diff --git a/.buildkite/pipeline.yml b/.buildkite/pipeline.yml
index 919347b8750d..1f131194df2b 100644
--- a/.buildkite/pipeline.yml
+++ b/.buildkite/pipeline.yml
@@ -340,3 +340,29 @@ steps:
                     - BUILDKITE_PULL_REQUEST=${BUILDKITE_PULL_REQUEST}
                     - BUILDKITE_PULL_REQUEST_BASE_BRANCH=${BUILDKITE_PULL_REQUEST_BASE_BRANCH}
                     - GITHUB_PR_LABELS=${GITHUB_PR_LABELS}
+
+  - label: "Trigger Winlogbeat"
+    plugins:
+      - monorepo-diff#v1.0.1:
+          diff: "git diff --name-only origin/${GITHUB_PR_TARGET_BRANCH}...HEAD"
+          watch:
+            - path:
+                - winlogbeat/
+                - .buildkite/winlogbeat/pipeline.winlogbeat.yml
+                - .buildkite/scripts
+                - .buildkite/hooks
+                #OSS
+                - go.mod
+                - pytest.ini
+                - dev-tools/
+                - libbeat/
+                - testing/
+              config:
+                trigger: "beats-winlogbeat"
+                build:
+                  commit: "${BUILDKITE_COMMIT}"
+                  branch: "${BUILDKITE_BRANCH}"
+                  env:
+                    - BUILDKITE_PULL_REQUEST=${BUILDKITE_PULL_REQUEST}
+                    - BUILDKITE_PULL_REQUEST_BASE_BRANCH=${BUILDKITE_PULL_REQUEST_BASE_BRANCH}
+                    - GITHUB_PR_LABELS=${GITHUB_PR_LABELS}
diff --git a/.buildkite/scripts/common.sh b/.buildkite/scripts/common.sh
index ef4bd0d52bca..2b8471be6662 100755
--- a/.buildkite/scripts/common.sh
+++ b/.buildkite/scripts/common.sh
@@ -14,7 +14,6 @@ XPACK_MODULE_PATTERN="^x-pack\\/[a-z0-9]+beat\\/module\\/([^\\/]+)\\/.*"
 # define if needed run the whole pipeline for the particular beat
 [ -z "${run_filebeat+x}" ] && run_filebeat="$(buildkite-agent meta-data get run_filebeat --default "false")"
 [ -z "${run_packetbeat+x}" ] && run_packetbeat="$(buildkite-agent meta-data get run_packetbeat --default "false")"
-[ -z "${run_winlogbeat+x}" ] && run_winlogbeat="$(buildkite-agent meta-data get run_winlogbeat --default "false")"
 [ -z "${run_xpack_libbeat+x}" ] && run_xpack_libbeat="$(buildkite-agent meta-data get run_xpack_libbeat --default "false")"
 [ -z "${run_xpack_metricbeat+x}" ] && run_xpack_metricbeat="$(buildkite-agent meta-data get run_xpack_metricbeat --default "false")"
 [ -z "${run_xpack_packetbeat+x}" ] && run_xpack_packetbeat="$(buildkite-agent meta-data get run_xpack_packetbeat --default "false")"
diff --git a/.buildkite/winlogbeat/pipeline.winlogbeat.yml b/.buildkite/winlogbeat/pipeline.winlogbeat.yml
index 254370db030b..c71858b45b0a 100644
--- a/.buildkite/winlogbeat/pipeline.winlogbeat.yml
+++ b/.buildkite/winlogbeat/pipeline.winlogbeat.yml
@@ -2,10 +2,10 @@
 name: "beats-winlogbeat"
 
 env:
-  BEATS_PROJECT_NAME: "winlogbeat"
   GCP_DEFAULT_MACHINE_TYPE: "c2d-highcpu-8"
   GCP_HI_PERF_MACHINE_TYPE: "c2d-highcpu-16"
   GCP_WIN_MACHINE_TYPE: "n2-standard-8"
+
   IMAGE_UBUNTU_X86_64: "family/platform-ingest-beats-ubuntu-2204"
   IMAGE_WIN_10: "family/platform-ingest-beats-windows-10"
   IMAGE_WIN_11: "family/platform-ingest-beats-windows-11"
@@ -13,37 +13,141 @@ env:
   IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
-  #Packaging
-  PACKAGING_ARM_PLATFORMS: "linux/arm64"
-  PACKAGING_PLATFORMS: "+all linux/amd64 linux/arm64 windows/amd64 darwin/amd64 darwin/arm64"
-
-  #Deps
+  # Other deps
   ASDF_MAGE_VERSION: 1.15.0
 
 steps:
+  - group: "Winlogbeat Mandatory Tests"
+    key: "winlogbeat-mandatory-tests"
+
+    steps:
+      - label: ":ubuntu: Winlogbeat Crossccompile"
+        key: "mandatory-cross-compile"
+        command: "make -C winlogbeat crosscompile"
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_UBUNTU_X86_64}"
+          machineType: "${GCP_DEFAULT_MACHINE_TYPE}"
+        artifact_paths:
+          - "winlogbeat/build/*.xml"
+          - "winlogbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "Winlogbeat: Crosscompile"
+
+      - label: ":windows: Winlogbeat Win-2016 Unit Tests"
+        command: |
+          Set-Location -Path winlogbeat
+          mage build unitTest
+        key: "mandatory-win-2016-unit-tests"
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "winlogbeat/build/*.xml"
+          - "winlogbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "Winlogbeat: Win-2016 Unit Tests"
+
+      - label: ":windows: Winlogbeat Win-2019 Unit Tests"
+        command: |
+          Set-Location -Path winlogbeat
+          mage build unitTest
+        key: "mandatory-win-2019-unit-tests"
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "winlogbeat/build/*.xml"
+          - "winlogbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "Winlogbeat: Win-2019 Unit Tests"
 
-  - input: "Input Parameters"
-    key: "input-run-all-stages"
-    fields:
-    - select: "Winlogbeat - run_winlogbeat"
-      key: "run_winlogbeat"
-      options:
-        - label: "True"
-          value: "true"
-        - label: "False"
-          value: "false"
-      default: "false"
-    if: "build.source == 'ui'"
+      - label: ":windows: Winlogbeat Win-2022 Unit Tests"
+        command: |
+          Set-Location -Path winlogbeat
+          mage build unitTest
+        key: "mandatory-win-2022-unit-tests"
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2022}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "winlogbeat/build/*.xml"
+          - "winlogbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "Winlogbeat: Win-2022 Unit Tests"
+
+  - group: "Winlogbeat Extended Windows Tests"
+    key: "winlogbeat-extended-win-tests"
+    if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*[Ww]indows.*/
+
+    steps:
+      - label: ":windows: Winlogbeat Win-10 Unit Tests"
+        command: |
+          Set-Location -Path winlogbeat
+          mage build unitTest
+        key: "extended-win-10-unit-tests"
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_10}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "winlogbeat/build/*.xml"
+          - "winlogbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "Winlogbeat: Win-10 Unit Tests"
+
+      - label: ":windows: Winlogbeat Win-11 Unit Tests"
+        command: |
+          Set-Location -Path winlogbeat
+          mage build unitTest
+        key: "extended-win-11-unit-tests"
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_11}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "winlogbeat/build/*.xml"
+          - "winlogbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "Winlogbeat: Win-11 Unit Tests"
 
   - wait: ~
-    if: "build.source == 'ui'"
-    allow_dependency_failure: false
-
-  - label: ":linux: Load dynamic winlogbeat pipeline"
-    key: "winlogbeat-pipeline"
-    command: ".buildkite/scripts/generate_winlogbeat_pipeline.sh"
-    agents:
-      image: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci:latest"
-    notify:
-      - github_commit_status:
-          context: "${BEATS_PROJECT_NAME}: Load dynamic pipeline's steps"
+    if: build.env("BUILDKITE_PULL_REQUEST") != "false"
+    depends_on: "winlogbeat-mandatory-tests"
+
+  - group: "Winlogbeat Packaging"
+    key: "winlogbeat-packaging"
+    steps:
+      - label: ":ubuntu: Winlogbeat Packaging Ubuntu x86_64"
+        key: "packaging-linux"
+        command: |
+          cd winlogbeat
+          mage package
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_UBUNTU_X86_64}"
+          machineType: "${GCP_HI_PERF_MACHINE_TYPE}"
+        env:
+          PLATFORMS: "+all linux/amd64 linux/arm64 windows/amd64 darwin/amd64 darwin/arm64"
+        notify:
+          - github_commit_status:
+              context: "Winlogbeat: Packaging Ubuntu x86_64"