diff --git a/lib/pluginmanager/utils/downloader.rb b/lib/pluginmanager/utils/downloader.rb
index 0d520febf..d2092f221 100644
--- a/lib/pluginmanager/utils/downloader.rb
+++ b/lib/pluginmanager/utils/downloader.rb
@@ -68,7 +68,7 @@ module LogStash module PluginManager module Utils
           downloaded_file.path
         end
       rescue => e
-        downloaded_file.close rescue nil
+        downloaded_file.close unless downloaded_file.closed?
         FileUtils.rm_rf(download_to)
         raise e
       end
diff --git a/logstash-core/lib/logstash/config/source/local.rb b/logstash-core/lib/logstash/config/source/local.rb
index 4dc46414e..897738e12 100644
--- a/logstash-core/lib/logstash/config/source/local.rb
+++ b/logstash-core/lib/logstash/config/source/local.rb
@@ -71,7 +71,8 @@ module LogStash module Config module Source
           end
 
           config_string = ::File.read(file)
-
+          config_string.force_encoding("UTF-8")
+          
           if config_string.valid_encoding?
             part = org.logstash.common.SourceWithMetadata.new("file", file, 0, 0, config_string)
             config_parts << part
diff --git a/logstash-core/spec/logstash/agent_spec.rb b/logstash-core/spec/logstash/agent_spec.rb
index 49752a225..77c277e53 100644
--- a/logstash-core/spec/logstash/agent_spec.rb
+++ b/logstash-core/spec/logstash/agent_spec.rb
@@ -35,7 +35,7 @@ describe LogStash::Agent do
     # This MUST run first, before `subject` is invoked to ensure clean state
     clear_data_dir
 
-    File.open(config_file, "w") { |f| f.puts config_file_txt }
+    File.open(config_file, "w") { |f| f.puts(config_file_txt) }
 
     agent_args.each do |key, value|
       agent_settings.set(key, value)
@@ -52,8 +52,9 @@ describe LogStash::Agent do
   after :each do
     subject.shutdown
     LogStash::SETTINGS.reset
-    File.unlink(config_file)
-    File.unlink(subject.id_path)
+
+    FileUtils.rm(config_file)
+    FileUtils.rm_rf(subject.id_path)
   end
 
   it "fallback to hostname when no name is provided" do
@@ -324,8 +325,10 @@ describe LogStash::Agent do
   context "metrics after config reloading" do
 
     let(:initial_generator_threshold) { 1000 }
-    let(:temporary_file) { Stud::Temporary.file.path }
-    let(:config_file_txt) { "input { generator { count => #{initial_generator_threshold*2} } } output { file { path => '#{temporary_file}'} }" }
+    let(:original_config_output) { Stud::Temporary.pathname }
+    let(:new_config_output) { Stud::Temporary.pathname }
+
+    let(:config_file_txt) { "input { generator { count => #{initial_generator_threshold*2} } } output { file { path => '#{original_config_output}'} }" }
 
     let(:agent_args) do
       {
@@ -336,15 +339,24 @@ describe LogStash::Agent do
 
     subject { described_class.new(agent_settings, default_source_loader) }
 
+    let(:agent_thread) do
+      # subject has to be called for the first time outside the thread because it could create a race condition
+      # with subsequent subject calls
+      s = subject
+      Thread.new { s.execute }
+    end
+
     before(:each) do
       @abort_on_exception = Thread.abort_on_exception
       Thread.abort_on_exception = true
 
-      @t = Thread.new { subject.execute }
+      agent_thread
 
       # wait for some events to reach the dummy_output
       Timeout.timeout(timeout) do
-        sleep(0.01) until IO.readlines(temporary_file).size > initial_generator_threshold
+        # wait for file existence otherwise it will raise exception on Windows
+        sleep(0.1) until ::File.exist?(original_config_output)
+        sleep(0.1) until IO.readlines(original_config_output).size > initial_generator_threshold
       end
 
       # write new config
@@ -353,10 +365,12 @@ describe LogStash::Agent do
 
     after :each do
       begin
+        Stud.stop!(agent_thread) rescue nil # it may be dead already
+        agent_thread.join
         subject.shutdown
-        Stud.stop!(@t) rescue nil # it may be dead already
-        @t.join
-        File.unlink(temporary_file)
+
+        FileUtils.rm(original_config_output)
+        FileUtils.rm(new_config_output) if File.exist?(new_config_output)
       rescue
           #don't care about errors here.
       ensure
@@ -366,21 +380,20 @@ describe LogStash::Agent do
 
     context "when reloading a good config" do
       let(:new_config_generator_counter) { 500 }
-      let(:new_file) { Stud::Temporary.file.path }
-      let(:new_config) { "input { generator { count => #{new_config_generator_counter} } } output { file { path => '#{new_file}'} }" }
+      let(:new_config) { "input { generator { count => #{new_config_generator_counter} } } output { file { path => '#{new_config_output}'} }" }
 
       before :each do
         subject.converge_state_and_update
         Timeout.timeout(timeout) do
-          sleep(0.01) while ::File.read(new_file).chomp.empty?
+          # wait for file existence otherwise it will raise exception on Windows
+          sleep(0.1) until ::File.exist?(new_config_output)
+          sleep(0.1) while ::File.read(new_config_output).chomp.empty?
         end
         # ensure the converge_state_and_update method has updated metrics by
         # invoking the mutex
         subject.running_pipelines?
       end
 
-      after(:each) { File.unlink(new_file) }
-
       it "resets the pipeline metric collector" do
         snapshot = subject.metric.collector.snapshot_metric
         value = snapshot.metric_store.get_with_path("/stats/pipelines")[:stats][:pipelines][:main][:events][:in].value
diff --git a/logstash-core/spec/logstash/api/modules/node_stats_spec.rb b/logstash-core/spec/logstash/api/modules/node_stats_spec.rb
index 340c680f3..729f9aee9 100644
--- a/logstash-core/spec/logstash/api/modules/node_stats_spec.rb
+++ b/logstash-core/spec/logstash/api/modules/node_stats_spec.rb
@@ -69,7 +69,7 @@ describe LogStash::Api::Modules::NodeStats do
       "cpu"=>{
         "total_in_millis"=>Numeric,
         "percent"=>Numeric,
-        "load_average" => { "1m" => Numeric }
+        # load_average is not supported on Windows, set it below
       }
     },
    "pipelines" => {
@@ -89,5 +89,9 @@ describe LogStash::Api::Modules::NodeStats do
    }
   }
 
+  unless LogStash::Environment.windows?
+    root_structure["process"]["cpu"]["load_average"] = { "1m" => Numeric }
+  end
+
   test_api_and_resources(root_structure)
 end
diff --git a/logstash-core/spec/logstash/config/source/local_spec.rb b/logstash-core/spec/logstash/config/source/local_spec.rb
index 9e3bf8659..2d5574839 100644
--- a/logstash-core/spec/logstash/config/source/local_spec.rb
+++ b/logstash-core/spec/logstash/config/source/local_spec.rb
@@ -79,7 +79,7 @@ describe LogStash::Config::Source::Local::ConfigPathLoader do
 
         parts.each do |part|
           basename = ::File.basename(part.id)
-          file_path = ::File.join(directory, basename)
+          file_path = ::File.expand_path(::File.join(directory, basename))
           content = files[basename]
           expect(part).to be_a_source_with_metadata("file", file_path, content)
         end
@@ -99,7 +99,8 @@ describe LogStash::Config::Source::Local::ConfigPathLoader do
       end
 
       it "raises an exception" do
-        expect { subject.read(file_path) }.to raise_error LogStash::ConfigLoadingError, /#{file_path}/
+        # check against base name because on Windows long paths are shrinked in the exception message
+        expect { subject.read(file_path) }.to raise_error LogStash::ConfigLoadingError, /.+#{::File.basename(file_path)}/
       end
     end
 
diff --git a/logstash-core/spec/logstash/pipeline_action/create_spec.rb b/logstash-core/spec/logstash/pipeline_action/create_spec.rb
index 90627a478..b59188130 100644
--- a/logstash-core/spec/logstash/pipeline_action/create_spec.rb
+++ b/logstash-core/spec/logstash/pipeline_action/create_spec.rb
@@ -19,7 +19,10 @@ describe LogStash::PipelineAction::Create do
   subject { described_class.new(pipeline_config, metric) }
 
   after do
-    pipelines.each { |_, pipeline| pipeline.shutdown }
+    pipelines.each do |_, pipeline| 
+      pipeline.shutdown 
+      pipeline.thread.join
+    end
   end
 
   it "returns the pipeline_id" do
diff --git a/logstash-core/spec/logstash/pipeline_action/reload_spec.rb b/logstash-core/spec/logstash/pipeline_action/reload_spec.rb
index fc2db33bb..60bb59686 100644
--- a/logstash-core/spec/logstash/pipeline_action/reload_spec.rb
+++ b/logstash-core/spec/logstash/pipeline_action/reload_spec.rb
@@ -22,7 +22,10 @@ describe LogStash::PipelineAction::Reload do
   end
 
   after do
-    pipelines.each { |_, pipeline| pipeline.shutdown }
+    pipelines.each do |_, pipeline| 
+      pipeline.shutdown
+      pipeline.thread.join
+    end
   end
 
   it "returns the pipeline_id" do
diff --git a/logstash-core/spec/logstash/pipeline_dlq_commit_spec.rb b/logstash-core/spec/logstash/pipeline_dlq_commit_spec.rb
index 83d1e5d16..c8643c528 100644
--- a/logstash-core/spec/logstash/pipeline_dlq_commit_spec.rb
+++ b/logstash-core/spec/logstash/pipeline_dlq_commit_spec.rb
@@ -67,7 +67,7 @@ describe LogStash::Pipeline do
   end
 
   after(:each) do
-    FileUtils.remove_entry pipeline_settings["path.dead_letter_queue"]
+    FileUtils.rm_rf(pipeline_settings["path.dead_letter_queue"])
   end
 
   context "dlq is enabled" do
@@ -85,6 +85,7 @@ describe LogStash::Pipeline do
       entry = dlq_reader.pollEntry(40)
       expect(entry).to_not be_nil
       expect(entry.reason).to eq("my reason")
+      subject.shutdown
     end
   end
 
@@ -101,6 +102,7 @@ describe LogStash::Pipeline do
       subject.run
       dlq_path = java.nio.file.Paths.get(pipeline_settings_obj.get("path.dead_letter_queue"), pipeline_id)
       expect(java.nio.file.Files.exists(dlq_path)).to eq(false)
+      subject.shutdown
     end
   end
 
diff --git a/logstash-core/spec/logstash/settings/writable_directory_spec.rb b/logstash-core/spec/logstash/settings/writable_directory_spec.rb
index 4463ca82d..be00ce9f0 100644
--- a/logstash-core/spec/logstash/settings/writable_directory_spec.rb
+++ b/logstash-core/spec/logstash/settings/writable_directory_spec.rb
@@ -3,17 +3,17 @@ require "spec_helper"
 require "logstash/settings"
 require "tmpdir"
 require "socket" # for UNIXSocket
+require "fileutils"
 
 describe LogStash::Setting::WritableDirectory do
-  let(:mode_rx) { 0555 }
   # linux is 108, Macos is 104, so use a safe value
   # Stud::Temporary.pathname, will exceed that size without adding anything
   let(:parent) { File.join(Dir.tmpdir, Time.now.to_f.to_s) }
   let(:path) { File.join(parent, "fancy") }
 
   before { Dir.mkdir(parent) }
-  after { Dir.exist?(path) && Dir.unlink(path) rescue nil }
-  after { Dir.unlink(parent) }
+  after { Dir.exist?(path) && FileUtils.rm_rf(path)}
+  after { FileUtils.rm_rf(parent) }
 
   shared_examples "failure" do
     before { subject.set(path) }
@@ -44,8 +44,9 @@ describe LogStash::Setting::WritableDirectory do
       end
 
       context "and the directory cannot be created" do
-        before { File.chmod(mode_rx, parent) }
         it "should fail" do
+          # using chmod does not work on Windows better mock and_raise("message")
+          expect(FileUtils).to receive(:mkdir_p).and_raise("foobar")
           expect { subject.value }.to raise_error
         end
       end
@@ -66,7 +67,8 @@ describe LogStash::Setting::WritableDirectory do
       end
 
       context "but is not writable" do
-        before { File.chmod(0, path) }
+        # chmod does not work on Windows, mock writable? instead
+        before { expect(File).to receive(:writable?).and_return(false) }
         it_behaves_like "failure"
       end
     end
@@ -84,12 +86,13 @@ describe LogStash::Setting::WritableDirectory do
         before { socket } # realize `socket` value
         after { socket.close }
         it_behaves_like "failure"
-      end
+      end unless LogStash::Environment.windows?
 
+      
       context "but is a symlink" do
-        before { File::symlink("whatever", path) }
+        before { FileUtils.symlink("whatever", path) }
         it_behaves_like "failure"
-      end
+      end unless LogStash::Environment.windows?
     end
 
     context "when the directory is missing" do
@@ -114,8 +117,8 @@ describe LogStash::Setting::WritableDirectory do
 
       context "and cannot be created" do
         before do
-          # Remove write permission on the parent
-          File.chmod(mode_rx, parent)
+          # chmod does not work on Windows, mock writable? instead
+          expect(File).to receive(:writable?).and_return(false)
         end
 
         it_behaves_like "failure"
diff --git a/spec/unit/plugin_manager/pack_fetch_strategy/uri_spec.rb b/spec/unit/plugin_manager/pack_fetch_strategy/uri_spec.rb
index 09effdb90..210b32d5b 100644
--- a/spec/unit/plugin_manager/pack_fetch_strategy/uri_spec.rb
+++ b/spec/unit/plugin_manager/pack_fetch_strategy/uri_spec.rb
@@ -32,10 +32,12 @@ describe LogStash::PluginManager::PackFetchStrategy::Uri do
     let(:temporary_file) do
       f = Stud::Temporary.file
       f.write("hola")
+      f.close
       f.path
     end
 
-    let(:plugin_path) { "file://#{temporary_file}" }
+    # Windows safe way to produce a file: URI.
+    let(:plugin_path) { URI.join("file:///" + File.absolute_path(temporary_file)).to_s }
 
     it "returns a `LocalInstaller`" do
       expect(subject.get_installer_for(plugin_path)).to be_kind_of(LogStash::PluginManager::PackInstaller::Local)
diff --git a/spec/unit/plugin_manager/prepare_offline_pack_spec.rb b/spec/unit/plugin_manager/prepare_offline_pack_spec.rb
index aa9376c91..9c55457d0 100644
--- a/spec/unit/plugin_manager/prepare_offline_pack_spec.rb
+++ b/spec/unit/plugin_manager/prepare_offline_pack_spec.rb
@@ -79,6 +79,10 @@ describe LogStash::PluginManager::PrepareOfflinePack do
         expect(LogStash::PluginManager::OfflinePluginPackager).not_to receive(:package).with(anything)
       end
 
+      after do
+        FileUtils.rm_rf(tmp_zip_file)
+      end
+
       it "fails to do any action" do
         expect { subject.run(cmd_args) }.to raise_error Clamp::ExecutionError, /you must specify a filename/
       end
@@ -101,13 +105,18 @@ describe LogStash::PluginManager::PrepareOfflinePack do
         FileUtils.touch(tmp_zip_file)
       end
 
+      after do
+        FileUtils.rm_f(tmp_zip_file)
+      end
+
       context "without `--overwrite`" do
         before do
           expect(LogStash::PluginManager::OfflinePluginPackager).not_to receive(:package).with(anything)
         end
 
         it "should fails" do
-          expect { subject.run(cmd_args) }.to raise_error Clamp::ExecutionError, /output file destination #{tmp_zip_file} already exist/
+          # ignore the first path part of tmp_zip_file because on Windows the long path is shrinked in the exception message 
+          expect { subject.run(cmd_args) }.to raise_error Clamp::ExecutionError, /output file destination .+#{::File.basename(tmp_zip_file)} already exist/
         end
       end
 
diff --git a/spec/unit/plugin_manager/utils/downloader_spec.rb b/spec/unit/plugin_manager/utils/downloader_spec.rb
index e08e731af..2f7a105eb 100644
--- a/spec/unit/plugin_manager/utils/downloader_spec.rb
+++ b/spec/unit/plugin_manager/utils/downloader_spec.rb
@@ -56,7 +56,7 @@ describe LogStash::PluginManager::Utils::Downloader do
       let(:temporary_path) { Stud::Temporary.pathname }
 
       before do
-        expect_any_instance_of(::File).to receive(:close).at_least(:twice).and_raise("Didn't work")
+        expect(Net::HTTP::Get).to receive(:new).once.and_raise("Didn't work")
         expect(Stud::Temporary).to receive(:pathname).and_return(temporary_path)
       end