diff --git a/Gemfile b/Gemfile
index a1b8a69..5c91572 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,4 +1,5 @@
 source "https://rubygems.org"
 
-gem "rspec", "~> 3.4.0"
-gem "whenever", "~> 0.9.4"
+gem "rspec", "~> 3.7"
+gem "whenever", "~> 0.10"
+gem "activesupport", "~> 5.2"
diff --git a/Gemfile.lock b/Gemfile.lock
index d03e4fd..e8cf640 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1,30 +1,43 @@
 GEM
   remote: https://rubygems.org/
   specs:
+    activesupport (5.2.3)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 0.7, < 2)
+      minitest (~> 5.1)
+      tzinfo (~> 1.1)
     chronic (0.10.2)
-    diff-lcs (1.2.5)
-    rspec (3.4.0)
-      rspec-core (~> 3.4.0)
-      rspec-expectations (~> 3.4.0)
-      rspec-mocks (~> 3.4.0)
-    rspec-core (3.4.4)
-      rspec-support (~> 3.4.0)
-    rspec-expectations (3.4.0)
+    concurrent-ruby (1.1.5)
+    diff-lcs (1.3)
+    i18n (1.6.0)
+      concurrent-ruby (~> 1.0)
+    minitest (5.11.3)
+    rspec (3.7.0)
+      rspec-core (~> 3.7.0)
+      rspec-expectations (~> 3.7.0)
+      rspec-mocks (~> 3.7.0)
+    rspec-core (3.7.1)
+      rspec-support (~> 3.7.0)
+    rspec-expectations (3.7.0)
       diff-lcs (>= 1.2.0, < 2.0)
-      rspec-support (~> 3.4.0)
-    rspec-mocks (3.4.1)
+      rspec-support (~> 3.7.0)
+    rspec-mocks (3.7.0)
       diff-lcs (>= 1.2.0, < 2.0)
-      rspec-support (~> 3.4.0)
-    rspec-support (3.4.1)
-    whenever (0.9.4)
+      rspec-support (~> 3.7.0)
+    rspec-support (3.7.1)
+    thread_safe (0.3.6)
+    tzinfo (1.2.5)
+      thread_safe (~> 0.1)
+    whenever (0.10.0)
       chronic (>= 0.6.3)
 
 PLATFORMS
   ruby
 
 DEPENDENCIES
-  rspec (~> 3.4.0)
-  whenever (~> 0.9.4)
+  activesupport (~> 5.2)
+  rspec (~> 3.7)
+  whenever (~> 0.10)
 
 BUNDLED WITH
-   1.11.2
+   1.17.3
diff --git a/README.md b/README.md
index e1478b2..8774097 100644
--- a/README.md
+++ b/README.md
@@ -7,7 +7,7 @@ This gem was born out of a desire to test the schedule for tasks being scheduled
 Add this to you gemfile:
 
 ```ruby
-gem "shoulda-whenever", "~> 0.0.2"
+gem "shoulda-whenever"
 ```
 
 Create a new schedule to be tested at `config/schedule.rb` (or anywhere really, but for the sake of the README, that's where it is):
@@ -31,3 +31,37 @@ describe "Schedule" do
   end
 end
 ```
+
+## Additional Filters
+
+### Mail To
+
+If you need to check the task output is sent to a specific email address.
+
+```ruby
+every :monday, at: "07:00 AM", mailto: "info@test.com" do
+  runner "Notifier.send_good_morning_email"
+end
+```
+
+```ruby
+it "sends out good morning emails every monday at 7:00" do
+  expect(whenever).to schedule("Notifier.send_good_morning_email").every(:monday).at("07:00 AM").with_mailto("info@test.com")
+end
+```
+
+### Roles
+
+If you need to check the task is set for specific roles.
+
+```ruby
+every :monday, at: "07:00 AM", roles: [:web] do
+  runner "Notifier.send_good_morning_email"
+end
+```
+
+```ruby
+it "sends out good morning emails every monday at 7:00 on web servers" do
+  expect(whenever).to schedule("Notifier.send_good_morning_email").every(:monday).at("07:00 AM").with_roles([:web])
+end
+```
diff --git a/lib/shoulda/whenever/schedule_matcher.rb b/lib/shoulda/whenever/schedule_matcher.rb
index da44b08..40fcf37 100644
--- a/lib/shoulda/whenever/schedule_matcher.rb
+++ b/lib/shoulda/whenever/schedule_matcher.rb
@@ -9,17 +9,18 @@ def schedule(task)
     alias_method :schedule_command, :schedule
 
     class ScheduleMatcher
-      attr_reader :duration, :time, :task, :roles
+      attr_reader :duration, :time, :task, :roles, :mailto
 
       def initialize(task)
         @task     = task
         @duration = nil
         @time     = nil
         @roles    = nil
+        @mailto   = :default_mailto
       end
 
       def matches?(subject)
-        jobs = subject.instance_variable_get("@jobs")
+        jobs = get_jobs_by_mailto(subject)
 
         jobs = filter_jobs_by_duration(jobs)
         jobs = filter_jobs_by_time(jobs)
@@ -29,11 +30,17 @@ def matches?(subject)
         jobs.any?
       end
 
+      def get_jobs_by_mailto(subject)
+        subject.instance_variable_get("@jobs")[@mailto] || {}
+      end
+
       def filter_jobs_by_duration(jobs)
         if duration.nil?
           jobs.values.flatten
         else
-          duration_to_fetch = if duration.is_a?(String) || duration.is_a?(Symbol)
+          duration_to_fetch = if duration.is_a?(String) ||
+                                 duration.is_a?(Symbol) ||
+                                 duration.is_a?(ActiveSupport::Duration)
                                 duration
                               else
                                 duration.to_i
@@ -61,6 +68,12 @@ def filter_jobs_by_task(jobs)
         end
       end
 
+      def with_mailto(mailto)
+        @mailto = mailto
+
+        self
+      end
+
       def every(duration)
         @duration = duration
 
@@ -83,6 +96,7 @@ def with_roles(roles)
       def description
         [
           base_description,
+          mailto_description,
           duration_description,
           time_description,
           roles_description
@@ -92,6 +106,7 @@ def description
       def failure_message
         [
           base_failure_message,
+          mailto_description,
           duration_description,
           time_description,
           roles_description
@@ -101,6 +116,7 @@ def failure_message
       def failure_message_when_negated
         [
           base_failure_message_when_negated,
+          mailto_description,
           duration_description,
           time_description,
           roles_description
@@ -113,6 +129,12 @@ def base_description
         "schedule \"#{ task }\""
       end
 
+      def mailto_description
+        unless mailto == :default_mailto
+          "with_mailto \"#{ mailto }\""
+        end
+      end
+
       def duration_description
         unless duration.nil?
           if duration.is_a?(String) || duration.is_a?(Symbol)
diff --git a/lib/shoulda/whenever/version.rb b/lib/shoulda/whenever/version.rb
index e11b6ad..4c69b73 100644
--- a/lib/shoulda/whenever/version.rb
+++ b/lib/shoulda/whenever/version.rb
@@ -1,5 +1,5 @@
 module Shoulda
   module Whenever
-    VERSION = "0.0.2".freeze
+    VERSION = "0.0.3".freeze
   end
 end
diff --git a/shoulda-whenever.gemspec b/shoulda-whenever.gemspec
index cc47705..07eba25 100644
--- a/shoulda-whenever.gemspec
+++ b/shoulda-whenever.gemspec
@@ -16,8 +16,9 @@ Gem::Specification.new do |s|
   s.test_files    = `git ls-files -- {test,spec,features}/*`.split("\n")
   s.require_paths = ["lib"]
 
-  s.required_ruby_version = '>= 1.9.3'
+  s.required_ruby_version = '>= 2.3.8'
 
-  s.add_development_dependency "rspec", "~> 3.4", ">= 3.4.0"
-  s.add_development_dependency "whenever", "~> 0.9.4"
+  s.add_development_dependency "rspec", "~> 3.7"
+  s.add_development_dependency "whenever", "~> 0.10"
+  s.add_development_dependency "activesupport", "~> 5.2"
 end
diff --git a/spec/shoulda/whenever/schedule_matcher_spec.rb b/spec/shoulda/whenever/schedule_matcher_spec.rb
index 87698c5..a1c19cc 100644
--- a/spec/shoulda/whenever/schedule_matcher_spec.rb
+++ b/spec/shoulda/whenever/schedule_matcher_spec.rb
@@ -2,6 +2,7 @@
 require "whenever"
 require "shoulda/whenever/schedule_matcher"
 require "rspec/matchers/fail_matchers"
+require "active_support/duration"
 
 describe Shoulda::Whenever::ScheduleMatcher do
   include Shoulda::Whenever
@@ -16,6 +17,17 @@
       end
     end
 
+    context "with a mailto" do
+      it "includes the mailto under which the task is being scheduled" do
+        expect(
+          described_class.new("rake:every:10:minutes")
+            .every(Whenever::NumericSeconds.seconds(10, "minutes"))
+            .with_mailto('test@info.com')
+            .description
+        ).to eq("schedule \"rake:every:10:minutes\" with_mailto \"test@info.com\" every 600 seconds")
+      end
+    end
+
     context "with a duration" do
       it "includes the duration at which the task is being scheduled" do
         expect(
@@ -107,6 +119,25 @@
     end
   end
 
+  context "a task that is scheduled with a certain mailto" do
+    let(:schedule_string) do
+      <<-SCHEDULE
+        every 3.hours, mailto: 'test@info.com' do
+          rake "rake:every:3:hours"
+        end
+      SCHEDULE
+    end
+
+    it "passes" do
+      expect(whenever).to schedule("rake:every:3:hours").every(Whenever::NumericSeconds.seconds(3, "hours")).with_mailto('test@info.com')
+    end
+     it "fails" do
+       expect {
+         expect(whenever).not_to schedule("rake:every:3:hours").every(Whenever::NumericSeconds.seconds(3, "hours")).with_mailto('test@info.com')
+       }.to fail_with("expected not to schedule \"rake:every:3:hours\" with_mailto \"test@info.com\" every 10800 seconds")
+     end
+  end
+
   context "a task that is scheduled after a certain duration" do
     let(:schedule_string) do
       <<-SCHEDULE