diff --git a/Jenkinsfile b/Jenkinsfile
index 7f8400660..fd3a4511d 100644
--- a/Jenkinsfile
+++ b/Jenkinsfile
@@ -111,13 +111,132 @@ pipeline {
                 name: "Python",
                 steps: this
                 )
-              def mapPatallelTasks = pythonTasksGen.generateParallelTests()
-              parallel(mapPatallelTasks)
+              //def mapPatallelTasks = pythonTasksGen.generateParallelTests()
+              //parallel(mapPatallelTasks)
             }
           }
         }
       }
     }
+    stage('Parallel Windows Tests') {
+      parallel {
+        stage('Windows Py 2.7.16') {
+          agent { label 'windows-2019-immutable' }
+          options { skipDefaultCheckout() }
+          environment {
+            PATH = "C:\\Windows\\System32;${env.PATH}";
+          }
+          steps {
+            withGithubNotify(context: 'Test', tab: 'tests') {
+              deleteDir()
+              unstash "source"
+              dir("${BASE_DIR}") {
+                bat label: 'Execute Tests', script: ".\\tests\\scripts\\configure_windows_instance.bat 2.7.16 python27"
+                /*
+                bat label: 'Install Chocolatey', script: ".\\tests\\scripts\\install_chocolatey.bat"
+                bat label: 'Uninstall Python3', script: "choco uninstall python3"
+                bat label: 'Install Modules', script: ".\\tests\\scripts\\download_json_schema.bat"
+                bat label: 'Install Modules', script: ".\\tests\\scripts\\install_modules.bat python"
+                bat label: 'Execute Tests', script: "pytest"
+                */
+              }
+            }
+          }
+        }
+        stage('Windows Py 3.5.4') {
+          agent { label 'windows-2019-immutable' }
+          options { skipDefaultCheckout() }
+          environment {
+            PATH = "C:\\Windows\\System32;${env.PATH}";
+          }
+          steps {
+            withGithubNotify(context: 'Test', tab: 'tests') {
+              deleteDir()
+              unstash "source"
+              dir("${BASE_DIR}") {
+                bat label: 'Execute Tests', script: ".\\tests\\scripts\\configure_windows_instance.bat 3.5.4 python35"
+                /*
+                bat label: 'Install Chocolatey', script: ".\\tests\\scripts\\install_chocolatey.bat"
+                bat label: 'Install Python3.5', script: "./tests/scripts/install_python.bat 3.5.4"
+                bat label: 'Install Modules', script: "./tests/scripts/download_json_schema.bat"
+                bat label: 'Install Modules', script: "./tests/scripts/install_modules.bat py"
+                bat label: 'Execute Tests', script: "pytest"
+                */
+              }
+            }
+          }
+        }
+        stage('Windows Py 3.6.7') {
+          agent { label 'windows-2019-immutable' }
+          options { skipDefaultCheckout() }
+          environment {
+            PATH = "C:\\Windows\\System32;${env.PATH}";
+          }
+          steps {
+            withGithubNotify(context: 'Test', tab: 'tests') {
+              deleteDir()
+              unstash "source"
+              dir("${BASE_DIR}") {
+                bat label: 'Execute Tests', script: ".\\tests\\scripts\\configure_windows_instance.bat 3.6.7 python36"
+                /*
+                bat label: 'Install Chocolatey', script: ".\\tests\\scripts\\install_chocolatey.bat"
+                bat label: 'Install Python3.6', script: "./tests/scripts/install_python.bat 3.6.7"
+                bat label: 'Install Modules', script: "./tests/scripts/download_json_schema.bat"
+                bat label: 'Install Modules', script: "./tests/scripts/install_modules.bat py"
+                bat label: 'Execute Tests', script: "pytest"
+                */
+              }
+            }
+          }
+        }
+        stage('Windows Py 3.7.2') {
+          agent { label 'windows-2019-immutable' }
+          options { skipDefaultCheckout() }
+          environment {
+            PATH = "C:\\Windows\\System32;${env.PATH}";
+          }
+          steps {
+            withGithubNotify(context: 'Test', tab: 'tests') {
+              deleteDir()
+              unstash "source"
+              dir("${BASE_DIR}") {
+                bat label: 'Execute Tests', script: ".\\tests\\scripts\\configure_windows_instance.bat 3.7.2 py"
+                /*
+                bat label: 'Install Chocolatey', script: ".\\tests\\scripts\\install_chocolatey.bat"
+                bat label: 'Install Python3.7', script: "./tests/scripts/install_python.bat 3.7.2"
+                bat label: 'Install Modules', script: "./tests/scripts/download_json_schema.bat"
+                bat label: 'Install Modules', script: "./tests/scripts/install_modules.bat py"
+                bat label: 'Execute Tests', script: "pytest"
+                */
+              }
+            }
+          }
+        }
+        stage('Windows Py 3.8.1') {
+          agent { label 'windows-2019-immutable' }
+          options { skipDefaultCheckout() }
+          environment {
+            PATH = "C:\\Windows\\System32;${env.PATH}";
+          }
+          steps {
+            withGithubNotify(context: 'Test', tab: 'tests') {
+              deleteDir()
+              unstash "source"
+              dir("${BASE_DIR}") {
+                bat label: 'Execute Tests', script: ".\\tests\\scripts\\configure_windows_instance.bat 3.8.1 python38"
+                /*
+                bat label: 'Install Chocolatey', script: ".\\tests\\scripts\\install_chocolatey.bat"
+                bat label: 'Install Python3.7', script: "./tests/scripts/install_python.bat 3.8.1"
+                bat label: 'Install Modules', script: "./tests/scripts/download_json_schema.bat"
+                bat label: 'Install Modules', script: "./tests/scripts/install_modules.bat py"
+                bat label: 'Execute Tests', script: "pytest"
+                */
+                }
+              }
+            }
+        }
+      }
+    }
     stage('Building packages') {
       options { skipDefaultCheckout() }
       when {
diff --git a/tests/scripts/configure_windows_instance.bat b/tests/scripts/configure_windows_instance.bat
new file mode 100644
index 000000000..2842eaaa7
--- /dev/null
+++ b/tests/scripts/configure_windows_instance.bat
@@ -0,0 +1,8 @@
+.\tests\scripts\install_chocolatey.bat^
+    && refreshenv^
+    && .\tests\scripts\install_python.bat %1 %2^
+    && refreshenv^
+    && %2 -m pip install -r .\tests\requirements\requirements-base.txt^
+    && .\tests\scripts\download_json_schema.bat^
+    && .\tests\scripts\download_gherkin_features.bat^
+    && .\tests\scripts\execute_pytest_windows.bat %1 %2
\ No newline at end of file
diff --git a/tests/scripts/download_gherkin_features.bat b/tests/scripts/download_gherkin_features.bat
new file mode 100644
index 000000000..309d7e4eb
--- /dev/null
+++ b/tests/scripts/download_gherkin_features.bat
@@ -0,0 +1,6 @@
+mkdir .\tests\tempFeatures
+curl https://codeload.github.com/elastic/apm/zip/master -o .\tests\tempFeatures\features.zip
+7z x .\tests\tempFeatures\features.zip -o.\tests\tempFeatures *.feature -y -r
+mkdir .\tests\bdd\features
+xcopy .\tests\tempFeatures\apm-master\tests\agents\gherkin-specs\* .\tests\bdd\features /Y /S
+del .\tests\tempFeatures\ /F /Q /S
\ No newline at end of file
diff --git a/tests/scripts/download_json_schema.bat b/tests/scripts/download_json_schema.bat
new file mode 100644
index 000000000..1bfabac69
--- /dev/null
+++ b/tests/scripts/download_json_schema.bat
@@ -0,0 +1,6 @@
+mkdir .\tests\tempSchema
+curl https://codeload.github.com/elastic/apm-server/zip/master -o .\tests\tempSchema\master.zip
+7z x .\tests\tempSchema\master.zip -o.\tests\tempSchema *.json -y -r
+mkdir .\tests\.schemacache
+xcopy .\tests\tempSchema\apm-server-master\docs\spec\* .\tests\.schemacache /Y /S
+del .\tests\tempSchema\ /F /Q /S
\ No newline at end of file
diff --git a/tests/scripts/execute_pytest_windows.bat b/tests/scripts/execute_pytest_windows.bat
new file mode 100644
index 000000000..0d8758165
--- /dev/null
+++ b/tests/scripts/execute_pytest_windows.bat
@@ -0,0 +1,7 @@
+SETLOCAL EnableDelayedExpansion
+set pythonVersion=%1
+set pythonExecutable=%2
+set majorVersion=!pythonVersion:~0,1!
+set minorVersion=!pythonVersion:~2,1!
+if %majorVersion% EQU 2 (set pyArgs=--ignore-glob="*/py3_*.py" --ignore-glob="*/asyncio/*") else ( if %minorVersion% EQU 5 (set pyArgs=--ignore-glob="*/asyncio/*"))
+%pythonExecutable% -m pytest --cov --cov-report xml:coverage.xml %pyArgs%
\ No newline at end of file
diff --git a/tests/scripts/install_chocolatey.bat b/tests/scripts/install_chocolatey.bat
new file mode 100644
index 000000000..ac948a4bc
--- /dev/null
+++ b/tests/scripts/install_chocolatey.bat
@@ -0,0 +1 @@
+@"%SystemRoot%\System32\WindowsPowerShell\v1.0\powershell.exe" -NoProfile -InputFormat None -ExecutionPolicy Bypass -Command " [System.Net.ServicePointManager]::SecurityProtocol = 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))" && SET "PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin"
\ No newline at end of file
diff --git a/tests/scripts/install_modules.bat b/tests/scripts/install_modules.bat
new file mode 100644
index 000000000..44adebf19
--- /dev/null
+++ b/tests/scripts/install_modules.bat
@@ -0,0 +1,7 @@
+SETLOCAL EnableDelayedExpansion
+set pythonVersion=%1
+set pythonExecutable=%2
+set majorVersion=!pythonVersion:~0,1!
+echo !majorVersion!
+if %majorVersion% EQU 2 (!pythonExecutable! -m pip install -r .\tests\requirements\requirements-base.txt) else (!pythonExecutable! -m pip install -r .\tests\requirements\requirements-base.txt)
+SETLOCAL DisableDelayedExpansion
\ No newline at end of file
diff --git a/tests/scripts/install_python.bat b/tests/scripts/install_python.bat
new file mode 100644
index 000000000..5da019983
--- /dev/null
+++ b/tests/scripts/install_python.bat
@@ -0,0 +1,9 @@
+SETLOCAL EnableDelayedExpansion
+set pythonVersion=%1
+set pythonExecutable=%2
+set majorVersion=!pythonVersion:~0,1!
+set minorVersion=!pythonVersion:~2,1!
+if %majorVersion% EQU 3 (choco install python3 --version=%1 -y --force --allow-downgrade) else (choco install python2 -y --force)
+if %majorVersion% EQU 3 ( if %minorVersion% NEQ 7 (move c:\%pythonExecutable%\python.exe c:\%pythonExecutable%\%pythonExecutable%.exe)) else (move c:\%pythonExecutable%\python.exe c:\%pythonExecutable%\%pythonExecutable%.exe)
+SETLOCAL DisableDelayedExpansion
+