diff --git a/.github/workflows/ruby.yml b/.github/workflows/ruby.yml
index 8e3274e2..b4ea4536 100644
--- a/.github/workflows/ruby.yml
+++ b/.github/workflows/ruby.yml
@@ -17,14 +17,15 @@ jobs:
   test:
     runs-on: ubuntu-latest
     strategy:
+      fail-fast: false
       matrix:
-        ruby-version: ['2.7']
+        ruby-version: ['3.3', '3.2', '3.1', '3.0', '2.7']
     steps:
-    - uses: actions/checkout@v2
+    - uses: actions/checkout@v4
     - name: Set up Ruby
       uses: ruby/setup-ruby@v1
       with:
         ruby-version: ${{ matrix.ruby-version }}
-        bundler-cache: true # runs 'bundle install' and caches installed gems automatically
+        bundler-cache: true
     - name: Run tests
       run: bundle exec rake
diff --git a/Makefile b/Makefile
new file mode 100644
index 00000000..c75bd8c4
--- /dev/null
+++ b/Makefile
@@ -0,0 +1,21 @@
+RUBY_VERSIONS := 2.7 3.0 3.1 3.2 3.3
+TARGETS := $(addprefix test-ruby-,$(RUBY_VERSIONS))
+
+.PHONY: test test-all $(TARGETS)
+
+test-all: $(TARGETS)
+	@echo "All versions passed."
+
+define ruby_test_rule
+test-ruby-$(1):
+	@echo "=== Ruby $(1) ==="
+	@docker run --rm -v "$$(CURDIR):/app" -w /app ruby:$(1) bash -c "\
+		rm -f Gemfile.lock && \
+		gem install bundler -v 2.4.22 --no-document > /dev/null 2>&1 && \
+		bundle install --quiet 2>/dev/null && \
+		bundle exec rake"
+endef
+
+$(foreach v,$(RUBY_VERSIONS),$(eval $(call ruby_test_rule,$(v))))
+
+test: test-ruby-3.3
diff --git a/bin/codedeploy-agent b/bin/codedeploy-agent
index 6c84218e..f47289ed 100755
--- a/bin/codedeploy-agent
+++ b/bin/codedeploy-agent
@@ -2,7 +2,7 @@
 
 $:.unshift File.join(File.dirname(File.expand_path('..', __FILE__)), 'lib')
 
-ruby_versions = ["3.2", "3.1", "3.0", "2.7", "2.6", "2.5", "2.4", "2.3", "2.2", "2.1", "2.0"]
+ruby_versions = ["3.3", "3.2", "3.1", "3.0", "2.7"]
 actual_ruby_version = RUBY_VERSION.split('.').map{|s|s.to_i}
 left_bound = '2.0.0'.split('.').map{|s|s.to_i}
 ruby_bin = nil
diff --git a/bin/install b/bin/install
index b1461555..ce589b85 100755
--- a/bin/install
+++ b/bin/install
@@ -245,8 +245,8 @@ IMDS v2 call is failed
 To use a HTTP proxy, specify --proxy followed by the proxy server
 defined by http://hostname:port
 
-This install script needs Ruby versions 2.x or 3.x installed as a prerequisite.
-Currently recommended Ruby versions are 2.0.0, 2.1.8, 2.2.4, 2.3, 2.4, 2.5, 2.6, 2.7, 3.0, 3.1, and 3.2
+This install script needs Ruby versions 2.7 or 3.[1-3] installed as a prerequisite.
+Currently recommended Ruby versions are 2.7, 3.0, 3.1, 3.2, and 3.3
 If multiple Ruby versions are installed, the default ruby version will be used.
 If the default ruby version does not satisfy requirement, the newest version will be used.
 If you do not have a supported Ruby version installed, please install one of them first.
@@ -255,7 +255,7 @@ EOF
   end
 
   def supported_ruby_versions
-    ['3.2','3.1','3.0', '2.7', '2.6', '2.5', '2.4', '2.3', '2.2', '2.1', '2.0']
+    ['3.3', '3.2', '3.1', '3.0', '2.7']
   end
 
   # check ruby version, only version 2.x 3.x works
diff --git a/codedeploy_agent.gemspec b/codedeploy_agent.gemspec
index e261ec1c..5df7996a 100644
--- a/codedeploy_agent.gemspec
+++ b/codedeploy_agent.gemspec
@@ -9,19 +9,19 @@ Gem::Specification.new do |spec|
   spec.bindir        = ['bin']
   spec.require_paths = ['lib']
   spec.license        = 'Apache-2.0'
-  spec.required_ruby_version = '>= 2.7.0'
+  spec.required_ruby_version = '>= 2.7.0', '< 3.4'
 
-  spec.add_dependency('gli', '~> 2.21')
-  spec.add_dependency('json_pure', '~> 1.6')
-  spec.add_dependency('minitar', '~> 0.6.1')
-  spec.add_dependency('rubyzip', '~> 1.3.0')
-  spec.add_dependency('logging', '~> 2.2')
-  spec.add_dependency('aws-sdk-core', '~> 3')
-  spec.add_dependency('aws-sdk-s3', '~> 1')
-  spec.add_dependency('docopt', '~> 0.5.0')
-  spec.add_dependency('concurrent-ruby', '~> 1.1.9')
-  spec.add_dependency('rexml', '~> 3.3.9')
+  spec.add_dependency('gli', '2.22.2')
+  spec.add_dependency('json_pure', '2.8.1')
+  spec.add_dependency('minitar', '0.12.1')
+  spec.add_dependency('rubyzip', '2.4.1')
+  spec.add_dependency('logging', '2.4.0')
+  spec.add_dependency('aws-sdk-core', '3.246.0')
+  spec.add_dependency('aws-sdk-s3', '1.220.0')
+  spec.add_dependency('docopt', '0.5.0')
+  spec.add_dependency('concurrent-ruby', '1.1.10')
+  spec.add_dependency('rexml', '3.3.9')
 
-  spec.add_development_dependency('rake', '~> 12.3.3')
-  spec.add_development_dependency('rspec', '~> 3.2.0')
+  spec.add_development_dependency('rake', '13.4.2')
+  spec.add_development_dependency('rspec', '3.13.2')
 end
diff --git a/features/step_definitions/codedeploy_local_steps.rb b/features/step_definitions/codedeploy_local_steps.rb
index 7b93aa1e..48e032f2 100644
--- a/features/step_definitions/codedeploy_local_steps.rb
+++ b/features/step_definitions/codedeploy_local_steps.rb
@@ -1,7 +1,6 @@
-require 'archive/tar/minitar'
+require 'minitar'
 require 'zlib'
 require 'pathname'
-include Archive::Tar
 
 $:.unshift File.join(File.dirname(File.expand_path('../../..', __FILE__)), 'lib')
 $:.unshift File.join(File.dirname(File.expand_path('../../..', __FILE__)), 'features')
diff --git a/lib/instance_agent/platform/windows_util.rb b/lib/instance_agent/platform/windows_util.rb
index 6238b9a4..600af44f 100644
--- a/lib/instance_agent/platform/windows_util.rb
+++ b/lib/instance_agent/platform/windows_util.rb
@@ -1,6 +1,5 @@
-require 'archive/tar/minitar'
+require 'minitar'
 require 'zlib'
-include Archive::Tar
 
 module InstanceAgent
 
diff --git a/lib/instance_agent/plugins/codedeploy/command_executor.rb b/lib/instance_agent/plugins/codedeploy/command_executor.rb
index defc7fb8..6db2ff43 100644
--- a/lib/instance_agent/plugins/codedeploy/command_executor.rb
+++ b/lib/instance_agent/plugins/codedeploy/command_executor.rb
@@ -505,7 +505,12 @@ def unpack_bundle(cmd, bundle_file, deployment_spec)
                 zipfile.each do |f|
                   file_dst = File.join(dst, f.name)
                   FileUtils.mkdir_p(File.dirname(file_dst))
-                  zipfile.extract(f, file_dst) { true }
+                  FileUtils.rm_f(file_dst)
+                  if Gem::Version.new(Gem.loaded_specs['rubyzip'].version) >= Gem::Version.new('3.0')
+                    zipfile.extract(f, destination_directory: dst)
+                  else
+                    zipfile.extract(f, file_dst)
+                  end
                 end
               end
             end
diff --git a/test/instance_agent/plugins/codedeploy/deployment_specification_test.rb b/test/instance_agent/plugins/codedeploy/deployment_specification_test.rb
index 2b0c4af1..b939318b 100644
--- a/test/instance_agent/plugins/codedeploy/deployment_specification_test.rb
+++ b/test/instance_agent/plugins/codedeploy/deployment_specification_test.rb
@@ -480,13 +480,14 @@ def generate_signed_message_for(map)
         should "raise when JSON submitted as PKCS7/JSON" do
           @packed_message.payload = @deployment_spec.to_json
 
-          assert_raised_with_message("Could not parse the PKCS7: nested asn1 error") do
+          error = assert_raise(RuntimeError) do
             begin
               InstanceAgent::Plugins::CodeDeployPlugin::DeploymentSpecification.parse(@packed_message)
             rescue ArgumentError => e
               raise e.message
             end
           end
+          assert_match(/Could not parse the PKCS7: (nested asn1 error|no start line)/, error.message)
         end
       end
 
@@ -591,13 +592,14 @@ def generate_signed_message_for(map)
         should "raise when JSON submitted as PKCS7/JSON" do
           @packed_local_revision_message.payload = @deployment_local_revision_spec.to_json
 
-          assert_raised_with_message("Could not parse the PKCS7: nested asn1 error") do
+          error = assert_raise(RuntimeError) do
             begin
               InstanceAgent::Plugins::CodeDeployPlugin::DeploymentSpecification.parse(@packed_local_revision_message)
             rescue ArgumentError => e
               raise e.message
             end
           end
+          assert_match(/Could not parse the PKCS7: (nested asn1 error|no start line)/, error.message)
         end
       end
 
diff --git a/test/instance_agent/plugins/codedeploy/unpack_bundle_test.rb b/test/instance_agent/plugins/codedeploy/unpack_bundle_test.rb
index ad55f47d..2b61b30f 100644
--- a/test/instance_agent/plugins/codedeploy/unpack_bundle_test.rb
+++ b/test/instance_agent/plugins/codedeploy/unpack_bundle_test.rb
@@ -28,7 +28,7 @@ def setup_local_file_bundle
     end
     # create the bundle as a local zip file
     @local_file_location = File.join(@local_file_directory, "bundle.zip")
-    Zip::File.open(@local_file_location, Zip::File::CREATE) do |zipfile|
+    Zip::File.open(@local_file_location, create: true) do |zipfile|
       input_filenames.each do |filename|
         zipfile.add(filename, File.join(@local_file_directory, filename))
       end