diff --git a/NEWS.md b/NEWS.md
index ebc6c220..85de8010 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -1,3 +1,15 @@
+# HEAD
+
+### Features
+
+* Update `dependent` qualifier on association matchers to support `:destroy`,
+  `:delete`, `:nullify`, `:restrict`, `:restrict_with_exception`, and
+  `:restrict_with_error`. You can also pass `true` or `false` to assert that
+  the association has (or has not) been declared with *any* dependent option.
+  ([#631])
+
+[#631]: https://github.com/thoughtbot/shoulda-matchers/pull/631
+
 # 2.8.0.rc1
 
 ### Deprecations
diff --git a/lib/shoulda/matchers/active_record/association_matcher.rb b/lib/shoulda/matchers/active_record/association_matcher.rb
index a336661b..cf596e07 100644
--- a/lib/shoulda/matchers/active_record/association_matcher.rb
+++ b/lib/shoulda/matchers/active_record/association_matcher.rb
@@ -162,6 +162,24 @@ module Shoulda
       #       should belong_to(:world).dependent(:destroy)
       #     end
       #
+      # To assert that *any* `:dependent` option was specified, use `true`:
+      #
+      #     # RSpec
+      #     describe Person do
+      #       it { should belong_to(:world).dependent(true) }
+      #     end
+      #
+      # To assert that *no* `:dependent` option was specified, use `false`:
+      #
+      #     class Person < ActiveRecord::Base
+      #       belongs_to :company
+      #     end
+      #
+      #     # RSpec
+      #     describe Person do
+      #       it { should belong_to(:company).dependent(false) }
+      #     end
+      #
       # ##### counter_cache
       #
       # Use `counter_cache` to assert that the `:counter_cache` option was
@@ -993,7 +1011,7 @@ module Shoulda
         end
 
         def macro_supports_primary_key?
-          macro == :belongs_to || 
+          macro == :belongs_to ||
             ([:has_many, :has_one].include?(macro) && !through?)
         end
 
diff --git a/lib/shoulda/matchers/active_record/association_matchers/dependent_matcher.rb b/lib/shoulda/matchers/active_record/association_matchers/dependent_matcher.rb
index 4c68364c..973433a0 100644
--- a/lib/shoulda/matchers/active_record/association_matchers/dependent_matcher.rb
+++ b/lib/shoulda/matchers/active_record/association_matchers/dependent_matcher.rb
@@ -19,10 +19,10 @@ module Shoulda
           def matches?(subject)
             self.subject = ModelReflector.new(subject, name)
 
-            if option_verifier.correct_for_string?(:dependent, dependent)
+            if option_matches?
               true
             else
-              self.missing_option = "#{name} should have #{dependent} dependency"
+              self.missing_option = generate_missing_option
               false
             end
           end
@@ -31,9 +31,30 @@ module Shoulda
 
           attr_accessor :subject, :dependent, :name
 
+          private
+
           def option_verifier
             @option_verifier ||= OptionVerifier.new(subject)
           end
+
+          def option_matches?
+            option_verifier.correct_for?(option_type, :dependent, dependent)
+          end
+
+          def option_type
+            case dependent
+              when true, false then :boolean
+              else :string
+            end
+          end
+
+          def generate_missing_option
+            [
+              "#{name} should have",
+              (dependent == true ? 'a' : dependent),
+              'dependency'
+            ].join(' ')
+          end
         end
       end
     end
diff --git a/lib/shoulda/matchers/active_record/association_matchers/option_verifier.rb b/lib/shoulda/matchers/active_record/association_matchers/option_verifier.rb
index 84debf62..999feb7a 100644
--- a/lib/shoulda/matchers/active_record/association_matchers/option_verifier.rb
+++ b/lib/shoulda/matchers/active_record/association_matchers/option_verifier.rb
@@ -32,6 +32,20 @@ module Shoulda
             correct_for?(:relation_clause, name, expected_value)
           end
 
+          def correct_for?(*args)
+            expected_value, name, type = args.reverse
+            if expected_value.nil?
+              true
+            else
+              expected_value = type_cast(
+                type,
+                expected_value_for(type, name, expected_value)
+              )
+              actual_value = type_cast(type, actual_value_for(name))
+              expected_value == actual_value
+            end
+          end
+
           def actual_value_for(name)
             if RELATION_OPTIONS.include?(name)
               actual_value_for_relation_clause(name)
@@ -49,17 +63,6 @@ module Shoulda
 
           attr_reader :reflector
 
-          def correct_for?(*args)
-            expected_value, name, type = args.reverse
-            if expected_value.nil?
-              true
-            else
-              expected_value = type_cast(type, expected_value_for(type, name, expected_value))
-              actual_value = type_cast(type, actual_value_for(name))
-              expected_value == actual_value
-            end
-          end
-
           def type_cast(type, value)
             case type
               when :string, :relation_clause then value.to_s
diff --git a/spec/unit/shoulda/matchers/active_record/association_matcher_spec.rb b/spec/unit/shoulda/matchers/active_record/association_matcher_spec.rb
index b0ab0307..da8f20ba 100644
--- a/spec/unit/shoulda/matchers/active_record/association_matcher_spec.rb
+++ b/spec/unit/shoulda/matchers/active_record/association_matcher_spec.rb
@@ -646,8 +646,28 @@ describe Shoulda::Matchers::ActiveRecord::AssociationMatcher, type: :model do
     end
 
     it 'accepts an association with a valid :dependent option' do
-      expect(having_one_detail(dependent: :destroy)).
-        to have_one(:detail).dependent(:destroy)
+      dependent_options.each do |option|
+        expect(having_one_detail(dependent: option)).
+          to have_one(:detail).dependent(option)
+      end
+    end
+
+    it 'accepts any dependent option if true' do
+      dependent_options.each do |option|
+        expect(having_one_detail(dependent: option)).
+          to have_one(:detail).dependent(true)
+      end
+    end
+
+    it 'rejects any dependent options if false' do
+      dependent_options.each do |option|
+        expect(having_one_detail(dependent: option)).
+          to_not have_one(:detail).dependent(false)
+      end
+    end
+
+    it 'accepts a nil dependent option if false' do
+      expect(having_one_detail).to have_one(:detail).dependent(false)
     end
 
     it 'rejects an association with a bad :dependent option' do
@@ -1117,4 +1137,13 @@ describe Shoulda::Matchers::ActiveRecord::AssociationMatcher, type: :model do
     args << options
     model.__send__(macro, name, *args)
   end
+
+  def dependent_options
+    case Rails.version
+    when /\A3/
+      [:destroy, :delete, :nullify, :restrict]
+    when /\A4/
+      [:destroy, :delete, :nullify, :restrict_with_exception, :restrict_with_error]
+    end
+  end
 end