file: history_file , name: name, input_library: :reline) do
+    framework.history_manager.with_context(history_file: history_file, name: name, input_library: :reline) do
       query = _multiline
     end
 
diff --git a/lib/rex/ui/text/dispatcher_shell.rb b/lib/rex/ui/text/dispatcher_shell.rb
index 2131cc363292d..58c26c44fb51f 100644
--- a/lib/rex/ui/text/dispatcher_shell.rb
+++ b/lib/rex/ui/text/dispatcher_shell.rb
@@ -311,7 +311,7 @@ def tab_complete_directory(str, words)
         # This is annoying if we're recursively tab-traversing our way through subdirectories -
         # we may want to continue traversing, but MSF will add a space, requiring us to back up to continue
         # tab-completing our way through successive subdirectories.
-        ::Readline.completion_append_character = nil
+        Msf::Ui::Console::MsfReadline.instance.completion_append_character = nil
       end
 
       if dirs.length == 0 && File.directory?(str)
@@ -408,9 +408,13 @@ def initialize(prompt, prompt_char = '>', histfile = nil, framework = nil, name
   # a design problem in the Readline module and depends on the
   # Readline.basic_word_break_characters variable being set to \x00
   #
-  def tab_complete(str)
-    ::Readline.completion_append_character = ' '
-    ::Readline.completion_case_fold = false
+  def tab_complete(str, opts: {})
+    Msf::Ui::Console::MsfReadline.instance.completion_append_character = ' '
+    Msf::Ui::Console::MsfReadline.instance.completion_case_fold = false
+
+    if opts[:preposing] && Msf::Ui::Console::MsfReadline.instance.using_reline?
+      str = "#{opts[:preposing]}#{str}"
+    end
 
     # Check trailing whitespace so we can tell 'x' from 'x '
     str_match = str.match(/[^\\]([\\]{2})*\s+$/)
@@ -424,11 +428,7 @@ def tab_complete(str)
 
     # Pop the last word and pass it to the real method
     result = tab_complete_stub(str, split_str)
-    if result
-      result.uniq
-    else
-      result
-    end
+    result&.uniq
   end
 
   # Performs tab completion of a command, if supported
diff --git a/lib/rex/ui/text/input/readline.rb b/lib/rex/ui/text/input/readline.rb
index 85ca9d1218056..529a39e34e7ed 100644
--- a/lib/rex/ui/text/input/readline.rb
+++ b/lib/rex/ui/text/input/readline.rb
@@ -4,30 +4,32 @@ module Rex
 module Ui
 module Text
 
-begin
-
-  ###
   #
   # This class implements standard input using readline against
   # standard input.  It supports tab completion.
   #
-  ###
   class Input::Readline < Rex::Ui::Text::Input
 
     #
-    # Initializes the readline-aware Input instance for text.
+    # The prompt that is to be displayed.
     #
-    def initialize(tab_complete_proc = nil)
-      if(not Object.const_defined?('Readline'))
-        require 'readline'
-      end
+    attr_accessor :prompt
 
-      self.extend(::Readline)
+    #
+    # The output handle to use when displaying the prompt.
+    #
+    attr_accessor :output
 
+    #
+    # Initializes the readline-aware Input instance for text.
+    #
+    def initialize(tab_complete_proc = nil)
+      super()
       if tab_complete_proc
-        ::Readline.basic_word_break_characters = ""
-        @rl_saved_proc = with_error_handling(tab_complete_proc)
-        ::Readline.completion_proc = @rl_saved_proc
+        Msf::Ui::Console::MsfReadline.instance.basic_word_break_characters = ''
+        # Cache the value so that we can use it when resetting the proc.
+        @completion_proc = tab_complete_proc
+        Msf::Ui::Console::MsfReadline.instance.completion_proc = with_error_handling(@completion_proc)
       end
     end
 
@@ -35,24 +37,11 @@ def initialize(tab_complete_proc = nil)
     # Reattach the original completion proc
     #
     def reset_tab_completion(tab_complete_proc = nil)
-      ::Readline.basic_word_break_characters = "\x00"
-      ::Readline.completion_proc = tab_complete_proc ? with_error_handling(tab_complete_proc) : @rl_saved_proc
+      Msf::Ui::Console::MsfReadline.instance.basic_word_break_characters = "\x00"
+      @completion_proc = with_error_handling(tab_complete_proc) if tab_complete_proc
+      Msf::Ui::Console::MsfReadline.instance.completion_proc = @completion_proc
     end
 
-
-    #
-    # Retrieve the line buffer
-    #
-    def line_buffer
-      if defined? RbReadline
-        RbReadline.rl_line_buffer
-      else
-        ::Readline.line_buffer
-      end
-    end
-
-    attr_accessor :prompt
-
     #
     # Whether or not the input medium supports readline.
     #
@@ -95,11 +84,11 @@ def pgets
       begin
         Thread.current.priority = -20
 
-        output.prompting
-        line = readline_with_output(prompt, true)
-        ::Readline::HISTORY.pop if (line and line.empty?)
+        output.prompting(true)
+        line = Msf::Ui::Console::MsfReadline.instance.readline(prompt, true, opts: { fd: fd, output: output })
       ensure
         Thread.current.priority = orig || 0
+        output.prompting(false)
       end
 
       line
@@ -120,88 +109,21 @@ def intrinsic_shell?
       true
     end
 
-    #
-    # The prompt that is to be displayed.
-    #
-    attr_accessor :prompt
-    #
-    # The output handle to use when displaying the prompt.
-    #
-    attr_accessor :output
-
     private
 
-    def readline_with_output(prompt, add_history=false)
-      # rb-readlines's Readline.readline hardcodes the input and output to
-      # $stdin and $stdout, which means setting `Readline.input` or
-      # `Readline.ouput` has no effect when running `Readline.readline` with
-      # rb-readline, so need to reimplement
-      # []`Readline.readline`](https://github.com/luislavena/rb-readline/blob/ce4908dae45dbcae90a6e42e3710b8c3a1f2cd64/lib/readline.rb#L36-L58)
-      # for rb-readline to support setting input and output.  Output needs to
-      # be set so that colorization works for the prompt on Windows.
-      self.prompt = prompt
-
-      # TODO: there are unhandled quirks in async output buffering that
-      # we have not solved yet, for instance when loading meterpreter
-      # extensions, supporting Windows, printing output from commands, etc.
-      # Remove this guard when issues are resolved.
-=begin
-      reset_sequence = "\n\001\r\033[K\002"
-      if (/mingw/ =~ RUBY_PLATFORM)
-        reset_sequence = ""
-      end
-=end
-      reset_sequence = ""
-
-      if defined? RbReadline
-        RbReadline.rl_instream = fd
-        RbReadline.rl_outstream = output
-
-        begin
-          line = RbReadline.readline(reset_sequence + prompt)
-        rescue ::Exception => exception
-          RbReadline.rl_cleanup_after_signal()
-          RbReadline.rl_deprep_terminal()
-
-          raise exception
-        end
-
-        if add_history && line && !line.start_with?(' ')
-          # Don't add duplicate lines to history
-          if ::Readline::HISTORY.empty? || line.strip != ::Readline::HISTORY[-1]
-            RbReadline.add_history(line.strip)
-          end
-        end
-
-        line.try(:dup)
-      else
-        # The line that's read is immediately added to history
-        line = ::Readline.readline(reset_sequence + prompt, true)
-
-        # Don't add duplicate lines to history
-        if ::Readline::HISTORY.length > 1 && line == ::Readline::HISTORY[-2]
-          ::Readline::HISTORY.pop
-        end
-
-        line
-      end
-    end
-
-    private
+    attr_accessor :completion_proc
 
     def with_error_handling(proc)
       proc do |*args|
         proc.call(*args)
-      rescue StandardError => e
+      rescue ::StandardError => e
         elog("tab_complete_proc has failed with args #{args}", error: e)
         []
       end
     end
 
   end
-rescue LoadError
 end
 
 end
 end
-end
diff --git a/lib/rex/ui/text/irb_shell.rb b/lib/rex/ui/text/irb_shell.rb
index 49536041dcc53..20d2511bc7f86 100644
--- a/lib/rex/ui/text/irb_shell.rb
+++ b/lib/rex/ui/text/irb_shell.rb
@@ -28,6 +28,7 @@ def run
 
       IRB.setup(nil)
       IRB.conf[:PROMPT_MODE]  = :SIMPLE
+      IRB.conf[:USE_MULTILINE] = true
 
       @@IrbInitialized = true
     end
diff --git a/lib/rex/ui/text/output.rb b/lib/rex/ui/text/output.rb
index ef8f8fd030c6c..7877e81d61eaa 100644
--- a/lib/rex/ui/text/output.rb
+++ b/lib/rex/ui/text/output.rb
@@ -86,6 +86,11 @@ def puts(*args)
 
     nil
   end
+
+  # For Reline interop
+  def tty?
+    true
+  end
 end
 
 end
diff --git a/lib/rex/ui/text/output/stdio.rb b/lib/rex/ui/text/output/stdio.rb
index 085c912a60335..7d53fa0af8088 100644
--- a/lib/rex/ui/text/output/stdio.rb
+++ b/lib/rex/ui/text/output/stdio.rb
@@ -94,6 +94,7 @@ def print_raw(msg = '')
     msg
   end
   alias_method :write, :print_raw
+  alias_method :<<, :write
 
   def supports_color?
     case config[:color]
diff --git a/lib/rex/ui/text/output/tee.rb b/lib/rex/ui/text/output/tee.rb
index ebfbb4034a4b7..c729590ed05dc 100644
--- a/lib/rex/ui/text/output/tee.rb
+++ b/lib/rex/ui/text/output/tee.rb
@@ -44,6 +44,7 @@ def print_raw(msg = '')
   end
 
   alias :write :print_raw
+  alias_method :<<, :write
 
   def close
     self.fd.close if self.fd
diff --git a/lib/rex/ui/text/shell.rb b/lib/rex/ui/text/shell.rb
index 56a323c5bfacd..8cf0452ff6f09 100644
--- a/lib/rex/ui/text/shell.rb
+++ b/lib/rex/ui/text/shell.rb
@@ -63,10 +63,21 @@ def initialize(prompt, prompt_char = '>', histfile = nil, framework = nil, name
     self.framework = framework
   end
 
+  def create_tab_complete_proc
+    # Unless cont_flag because there's no tab complete for continuation lines
+    proc do |str, preposing = nil, postposting = nil|
+      next nil if cont_flag
+
+      result = tab_complete(str, opts: { preposing: preposing, postposting: postposting })
+      result.map! { |val| val[preposing.to_s.length..] } if result && Msf::Ui::Console::MsfReadline.instance.using_reline?
+
+      next result
+    end
+  end
+
   def init_tab_complete
     if (self.input and self.input.supports_readline)
-      # Unless cont_flag because there's no tab complete for continuation lines
-      self.input = Input::Readline.new(lambda { |str| tab_complete(str) unless cont_flag })
+      self.input = Input::Readline.new(create_tab_complete_proc)
       self.input.output = self.output
     end
   end
@@ -114,8 +125,8 @@ def unset_log_source
   #
   # Performs tab completion on the supplied string.
   #
-  def tab_complete(str)
-    return tab_complete_proc(str) if (tab_complete_proc)
+  def tab_complete(str, opts: {})
+    return tab_complete_proc(str, opts: opts) if (tab_complete_proc)
   end
 
   #
@@ -304,13 +315,13 @@ def with_history_manager_context
 
     begin
       history_manager.with_context(history_file: histfile, name: name) do
-        self.hist_last_saved = Readline::HISTORY.length
+        self.hist_last_saved = Msf::Ui::Console::MsfReadline.instance.history.length
 
         yield
       end
     ensure
       history_manager.flush
-      self.hist_last_saved = Readline::HISTORY.length
+      self.hist_last_saved = Msf::Ui::Console::MsfReadline.instance.history.length
     end
   end
 
diff --git a/lib/rex/ui/text/shell/history_manager.rb b/lib/rex/ui/text/shell/history_manager.rb
index cde3495fc9e8e..8dc07ae8b0ecd 100644
--- a/lib/rex/ui/text/shell/history_manager.rb
+++ b/lib/rex/ui/text/shell/history_manager.rb
@@ -1,6 +1,7 @@
 # -*- coding: binary -*-
 
-require 'singleton'
+require 'reline'
+require 'readline'
 
 module Rex
 module Ui
@@ -28,8 +29,10 @@ def initialize
   # @param [Proc] block
   # @return [nil]
   def with_context(history_file: nil, name: nil, input_library: nil, &block)
-    # Default to Readline for backwards compatibility.
-    push_context(history_file: history_file, name: name, input_library: input_library || :readline)
+    # Instead of defaulting to either Reline or Readline and potentially break the console when things get out of sync,
+    # use the single source of truth to determine what we should default to.
+    default_input_library = Msf::Ui::Console::MsfReadline.instance.using_reline? ? :reline : :readline
+    push_context(history_file: history_file, name: name, input_library: input_library || default_input_library)
 
     begin
       block.call
@@ -124,12 +127,7 @@ def readline_available?
   end
 
   def reline_available?
-    begin
-      require 'reline'
-      defined?(::Reline)
-    rescue ::LoadError => _e
-      false
-    end
+    defined?(::Reline)
   end
 
   def clear_readline
diff --git a/modules/post/linux/manage/pseudo_shell.rb b/modules/post/linux/manage/pseudo_shell.rb
index 6cdac56f8e230..2dbdb9a7ff3ae 100644
--- a/modules/post/linux/manage/pseudo_shell.rb
+++ b/modules/post/linux/manage/pseudo_shell.rb
@@ -4,6 +4,7 @@
 ##
 
 require 'readline'
+require 'reline'
 
 class MetasploitModule < Msf::Post
   include Msf::Post::File
@@ -104,9 +105,9 @@ def help
   def prompt_show
     promptshell = "#{@vusername}@#{@vhostname}:#{pwd.strip}#{@vpromptchar} "
     comp = proc { |s| LIST.grep(/^#{Regexp.escape(s)}/) }
-    Readline.completion_append_character = ' '
-    Readline.completion_proc = comp
-    input = Readline.readline(promptshell, true)
+    Msf::Ui::Console::MsfReadline.instance.completion_append_character = ' '
+    Msf::Ui::Console::MsfReadline.instance.completion_proc = comp
+    input = Msf::Ui::Console::MsfReadline.instance.readline(promptshell, true)
     return nil if input.nil?
 
     input
diff --git a/spec/lib/msf/debug_spec.rb b/spec/lib/msf/debug_spec.rb
index 82baa903f8bdd..ce7cd60899129 100644
--- a/spec/lib/msf/debug_spec.rb
+++ b/spec/lib/msf/debug_spec.rb
@@ -212,7 +212,7 @@
   end
 
   it 'correctly retrieves and parses a command history shorter than the command total' do
-    stub_const('Readline::HISTORY', Array.new(4) { |i| "Command #{i + 1}" })
+    allow(Msf::Ui::Console::MsfReadline.instance).to receive(:history).and_return(Array.new(4) { |i| "Command #{i + 1}" })
 
     driver = instance_double(
       Msf::Ui::Console::Driver,
@@ -251,7 +251,7 @@
 
     stub_const('Msf::Ui::Debug::COMMAND_HISTORY_TOTAL', 10)
 
-    stub_const('Readline::HISTORY', Array.new(10) { |i| "Command #{i + 1}" })
+    allow(Msf::Ui::Console::MsfReadline.instance).to receive(:history).and_return(Array.new(10) { |i| "Command #{i + 1}" })
 
     history_output = <<~E_LOG
       ##  %grnHistory%clr
@@ -288,7 +288,7 @@
     )
 
     stub_const('Msf::Ui::Debug::COMMAND_HISTORY_TOTAL', 10)
-    stub_const('Readline::HISTORY', Array.new(15) { |i| "Command #{i + 1}" })
+    allow(Msf::Ui::Console::MsfReadline.instance).to receive(:history).and_return(Array.new(15) { |i| "Command #{i + 1}" })
 
     history_output = <<~E_LOG
       ##  %grnHistory%clr
@@ -325,7 +325,7 @@
     )
 
     stub_const('Msf::Ui::Debug::COMMAND_HISTORY_TOTAL', 10)
-    stub_const('Readline::HISTORY', Array.new(15) { |i| "Command #{i + 1}" })
+    allow(Msf::Ui::Console::MsfReadline.instance).to receive(:history).and_return(Array.new(15) { |i| "Command #{i + 1}" })
 
     history_output = <<~E_LOG
       ##  %grnHistory%clr
diff --git a/spec/lib/msf/ui/console/command_dispatcher/core_spec.rb b/spec/lib/msf/ui/console/command_dispatcher/core_spec.rb
index 79de59e7c79fb..f0088811f4c7b 100644
--- a/spec/lib/msf/ui/console/command_dispatcher/core_spec.rb
+++ b/spec/lib/msf/ui/console/command_dispatcher/core_spec.rb
@@ -1,6 +1,7 @@
 require 'spec_helper'
 
 require 'readline'
+require 'reline'
 
 RSpec.describe Msf::Ui::Console::CommandDispatcher::Core do
   include_context 'Msf::DBManager'
diff --git a/spec/lib/msf/ui/text/dispatcher_shell_spec.rb b/spec/lib/msf/ui/text/dispatcher_shell_spec.rb
index a9dbea33842d4..15941b04f67e0 100644
--- a/spec/lib/msf/ui/text/dispatcher_shell_spec.rb
+++ b/spec/lib/msf/ui/text/dispatcher_shell_spec.rb
@@ -1,5 +1,6 @@
 require 'spec_helper'
 require 'readline'
+require 'reline'
 
 RSpec.describe Rex::Ui::Text::DispatcherShell do
   let(:prompt) { '%undmsf6%clr' }
diff --git a/tools/exploit/metasm_shell.rb b/tools/exploit/metasm_shell.rb
index b2b24234083cf..68a5b22adad9b 100755
--- a/tools/exploit/metasm_shell.rb
+++ b/tools/exploit/metasm_shell.rb
@@ -31,7 +31,6 @@
 $:.unshift(ENV['MSF_LOCAL_LIB']) if ENV['MSF_LOCAL_LIB']
 
 require 'rex'
-require 'readline'
 require 'metasm'
 
 #PowerPC, seems broken for now in metasm
diff --git a/tools/exploit/nasm_shell.rb b/tools/exploit/nasm_shell.rb
index 9915274b37d1f..c60543c2a2322 100755
--- a/tools/exploit/nasm_shell.rb
+++ b/tools/exploit/nasm_shell.rb
@@ -21,7 +21,6 @@
 
 require 'msfenv'
 require 'rex'
-require 'readline'
 
 # Check to make sure nasm is installed and reachable through the user's PATH.
 begin