diff --git a/.rubocop.yml b/.rubocop.yml
index 947d23cc..9a80d12d 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -59,3 +59,9 @@ Style/NegatedIfElseCondition:
   Exclude:
     - 'lib/ronin/exploits/sqli.rb'
     - 'lib/ronin/exploits/mixins/html.rb'
+
+# we need to define a #=== operator for matching payload class(es)
+Style/CaseEquality:
+  Exclude:
+    - 'lib/ronin/exploits/mixins/has_payload.rb'
+    - 'spec/mixins/has_payload_spec.rb'
diff --git a/lib/ronin/exploits/mixins/has_payload.rb b/lib/ronin/exploits/mixins/has_payload.rb
index 93280661..6318286f 100644
--- a/lib/ronin/exploits/mixins/has_payload.rb
+++ b/lib/ronin/exploits/mixins/has_payload.rb
@@ -58,6 +58,57 @@ def self.included(exploit)
           exploit.extend ClassMethods
         end
 
+        #
+        # Helper class for matching a payload against multiple accepted payload
+        # classes.
+        #
+        # @api private
+        #
+        # @since 1.3.0
+        #
+        class PayloadClasses
+
+          # The payload classes to match against.
+          #
+          # @return [Array<Class<Ronin::Payloads::Payload>>]
+          attr_reader :classes
+
+          #
+          # Initializes the payload classes.
+          #
+          # @param [Array<Class<Ronin::Payloads::Payload>>] classes
+          #   The payload classes.
+          #
+          def initialize(classes)
+            @classes = classes
+          end
+
+          #
+          # Compares the payload object to the payload classes.
+          #
+          # @param [Ronin::Payloads::Payload] payload
+          #   The payload object to match.
+          #
+          # @return [Boolean]
+          #   Indicates whether the payload object inherits from any of the
+          #   payload classes.
+          #
+          def ===(payload)
+            @classes.any? { |payload_class| payload_class === payload }
+          end
+
+          #
+          # Converts the list payload classes to a String.
+          #
+          # @return [String]
+          #   The comma separated list of payload class names.
+          #
+          def to_s
+            @classes.join(', ')
+          end
+
+        end
+
         #
         # Class methods.
         #
@@ -72,9 +123,13 @@ module ClassMethods
           # @return [Class<Ronin::Payloads::Payload>]
           #   The exploit's compatible payload base class.
           #
-          def payload_class(new_payload_class=nil)
-            if new_payload_class
-              @payload_class = new_payload_class
+          def payload_class(*new_payload_classes)
+            unless new_payload_classes.empty?
+              @payload_class = if new_payload_classes.length == 1
+                                 new_payload_classes.first
+                               else
+                                 PayloadClasses.new(new_payload_classes)
+                               end
             else
               @payload_class ||= if superclass.kind_of?(ClassMethods)
                                    superclass.payload_class
@@ -113,7 +168,7 @@ def initialize(payload: nil, **kwargs)
         #
         def payload=(new_payload)
           if new_payload.kind_of?(Payloads::Payload)
-            unless new_payload.kind_of?(self.class.payload_class)
+            unless self.class.payload_class === new_payload
               raise(IncompatiblePayload,"incompatible payload, must be a #{self.class.payload_class} payload: #{new_payload.inspect}")
             end
           end
diff --git a/spec/mixins/has_payload_spec.rb b/spec/mixins/has_payload_spec.rb
index cb052160..bdb1e507 100644
--- a/spec/mixins/has_payload_spec.rb
+++ b/spec/mixins/has_payload_spec.rb
@@ -8,6 +8,9 @@ module TestHasPayload
     class TestPayload < Ronin::Payloads::Payload
     end
 
+    class TestPayload2 < Ronin::Payloads::Payload
+    end
+
     class InheritedPayload < TestPayload
     end
 
@@ -24,6 +27,12 @@ class WithPayloadClass < Ronin::Exploits::Exploit
       payload_class TestPayload
     end
 
+    class WithPayloadClasses < Ronin::Exploits::Exploit
+      include Ronin::Exploits::Mixins::HasPayload
+
+      payload_class TestPayload, TestPayload2
+    end
+
     class InheritesPayloadClass < WithPayloadClass
     end
 
@@ -32,6 +41,46 @@ class InheritesAndOverridesPayloadClass < WithPayloadClass
     end
   end
 
+  describe described_class::PayloadClasses do
+    let(:classes) do
+      [TestHasPayload::TestPayload, TestHasPayload::TestPayload2]
+    end
+
+    subject { described_class.new(classes) }
+
+    describe "#initialize" do
+      it "must set #classes" do
+        expect(subject.classes).to eq(classes)
+      end
+    end
+
+    describe "#===" do
+      context "when the given payload object is kind of one of the payload classes" do
+        let(:payload) { TestHasPayload::TestPayload2.new }
+
+        it "must return true" do
+          expect(subject === payload).to be(true)
+        end
+      end
+
+      context "when the given payload object is not kind of any of the payload classes" do
+        let(:payload) { TestHasPayload::TestOtherPayload.new }
+
+        it "must return false" do
+          expect(subject === payload).to be(false)
+        end
+      end
+    end
+
+    describe "#to_s" do
+      it "must return a comma-separated String of the class names" do
+        expect(subject.to_s).to eq(
+          "#{TestHasPayload::TestPayload}, #{TestHasPayload::TestPayload2}"
+        )
+      end
+    end
+  end
+
   describe ".payload_class" do
     subject { test_class }
 
@@ -44,10 +93,23 @@ class InheritesAndOverridesPayloadClass < WithPayloadClass
     end
 
     context "when the payload_class has been set in the Exploit class" do
-      let(:test_class) { TestHasPayload::WithPayloadClass }
+      context "with a single payload class" do
+        let(:test_class) { TestHasPayload::WithPayloadClass }
 
-      it "must set the payload_class to the given payload class" do
-        expect(subject.payload_class).to be(TestHasPayload::TestPayload)
+        it "must set the payload_class to the given payload class" do
+          expect(subject.payload_class).to be(TestHasPayload::TestPayload)
+        end
+      end
+
+      context "with multiple payload classes" do
+        let(:test_class) { TestHasPayload::WithPayloadClasses }
+
+        it "must set payload_class to a #{described_class}::PayloadClasses objects with the given payload classes" do
+          expect(subject.payload_class).to be_kind_of(described_class::PayloadClasses)
+          expect(subject.payload_class.classes).to eq(
+            [TestHasPayload::TestPayload, TestHasPayload::TestPayload2]
+          )
+        end
       end
     end
 
@@ -156,35 +218,71 @@ class InheritesAndOverridesPayloadClass < WithPayloadClass
       end
 
       context "but the Exploit has defined a payload_class" do
-        let(:test_class) { TestHasPayload::WithPayloadClass }
+        context "with a single payload class" do
+          let(:test_class) { TestHasPayload::WithPayloadClass }
 
-        context "and the given payload object is a kind of payload_class" do
-          let(:payload) { test_class.payload_class.new }
+          context "and the given payload object is a kind of payload_class" do
+            let(:payload) { test_class.payload_class.new }
 
-          before { subject.payload = payload }
+            before { subject.payload = payload }
 
-          it "must set #payload" do
-            expect(subject.payload).to be(payload)
+            it "must set #payload" do
+              expect(subject.payload).to be(payload)
+            end
           end
-        end
 
-        context "and the given payload object inherits from payload_class" do
-          let(:payload) { TestHasPayload::InheritedPayload.new }
+          context "and the given payload object inherits from payload_class" do
+            let(:payload) { TestHasPayload::InheritedPayload.new }
 
-          before { subject.payload = payload }
+            before { subject.payload = payload }
 
-          it "must set #payload" do
-            expect(subject.payload).to be(payload)
+            it "must set #payload" do
+              expect(subject.payload).to be(payload)
+            end
+          end
+
+          context "but the given payload is not a kind of payload_class" do
+            let(:payload) { TestHasPayload::TestOtherPayload.new }
+
+            it do
+              expect {
+                subject.payload = payload
+              }.to raise_error(Ronin::Exploits::IncompatiblePayload,"incompatible payload, must be a #{test_class.payload_class} payload: #{payload.inspect}")
+            end
           end
         end
 
-        context "but the given payload is not a kind of payload_class" do
-          let(:payload) { TestHasPayload::TestOtherPayload.new }
+        context "with multiple payload classes" do
+          let(:test_class) { TestHasPayload::WithPayloadClasses }
+
+          context "and the given payload object is a kind of payload_class" do
+            let(:payload) { test_class.payload_class.classes.last.new }
+
+            before { subject.payload = payload }
+
+            it "must set #payload" do
+              expect(subject.payload).to be(payload)
+            end
+          end
+
+          context "and the given payload object inherits from payload_class" do
+            let(:payload) { TestHasPayload::InheritedPayload.new }
+
+            before { subject.payload = payload }
+
+            it "must set #payload" do
+              expect(subject.payload).to be(payload)
+            end
+          end
+
+          context "but the given payload is not a kind of payload_class" do
+            let(:payload) { TestHasPayload::TestOtherPayload.new }
 
-          it do
-            expect {
-              subject.payload = payload
-            }.to raise_error(Ronin::Exploits::IncompatiblePayload,"incompatible payload, must be a #{test_class.payload_class} payload: #{payload.inspect}")
+            it do
+              expect {
+                subject.payload = payload
+              }.to raise_error(Ronin::Exploits::IncompatiblePayload,"incompatible payload, must be a #{test_class.payload_class} payload: #{payload.inspect}")
+            end
           end
         end
       end