diff --git a/build_tools/spec/changelog_spec.rb b/build_tools/spec/changelog_spec.rb
index f2c767d1ec8..37dc2b4a6bc 100644
--- a/build_tools/spec/changelog_spec.rb
+++ b/build_tools/spec/changelog_spec.rb
@@ -3,7 +3,7 @@
 require_relative 'spec_helper'
 
 module BuildTools
-  describe Changelog do
+  describe Changelog, :jruby_flaky do
 
     let(:path) { Tempfile.create('file').path }
     let(:expected_changelog) { <<-LOG
diff --git a/gems/aws-sdk-core/spec/aws/plugins/endpoint_discovery_spec.rb b/gems/aws-sdk-core/spec/aws/plugins/endpoint_discovery_spec.rb
index 3f1059da84f..b4480ebb7e8 100644
--- a/gems/aws-sdk-core/spec/aws/plugins/endpoint_discovery_spec.rb
+++ b/gems/aws-sdk-core/spec/aws/plugins/endpoint_discovery_spec.rb
@@ -4,7 +4,7 @@
 
 module Aws
   module Plugins
-    describe EndpointDiscovery do
+    describe EndpointDiscovery, :jruby_flaky do
 
       EndpointDiscoveryClient = ApiHelper.sample_service(
         api: {
diff --git a/gems/aws-sdk-core/spec/retry_errors_helper.rb b/gems/aws-sdk-core/spec/retry_errors_helper.rb
index 342edf48f8f..93497664c05 100644
--- a/gems/aws-sdk-core/spec/retry_errors_helper.rb
+++ b/gems/aws-sdk-core/spec/retry_errors_helper.rb
@@ -91,7 +91,7 @@ def apply_expectations(test_case)
   if expected[:clock_correction]
     endpoint = resp.context.http_request.endpoint
     expect(resp.context.config.clock_skew.clock_correction(endpoint))
-      .to be_within(1).of(expected[:clock_correction])
+      .to be_within(5).of(expected[:clock_correction])
   end
 end
 
diff --git a/gems/aws-sdk-core/spec/shared_spec_helper.rb b/gems/aws-sdk-core/spec/shared_spec_helper.rb
index a8413857bf6..6cee7bb4f9a 100644
--- a/gems/aws-sdk-core/spec/shared_spec_helper.rb
+++ b/gems/aws-sdk-core/spec/shared_spec_helper.rb
@@ -51,4 +51,20 @@
 
     Thread.report_on_exception = current_value if current_value
   end
+
+  if defined?(JRUBY_VERSION)
+    config.around(:each, :jruby_flaky) do |example|
+      attempt = 0
+      retries = 3
+      loop do
+        attempt += 1
+        example.run
+        break if !example.exception || attempt >= retries
+
+        # clear the exception, ensuring it can run from a clean state
+        example.example.instance_variable_set(:@exception, nil)
+        redo
+      end
+    end
+  end
 end
diff --git a/gems/aws-sdk-s3/spec/object/download_file_spec.rb b/gems/aws-sdk-s3/spec/object/download_file_spec.rb
index bd398a35800..6bef89df4c6 100644
--- a/gems/aws-sdk-s3/spec/object/download_file_spec.rb
+++ b/gems/aws-sdk-s3/spec/object/download_file_spec.rb
@@ -9,7 +9,7 @@ module S3
       let(:client) { S3::Client.new(stub_responses: true) }
       let(:tmpdir) { Dir.tmpdir }
 
-      describe '#download_file' do
+      describe '#download_file', :jruby_flaky do
         let(:path) { Tempfile.new('destination').path }
 
         let(:small_obj) do
diff --git a/gems/aws-sdk-s3/spec/object/upload_stream_spec.rb b/gems/aws-sdk-s3/spec/object/upload_stream_spec.rb
index b201f8b93e7..1897f82b70e 100644
--- a/gems/aws-sdk-s3/spec/object/upload_stream_spec.rb
+++ b/gems/aws-sdk-s3/spec/object/upload_stream_spec.rb
@@ -8,7 +8,7 @@ module S3
     describe Object do
       let(:client) { S3::Client.new(stub_responses: true) }
 
-      describe '#upload_stream' do
+      describe '#upload_stream', :jruby_flaky do
         let(:object) do
           S3::Object.new(
             bucket_name: 'bucket',