diff --git a/clockwork.gemspec b/clockwork.gemspec
index 954dfe1..20eaea3 100644
--- a/clockwork.gemspec
+++ b/clockwork.gemspec
@@ -26,4 +26,5 @@ Gem::Specification.new do |s|
   s.add_development_dependency "minitest", "~> 5.8"
   s.add_development_dependency "mocha"
   s.add_development_dependency "test-unit"
+  s.add_development_dependency "timecop"
 end
diff --git a/lib/clockwork/event.rb b/lib/clockwork/event.rb
index 0d7f333..848ee5e 100644
--- a/lib/clockwork/event.rb
+++ b/lib/clockwork/event.rb
@@ -1,6 +1,6 @@
 module Clockwork
   class Event
-    attr_accessor :job, :last
+    attr_accessor :job, :last, :skip_first_run
 
     def initialize(manager, period, job, block, options={})
       validate_if_option(options[:if])
@@ -12,8 +12,8 @@ def initialize(manager, period, job, block, options={})
       @if = options[:if]
       @thread = options.fetch(:thread, @manager.config[:thread])
       @timezone = options.fetch(:tz, @manager.config[:tz])
-      @skip_first_run = options[:skip_first_run]
-      @last = @skip_first_run ? convert_timezone(Time.now) : nil
+      @skip_first_run = options.fetch(:skip_first_run, false)
+      @last = nil
     end
 
     def convert_timezone(t)
diff --git a/lib/clockwork/manager.rb b/lib/clockwork/manager.rb
index 55ec497..46467df 100644
--- a/lib/clockwork/manager.rb
+++ b/lib/clockwork/manager.rb
@@ -160,7 +160,8 @@ def log(msg)
 
     private
     def events_to_run(t)
-      @events.select{ |event| event.run_now?(t) }
+      events_to_run = @events.select{ |event| event.run_now?(t) }
+      clear_first_run_skips(events_to_run)
     end
 
     def register(period, job, block, options)
@@ -176,5 +177,23 @@ def every_with_multiple_times(period, job, options={}, &block)
         register(period, job, block, each_options)
       end
     end
+
+    def clear_first_run_skips(events_to_run)
+      skippable_events = events_to_run.select(&:skip_first_run)
+      return events_to_run if skippable_events.empty?
+      events_to_run.reject!(&:skip_first_run)
+      skippable_events.each do |event|
+        clear_skips(event)
+        event.last = Time.now
+      end
+      events_to_run
+    end
+
+    def clear_skips(event)
+      return unless event.skip_first_run
+      @events.select { |e| e.to_s == event.to_s }.each do |selected_event|
+        selected_event.skip_first_run = false
+      end
+    end
   end
 end
diff --git a/test/database_events/test_helpers.rb b/test/database_events/test_helpers.rb
index 7f25da0..f2fddcc 100644
--- a/test/database_events/test_helpers.rb
+++ b/test/database_events/test_helpers.rb
@@ -68,4 +68,4 @@ def name
   def if?(time)
     @if_state
   end
-end
\ No newline at end of file
+end
diff --git a/test/event_test.rb b/test/event_test.rb
index 2ef77b6..566a426 100644
--- a/test/event_test.rb
+++ b/test/event_test.rb
@@ -34,41 +34,4 @@
       end
     end
   end
-
-  describe '#run_now?' do
-    before do
-      @manager = Class.new
-      @manager.stubs(:config).returns({})
-    end
-
-    describe 'event skip_first_run option set to true' do
-      it 'returns false on first attempt' do
-        event = Clockwork::Event.new(@manager, 1, nil, nil, :skip_first_run => true)
-        assert_equal false, event.run_now?(Time.now)
-      end
-
-      it 'returns true on subsequent attempts' do
-        event = Clockwork::Event.new(@manager, 1, nil, nil, :skip_first_run => true)
-        # first run
-        event.run_now?(Time.now)
-
-        # second run
-        assert_equal true, event.run_now?(Time.now + 1)
-      end
-    end
-
-    describe 'event skip_first_run option not set' do
-      it 'returns true on first attempt' do
-        event = Clockwork::Event.new(@manager, 1, nil, nil)
-        assert_equal true, event.run_now?(Time.now + 1)
-      end
-    end
-
-    describe 'event skip_first_run option set to false' do
-      it 'returns true on first attempt' do
-        event = Clockwork::Event.new(@manager, 1, nil, nil, :skip_first_run => false)
-        assert_equal true, event.run_now?(Time.now)
-      end
-    end
-  end
 end
diff --git a/test/manager_test.rb b/test/manager_test.rb
index c102c43..48c3638 100644
--- a/test/manager_test.rb
+++ b/test/manager_test.rb
@@ -2,6 +2,7 @@
 require "minitest/autorun"
 require 'mocha/setup'
 require 'time'
+require 'timecop'
 require 'active_support/time'
 
 describe Clockwork::Manager do
@@ -185,6 +186,36 @@ def assert_wont_run(t)
       assert_will_run 'jan 1 2010 18:10:00'
       assert_wont_run 'jan 1 2010 18:10:01'
     end
+
+    it "once a day with :skip_first_run" do
+      Timecop.travel Time.new(2010, 1, 1, 16, 19, 59) do
+        @manager.every(5.minutes, 'myjob', :at => "16:20", :skip_first_run => true)
+
+        assert_wont_run 'jan 1 2010 16:19:59'
+        assert_wont_run 'jan 1 2010 16:20:00'
+        assert_wont_run 'jan 1 2010 16:20:01'
+        assert_wont_run 'jan 2 2010 16:19:59'
+        assert_will_run 'jan 2 2010 16:20:00'
+        assert_will_run 'jan 3 2010 16:20:00'
+      end
+    end
+
+    it "twice a day with :skip_first_run" do
+      Timecop.travel Time.new(2010, 1, 1, 16, 19, 59) do
+        @manager.every(1.day, 'myjob', :at => ['18:10', '16:20'], :skip_first_run => true)
+
+        assert_wont_run 'jan 1 2010 16:19:59'
+        assert_wont_run 'jan 1 2010 16:20:00'
+        assert_wont_run 'jan 1 2010 16:20:01'
+
+        assert_wont_run 'jan 1 2010 18:09:59'
+        assert_will_run 'jan 1 2010 18:10:00'
+        assert_wont_run 'jan 1 2010 18:10:01'
+
+        assert_will_run 'jan 2 2010 16:20:00'
+        assert_will_run 'jan 2 2010 18:10:00'
+      end
+    end
   end
 
   describe ':tz option' do