diff --git a/CHANGELOG.md b/CHANGELOG.md
index ddcdc86..72d1db9 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,7 +6,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 ### Added
-- Added ability to cast types using the return value from expect statements with a type matcher.
+- Added ability to cast types using the return value from expect/should statements with a type matcher.
 
 ### Fixed
 - Fix invalid syntax (unterminated call) when recording calls to stubs with an un-named splat.
diff --git a/spec/features/expect_type_spec.cr b/spec/features/expect_type_spec.cr
index 6991a8a..6ed9949 100644
--- a/spec/features/expect_type_spec.cr
+++ b/spec/features/expect_type_spec.cr
@@ -1,36 +1,70 @@
 require "../spec_helper"
 
-Spectator.describe "Expect Type" do
-  it "ensures a type is cast" do
-    value = 42.as(String | Int32)
-    expect(value).to be_a(String | Int32)
-    expect(value).to compile_as(String | Int32)
-    value = expect(value).to be_a(Int32)
-    expect(value).to eq(42)
-    expect(value).to be_a(Int32)
-    expect(value).to compile_as(Int32)
-    expect(value).to_not respond_to(:downcase)
+Spectator.describe "Expect Type", :smoke do
+  context "with expect syntax" do
+    it "ensures a type is cast" do
+      value = 42.as(String | Int32)
+      expect(value).to be_a(String | Int32)
+      expect(value).to compile_as(String | Int32)
+      value = expect(value).to be_a(Int32)
+      expect(value).to eq(42)
+      expect(value).to be_a(Int32)
+      expect(value).to compile_as(Int32)
+      expect(value).to_not respond_to(:downcase)
+    end
+
+    it "ensures a type is not nil" do
+      value = 42.as(Int32?)
+      expect(value).to be_a(Int32?)
+      expect(value).to compile_as(Int32?)
+      value = expect(value).to_not be_nil
+      expect(value).to eq(42)
+      expect(value).to be_a(Int32)
+      expect(value).to compile_as(Int32)
+      expect { value.not_nil! }.to_not raise_error(NilAssertionError)
+    end
+
+    it "removes types from a union" do
+      value = 42.as(String | Int32)
+      expect(value).to be_a(String | Int32)
+      expect(value).to compile_as(String | Int32)
+      value = expect(value).to_not be_a(String)
+      expect(value).to eq(42)
+      expect(value).to be_a(Int32)
+      expect(value).to compile_as(Int32)
+      expect(value).to_not respond_to(:downcase)
+    end
   end
 
-  it "ensures a type is not nil" do
-    value = 42.as(Int32?)
-    expect(value).to be_a(Int32?)
-    expect(value).to compile_as(Int32?)
-    value = expect(value).to_not be_nil
-    expect(value).to eq(42)
-    expect(value).to be_a(Int32)
-    expect(value).to compile_as(Int32)
-    expect { value.not_nil! }.to_not raise_error(NilAssertionError)
-  end
+  context "with should syntax" do
+    it "ensures a type is cast" do
+      value = 42.as(String | Int32)
+      value.should be_a(String | Int32)
+      value = value.should be_a(Int32)
+      value.should eq(42)
+      value.should be_a(Int32)
+      value.should compile_as(Int32)
+      value.should_not respond_to(:downcase)
+    end
 
-  it "removes types from a union" do
-    value = 42.as(String | Int32)
-    expect(value).to be_a(String | Int32)
-    expect(value).to compile_as(String | Int32)
-    value = expect(value).to_not be_a(String)
-    expect(value).to eq(42)
-    expect(value).to be_a(Int32)
-    expect(value).to compile_as(Int32)
-    expect(value).to_not respond_to(:downcase)
+    it "ensures a type is not nil" do
+      value = 42.as(Int32?)
+      value.should be_a(Int32?)
+      value = value.should_not be_nil
+      value.should eq(42)
+      value.should be_a(Int32)
+      value.should compile_as(Int32)
+      expect { value.not_nil! }.to_not raise_error(NilAssertionError)
+    end
+
+    it "removes types from a union" do
+      value = 42.as(String | Int32)
+      value.should be_a(String | Int32)
+      value = value.should_not be_a(String)
+      value.should eq(42)
+      value.should be_a(Int32)
+      value.should compile_as(Int32)
+      value.should_not respond_to(:downcase)
+    end
   end
 end
diff --git a/src/spectator/should.cr b/src/spectator/should.cr
index d444c00..f0fe075 100644
--- a/src/spectator/should.cr
+++ b/src/spectator/should.cr
@@ -30,6 +30,23 @@ class Object
     ::Spectator::Harness.current.report(expectation)
   end
 
+  # Asserts that some criteria defined by the matcher is satisfied.
+  # Allows a custom message to be used.
+  # Returns the expected value cast as the expected type, if the matcher is satisfied.
+  def should(matcher : ::Spectator::Matchers::TypeMatcher(U), message = nil, *, _file = __FILE__, _line = __LINE__) forall U
+    actual = ::Spectator::Value.new(self)
+    location = ::Spectator::Location.new(_file, _line)
+    match_data = matcher.match(actual)
+    expectation = ::Spectator::Expectation.new(match_data, location, message)
+    if ::Spectator::Harness.current.report(expectation)
+      return self if self.is_a?(U)
+
+      raise "Spectator bug: expected value should have cast to #{U}"
+    else
+      raise TypeCastError.new("Expected value should be a #{U}, but was actually #{self.class}")
+    end
+  end
+
   # Works the same as `#should` except the condition is inverted.
   # When `#should` succeeds, this method will fail, and vice-versa.
   def should_not(matcher, message = nil, *, _file = __FILE__, _line = __LINE__)
@@ -40,6 +57,40 @@ class Object
     ::Spectator::Harness.current.report(expectation)
   end
 
+  # Asserts that some criteria defined by the matcher is not satisfied.
+  # Allows a custom message to be used.
+  # Returns the expected value cast without the unexpected type, if the matcher is satisfied.
+  def should_not(matcher : ::Spectator::Matchers::TypeMatcher(U), message = nil, *, _file = __FILE__, _line = __LINE__) forall U
+    actual = ::Spectator::Value.new(self)
+    location = ::Spectator::Location.new(_file, _line)
+    match_data = matcher.negated_match(actual)
+    expectation = ::Spectator::Expectation.new(match_data, location, message)
+    if ::Spectator::Harness.current.report(expectation)
+      return self unless self.is_a?(U)
+
+      raise "Spectator bug: expected value should not be #{U}"
+    else
+      raise TypeCastError.new("Expected value is not expected to be a #{U}, but was actually #{self.class}")
+    end
+  end
+
+  # Asserts that some criteria defined by the matcher is not satisfied.
+  # Allows a custom message to be used.
+  # Returns the expected value cast as a non-nillable type, if the matcher is satisfied.
+  def should_not(matcher : ::Spectator::Matchers::NilMatcher, message = nil, *, _file = __FILE__, _line = __LINE__)
+    actual = ::Spectator::Value.new(self)
+    location = ::Spectator::Location.new(_file, _line)
+    match_data = matcher.negated_match(actual)
+    expectation = ::Spectator::Expectation.new(match_data, location, message)
+    if ::Spectator::Harness.current.report(expectation)
+      return self unless self.nil?
+
+      raise "Spectator bug: expected value should not be nil"
+    else
+      raise NilAssertionError.new("Expected value should not be nil.")
+    end
+  end
+
   # Works the same as `#should` except that the condition check is postponed.
   # The expectation is checked after the example finishes and all hooks have run.
   def should_eventually(matcher, message = nil, *, _file = __FILE__, _line = __LINE__)