diff --git a/lib/inspec/control_eval_context.rb b/lib/inspec/control_eval_context.rb
index 0b87bcccc..df8ec4f73 100644
--- a/lib/inspec/control_eval_context.rb
+++ b/lib/inspec/control_eval_context.rb
@@ -52,6 +52,7 @@ module Inspec
           @conf = conf
           @dependencies = dependencies
           @require_loader = require_loader
+          @skip_file_message = nil
           @skip_file = false
           @skip_only_if_eval = skip_only_if_eval
         end
@@ -118,18 +119,18 @@ module Inspec
 
         define_method :register_control do |control, &block|
           if @skip_file
-            ::Inspec::Rule.set_skip_rule(control, true)
+            ::Inspec::Rule.set_skip_rule(control, true, @skip_file_message)
           end
 
           unless profile_context_owner.profile_supports_platform?
             platform = inspec.platform
             msg = "Profile #{profile_context_owner.profile_id} is not supported on platform #{platform.name}/#{platform.release}."
-            ::Inspec::Rule.set_skip_rule(control, msg)
+            ::Inspec::Rule.set_skip_rule(control, true, msg)
           end
 
           unless profile_context_owner.profile_supports_inspec_version?
             msg = "Profile #{profile_context_owner.profile_id} is not supported on InSpec version (#{Inspec::VERSION})."
-            ::Inspec::Rule.set_skip_rule(control, msg)
+            ::Inspec::Rule.set_skip_rule(control, true, msg)
           end
 
           profile_context_owner.register_rule(control, &block) unless control.nil?
@@ -144,19 +145,19 @@ module Inspec
           profile_context_owner.unregister_rule(id)
         end
 
-        define_method :only_if do |&block|
+        define_method :only_if do |message = nil, &block|
           return unless block
           return if @skip_file == true
           return if @skip_only_if_eval == true
 
           return if block.yield == true
-
           # Apply `set_skip_rule` for other rules in the same file
           profile_context_owner.rules.values.each do |r|
             sources_match = r.source_file == block.source_location[0]
-            Inspec::Rule.set_skip_rule(r, true) if sources_match
+            Inspec::Rule.set_skip_rule(r, true, message) if sources_match
           end
 
+          @skip_file_message = message
           @skip_file = true
         end
 
diff --git a/lib/inspec/rule.rb b/lib/inspec/rule.rb
index 18da0d162..d3f45a75b 100644
--- a/lib/inspec/rule.rb
+++ b/lib/inspec/rule.rb
@@ -42,7 +42,7 @@ module Inspec
       @__rule_id = id
       @__profile_id = profile_id
       @__checks = []
-      @__skip_rule = nil
+      @__skip_rule = {}
       @__merge_count = 0
       @__merge_changes = []
       @__skip_only_if_eval = opts[:skip_only_if_eval]
@@ -118,11 +118,12 @@ module Inspec
     #
     # @param [Type] &block returns true if tests are added, false otherwise
     # @return [nil]
-    def only_if
+    def only_if(message = nil)
       return unless block_given?
       return if @__skip_only_if_eval == true
 
-      @__skip_rule ||= !yield
+      @__skip_rule[:result] ||= !yield
+      @__skip_rule[:message] = message
     end
 
     # Describe will add one or more tests to this control. There is 2 ways
@@ -174,8 +175,9 @@ module Inspec
       rule.instance_variable_get(:@__skip_rule)
     end
 
-    def self.set_skip_rule(rule, value)
-      rule.instance_variable_set(:@__skip_rule, value)
+    def self.set_skip_rule(rule, value, message = nil)
+      rule.instance_variable_set(:@__skip_rule,
+                                 { result: value, message: message })
     end
 
     def self.merge_count(rule)
@@ -187,9 +189,13 @@ module Inspec
     end
 
     def self.prepare_checks(rule)
-      msg = skip_status(rule)
-      return checks(rule) unless msg
-      msg = 'Skipped control due to only_if condition.' if msg == true
+      skip_check = skip_status(rule)
+      return checks(rule) unless skip_check[:result].eql?(true)
+      if skip_check[:message]
+        msg = "Skipped control due to only_if condition: #{skip_check[:message]}"
+      else
+        msg = 'Skipped control due to only_if condition.'
+      end
 
       # TODO: we use os as the carrier here, but should consider
       # a separate resource to do skipping
diff --git a/test/unit/profiles/profile_context_test.rb b/test/unit/profiles/profile_context_test.rb
index 0859b0ec2..458fea22a 100644
--- a/test/unit/profiles/profile_context_test.rb
+++ b/test/unit/profiles/profile_context_test.rb
@@ -180,6 +180,15 @@ describe Inspec::ProfileContext do
         get_checks[0][1][0].resource_failed?.must_equal false
       end
 
+      it 'allows specifying a message with true only_if' do
+        profile.load("only_if('this is a only_if skipped message') { false }\n" + control)
+        get_checks.length.must_equal 1
+        get_checks[0][1][0].resource_skipped?.must_equal true
+        get_checks[0][1][0].resource_exception_message.must_equal 'Skipped' \
+         ' control due to only_if condition: this is a only_if skipped message'
+        get_checks[0][1][0].resource_failed?.must_equal false
+      end
+
       it 'doesnt extend into other control files' do
         fake_control_file = if_false + control
         profile.load_control_file(fake_control_file, '(eval)', nil)