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 ed6aa6798..5ed349266 100644
--- a/lib/inspec/rule.rb
+++ b/lib/inspec/rule.rb
@@ -174,8 +174,9 @@ module Inspec
       rule.instance_variable_get(:@__skip_rule)
     end
 
-    def self.set_skip_rule(rule, value)
-      rule.instance_variable_set(:@__skip_rule, { result: 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)
diff --git a/test/unit/profiles/profile_context_test.rb b/test/unit/profiles/profile_context_test.rb
index 0859b0ec2..320e691a5 100644
--- a/test/unit/profiles/profile_context_test.rb
+++ b/test/unit/profiles/profile_context_test.rb
@@ -117,6 +117,7 @@ describe Inspec::ProfileContext do
     describe 'global only_if' do
       let(:if_true) { "only_if { true }\n" }
       let(:if_false) { "only_if { false }\n" }
+      let(:if_false_message) { "only_if('if_false_message skipped') { false }\n" }
       let(:describe) { "describe nil do its(:to_i) { should eq rand } end\n" }
       let(:control) { "control 1 do\n#{describe}\nend\n" }
       let(:control_2) { "control 2 do\n#{describe}\nend\n" }
@@ -180,6 +181,14 @@ 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(if_false_message + 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: if_false_message skipped'
+        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)