diff --git a/.gitlab/ci/build.yml b/.gitlab/ci/build.yml
index abb077d38a..6cbfa370ca 100644
--- a/.gitlab/ci/build.yml
+++ b/.gitlab/ci/build.yml
@@ -550,6 +550,38 @@ pytest_build_system_macos:
     reports:
       junit: XUNIT_RESULT.xml
 
+.test_build_system_template_win:
+  stage: host_test
+  variables:
+  # Enable ccache for all build jobs. See configure_ci_environment.sh for more ccache related settings.
+    IDF_CCACHE_ENABLE: "1"
+    PYTHONPATH: "$PYTHONPATH;$IDF_PATH\\tools;$IDF_PATH\\tools\\esp_app_trace;$IDF_PATH\\components\\partition_table;$IDF_PATH\\tools\\ci\\python_packages"
+  before_script: []
+  after_script: []
+  timeout: 4 hours
+  script:
+    - .\install.ps1 --enable-ci --enable-pytest
+    - . .\export.ps1
+    - python "${SUBMODULE_FETCH_TOOL}" -s "all"
+    - cd ${IDF_PATH}\tools\test_build_system
+    - pytest --junitxml=${CI_PROJECT_DIR}\XUNIT_RESULT.xml
+
+pytest_build_system_win:
+  extends:
+    - .test_build_system_template_win
+    - .rules:test:windows_pytest_build_system
+  needs: []
+  tags:
+    - windows-target
+  artifacts:
+    paths:
+      - XUNIT_RESULT.xml
+      - test_build_system
+    when: always
+    expire_in: 2 days
+    reports:
+      junit: XUNIT_RESULT.xml
+
 build_docker:
   extends:
     - .before_script:minimal
diff --git a/.gitlab/ci/dependencies/dependencies.yml b/.gitlab/ci/dependencies/dependencies.yml
index 5905f5be9f..e0e0face19 100644
--- a/.gitlab/ci/dependencies/dependencies.yml
+++ b/.gitlab/ci/dependencies/dependencies.yml
@@ -175,6 +175,12 @@
   patterns:
     - submodule
 
+"test:windows_pytest_build_system":
+  labels:
+    - windows
+  specific_rules:
+    - if-schedule-test-build-system-windows
+
 #################################
 # Triggered Only By Labels Jobs #
 #################################
diff --git a/.gitlab/ci/rules.yml b/.gitlab/ci/rules.yml
index 3fbbeeceeb..f3d65e59ec 100644
--- a/.gitlab/ci/rules.yml
+++ b/.gitlab/ci/rules.yml
@@ -350,6 +350,9 @@
 .if-schedule: &if-schedule
   if: '$CI_PIPELINE_SOURCE == "schedule"'
 
+.if-schedule-test-build-system-windows: &if-schedule-test-build-system-windows
+  if: '$CI_PIPELINE_SOURCE == "schedule" && $SCHEDULED_BUILD_SYSTEM_TEST_WIN == "true"'
+
 .if-trigger: &if-trigger
   if: '$CI_PIPELINE_SOURCE == "trigger"'
 
@@ -561,6 +564,9 @@
 .if-label-target_test: &if-label-target_test
   if: '$BOT_LABEL_TARGET_TEST || $CI_MERGE_REQUEST_LABELS =~ /^(?:[^,\n\r]+,)*target_test(?:,[^,\n\r]+)*$/i'
 
+.if-label-windows: &if-label-windows
+  if: '$BOT_LABEL_WINDOWS || $CI_MERGE_REQUEST_LABELS =~ /^(?:[^,\n\r]+,)*windows(?:,[^,\n\r]+)*$/i'
+
 .rules:build:
   rules:
     - <<: *if-revert-branch
@@ -2574,3 +2580,13 @@
     - <<: *if-label-submodule
     - <<: *if-dev-push
       changes: *patterns-submodule
+
+.rules:test:windows_pytest_build_system:
+  rules:
+    - <<: *if-revert-branch
+      when: never
+    - <<: *if-protected
+    - <<: *if-label-build-only
+      when: never
+    - <<: *if-schedule-test-build-system-windows
+    - <<: *if-label-windows
diff --git a/tools/ci/python_packages/gitlab_api.py b/tools/ci/python_packages/gitlab_api.py
index b9f3d326ce..1482ddd52f 100644
--- a/tools/ci/python_packages/gitlab_api.py
+++ b/tools/ci/python_packages/gitlab_api.py
@@ -4,6 +4,7 @@ import argparse
 import logging
 import os
 import re
+import sys
 import tarfile
 import tempfile
 import time
@@ -230,9 +231,19 @@ class Gitlab(object):
 
     @staticmethod
     def decompress_archive(path: str, destination: str) -> str:
-        with tarfile.open(path, 'r') as archive_file:
-            root_name = archive_file.getnames()[0]
-            archive_file.extractall(destination)
+        full_destination = os.path.abspath(destination)
+        # By default max path lenght is set to 260 characters
+        # Prefix `\\?\` extends it to 32,767 characters
+        if sys.platform == 'win32':
+            full_destination = '\\\\?\\' + full_destination
+
+        try:
+            with tarfile.open(path, 'r') as archive_file:
+                root_name = archive_file.getnames()[0]
+                archive_file.extractall(full_destination)
+        except tarfile.TarError as e:
+            logging.error(f'Error while decompressing archive {path}')
+            raise e
 
         return os.path.join(os.path.realpath(destination), root_name)