diff --git a/lib/msf/base/serializer/readable_text.rb b/lib/msf/base/serializer/readable_text.rb
index 26caf1b2f3a37..7b1d452eab6c2 100644
--- a/lib/msf/base/serializer/readable_text.rb
+++ b/lib/msf/base/serializer/readable_text.rb
@@ -569,53 +569,18 @@ def self.dump_generic_module(mod, indent = '')
   # @param missing [Boolean] dump only empty required options.
   # @return [String] the string form of the information.
   def self.dump_options(mod, indent = '', missing = false)
-    options = mod.options.map { |_name, option| option }
-    options_grouped_by_conditions = options.group_by(&:conditions)
+    all_options = mod.options.map { |_name, option| option }
+
+    conditional_options, option_groups = all_options.partition { |option| option.group.nil? }
+    options_grouped_by_conditions = conditional_options.group_by(&:conditions)
+    options_by_group = option_groups.group_by { |option| option.group if mod.options.keys.include?(option.name) }
 
     options_with_conditions = ''.dup
     options_without_conditions = ''.dup
+    options_group = ''.dup
 
     options_grouped_by_conditions.each do |conditions, options|
-      tbl = Rex::Text::Table.new(
-        'Indent' => indent.length,
-        'Columns' =>
-          [
-            'Name',
-            'Current Setting',
-            'Required',
-            'Description'
-          ])
-
-      options.sort_by(&:name).each do |opt|
-        name = opt.name
-        if mod.datastore.is_a?(Msf::DataStoreWithFallbacks)
-          val = mod.datastore[name]
-        else
-          val = mod.datastore[name].nil? ? opt.default : mod.datastore[name]
-        end
-
-        next if (opt.advanced?)
-        next if (opt.evasion?)
-        next if (missing && opt.valid?(val))
-
-        desc = opt.desc.dup
-
-        # Hint at RPORT proto by regexing mixins
-        if name == 'RPORT' && opt.kind_of?(Msf::OptPort)
-          mod.class.included_modules.each do |m|
-            case m.name
-            when /tcp/i, /HttpClient$/
-              desc << ' (TCP)'
-              break
-            when /udp/i
-              desc << ' (UDP)'
-              break
-            end
-          end
-        end
-
-        tbl << [ name, opt.display_value(val), opt.required? ? "yes" : "no", desc ]
-      end
+      tbl = options_table(missing, mod, options, indent)
 
       next if conditions.any? && tbl.rows.empty?
 
@@ -627,10 +592,59 @@ def self.dump_options(mod, indent = '', missing = false)
       end
     end
 
-    result = "#{options_without_conditions}#{options_with_conditions}"
+    options_by_group.each do |group, options|
+      tbl = options_table(missing, mod, options, indent)
+      options_group << "\n\n#{indent}#{group.description}:\n\n"
+      options_group << tbl.to_s
+    end
+
+    result = "#{options_without_conditions}#{options_with_conditions}#{options_group}"
     result
   end
 
+  def self.options_table(missing, mod, options, indent)
+    tbl = Rex::Text::Table.new(
+      'Indent' => indent.length,
+      'Columns' =>
+        [
+          'Name',
+          'Current Setting',
+          'Required',
+          'Description'
+        ])
+    options.sort_by(&:name).each do |opt|
+      # Skip over advanced or evasion options
+      next if (opt.advanced? || opt.evasion?)
+
+      name = opt.name
+      if mod.datastore.is_a?(Msf::DataStoreWithFallbacks)
+        val = mod.datastore[name]
+      else
+        val = mod.datastore[name].nil? ? opt.default : mod.datastore[name]
+      end
+      next if (missing && opt.valid?(val))
+
+      desc = opt.desc.dup
+
+      # Hint at RPORT proto by regexing mixins
+      if name == 'RPORT' && opt.kind_of?(Msf::OptPort)
+        mod.class.included_modules.each do |m|
+          case m.name
+          when /tcp/i, /HttpClient$/
+            desc << ' (TCP)'
+            break
+          when /udp/i
+            desc << ' (UDP)'
+            break
+          end
+        end
+      end
+
+      tbl << [name, opt.display_value(val), opt.required? ? "yes" : "no", desc]
+    end
+    tbl
+  end
+
   # Dumps the advanced options associated with the supplied module.
   #
   # @param mod [Msf::Module] the module.
diff --git a/lib/msf/core/opt.rb b/lib/msf/core/opt.rb
index 964e6dbcc5f57..bf3731721ea0c 100644
--- a/lib/msf/core/opt.rb
+++ b/lib/msf/core/opt.rb
@@ -44,8 +44,8 @@ def self.RHOSTS(default= nil, required=true, desc="The target host(s), see https
       Msf::OptRhosts.new('RHOSTS', [ required, desc, default ], aliases: [ 'RHOST' ])
     end
 
-    def self.RHOST(default=nil, required=true, desc="The target host(s), see https://docs.metasploit.com/docs/using-metasploit/basics/using-metasploit.html")
-      Msf::OptRhosts.new('RHOSTS', [ required, desc, default ], aliases: [ 'RHOST' ])
+    def self.RHOST(default=nil, required=true, desc="The target host(s), see https://docs.metasploit.com/docs/using-metasploit/basics/using-metasploit.html", **kwargs)
+      Msf::OptRhosts.new('RHOSTS', [ required, desc, default ], aliases: [ 'RHOST' ], **kwargs)
     end
 
     # @return [OptPort]
diff --git a/lib/msf/core/opt_base.rb b/lib/msf/core/opt_base.rb
index dccda5031d8bf..fb302a404c994 100644
--- a/lib/msf/core/opt_base.rb
+++ b/lib/msf/core/opt_base.rb
@@ -26,7 +26,7 @@ class OptBase
     #
     def initialize(in_name, attrs = [],
                    required: false, desc: nil, default: nil, conditions: [], enums: [], regex: nil, aliases: [], max_length: nil,
-                   fallbacks: [])
+                   fallbacks: [], group: nil)
       self.name     = in_name
       self.advanced = false
       self.evasion  = false
@@ -34,6 +34,7 @@ def initialize(in_name, attrs = [],
       self.max_length = max_length
       self.conditions = conditions
       self.fallbacks = fallbacks
+      self.group = group
 
       if attrs.is_a?(String) || attrs.length == 0
         self.required = required
@@ -230,6 +231,9 @@ def invalid_value_length?(value)
     #
     attr_accessor :max_length
 
+    # @return [Msf::OptionGroup, nil] The option group that this option belongs to if any
+    attr_accessor :group
+
     protected
 
     attr_writer   :required, :desc, :default # :nodoc:
diff --git a/lib/msf/core/opt_condition.rb b/lib/msf/core/opt_condition.rb
index fcfd2744a176a..bb189031b383a 100644
--- a/lib/msf/core/opt_condition.rb
+++ b/lib/msf/core/opt_condition.rb
@@ -3,9 +3,10 @@
 module Msf
   module OptCondition
     # Check a condition's result
-    # @param [Msf::Module] mod The module module
-    # @param [Msf::OptBase] opt the option which has conditions present
-    # @return [String]
+    # @param [String] left_value The left hand side of the condition
+    # @param [String] operator The conditions comparison operator
+    # @param [String] right_value The right hand side of the condition
+    # @return [Boolean]
     def self.eval_condition(left_value, operator, right_value)
       case operator.to_sym
       when :==
@@ -16,6 +17,8 @@ def self.eval_condition(left_value, operator, right_value)
         right_value.include?(left_value)
       when :nin
         !right_value.include?(left_value)
+      else
+        raise ArgumentError("Operator: #{operator} is invalid")
       end
     end
 
diff --git a/lib/msf/core/option_group.rb b/lib/msf/core/option_group.rb
new file mode 100644
index 0000000000000..9dd3628a26a5d
--- /dev/null
+++ b/lib/msf/core/option_group.rb
@@ -0,0 +1,13 @@
+# -*- coding: binary -*-
+
+module Msf
+  class OptionGroup
+
+    attr_accessor :name, :description
+
+    def initialize(name:, description:)
+      self.name = name
+      self.description = description
+    end
+  end
+end
diff --git a/lib/msf/core/optional_session.rb b/lib/msf/core/optional_session.rb
index 92080142fb6d7..93903b25fa58b 100644
--- a/lib/msf/core/optional_session.rb
+++ b/lib/msf/core/optional_session.rb
@@ -7,5 +7,9 @@
 module Msf
   module OptionalSession
     include Msf::SessionCompatibility
+
+    def session_enabled?(session_feature_name)
+      framework.features.enabled?(session_feature_name)
+    end
   end
 end
diff --git a/lib/msf/core/optional_session/smb.rb b/lib/msf/core/optional_session/smb.rb
index 9a1c7cc0fa97e..0b73e1f55d6cf 100644
--- a/lib/msf/core/optional_session/smb.rb
+++ b/lib/msf/core/optional_session/smb.rb
@@ -5,6 +5,9 @@ module OptionalSession
     module SMB
       include Msf::OptionalSession
 
+      FEATURE_NAME = Msf::FeatureManager::SMB_SESSION_TYPE
+      RHOST_GROUP_OPTIONS = %w[RHOSTS RPORT SMBDomain SMBUser SMBPass THREADS]
+
       def initialize(info = {})
         super(
           update_info(
@@ -13,24 +16,36 @@ def initialize(info = {})
           )
         )
 
-
-        if framework.features.enabled?(Msf::FeatureManager::SMB_SESSION_TYPE)
+        if session_enabled?
+          session_group = Msf::OptionGroup.new(name: 'SESSION', description: 'Used when connecting via an existing SESSION')
+          rhost_group = Msf::OptionGroup.new(name: 'RHOST', description: 'Used when making a new connection via RHOSTS')
           register_options(
             [
-              Msf::OptInt.new('SESSION', [ false, 'The session to run this module on' ]),
+              Msf::OptInt.new('SESSION', [ false, 'The session to run this module on' ], group: session_group),
               Msf::Opt::RHOST(nil, false),
-              Msf::Opt::RPORT(443, false)
+              Msf::Opt::RPORT(445, false),
             ]
           )
+
+          RHOST_GROUP_OPTIONS.each do |option_name|
+            if options[option_name]
+              options[option_name].group = rhost_group
+            end
+          end
+
           add_info('New in Metasploit 6.4 - This module can target a %grnSESSION%clr or an %grnRHOST%clr')
         end
       end
 
       def session
-        return nil unless framework.features.enabled?(Msf::FeatureManager::SMB_SESSION_TYPE)
+        return nil unless session_enabled?
 
         super
       end
+
+      def session_enabled?
+        super(FEATURE_NAME)
+      end
     end
   end
 end