diff --git a/.buildkite/auditbeat/auditbeat-pipeline.yml b/.buildkite/auditbeat/auditbeat-pipeline.yml
index 300e9ac0e260..47a00b2c96d4 100644
--- a/.buildkite/auditbeat/auditbeat-pipeline.yml
+++ b/.buildkite/auditbeat/auditbeat-pipeline.yml
@@ -19,6 +19,8 @@ env:
   IMAGE_UBUNTU_2404_ARM64: "platform-ingest-beats-ubuntu-2404-aarch64"
   IMAGE_WIN_10: "family/platform-ingest-beats-windows-10"
   IMAGE_WIN_11: "family/platform-ingest-beats-windows-11"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -128,6 +130,32 @@ steps:
           - github_commit_status:
               context: "auditbeat: RHEL9 Unit Tests"
 
+      - label: ":windows: Auditbeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path auditbeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 200
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "auditbeat/build/*.xml"
+          - "auditbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "auditbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "auditbeat: Win 2016 Unit Tests"
+
       - label: ":windows: Auditbeat: Win 2022 Unit Tests"
         command: |
           Set-Location -Path auditbeat
@@ -329,6 +357,33 @@ steps:
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*[Ww]indows.*/
 
     steps:
+      - label: ":windows: Auditbeat: Win 2019 Unit Tests"
+        key: "auditbeat-extended-win-2019-unit-tests"
+        command: |
+          Set-Location -Path auditbeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "auditbeat/build/*.xml"
+          - "auditbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "auditbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "auditbeat: Win 2019 Unit Tests"
+
       - label: ":windows: Auditbeat: Win 10 Unit Tests"
         key: "auditbeat-extended-win-10-unit-tests"
         command: |
diff --git a/.buildkite/filebeat/filebeat-pipeline.yml b/.buildkite/filebeat/filebeat-pipeline.yml
index 6d4eb41f50db..92b007cfdf38 100644
--- a/.buildkite/filebeat/filebeat-pipeline.yml
+++ b/.buildkite/filebeat/filebeat-pipeline.yml
@@ -14,6 +14,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -151,6 +153,33 @@ steps:
           - github_commit_status:
               context: "filebeat: Python Integration Tests"
 
+      - label: ":windows: Filebeat: Win 2016 Unit Tests"
+        key: "windows-2016-unit-tests"
+        command: |
+          Set-Location -Path filebeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 200
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "filebeat/build/*.xml"
+          - "filebeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "filebeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "filebeat: Win 2016 Unit Tests"
+
       - label: ":windows: Filebeat: Win 2022 Unit Tests"
         key: "windows-2022-unit-tests"
         command: |
@@ -274,6 +303,33 @@ steps:
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*[Ww]indows.*/
 
     steps:
+      - label: ":windows: Filebeat: Win 2019 Unit Tests"
+        key: "windows-extended-2019"
+        command: |
+          Set-Location -Path filebeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 200
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "filebeat/build/*.xml"
+          - "filebeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "filebeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "filebeat: Win 2019 Unit Tests"
+
       - label: ":windows: Filebeat: Win 11 Unit Tests"
         key: "windows-extended-11"
         command: |
diff --git a/.buildkite/heartbeat/heartbeat-pipeline.yml b/.buildkite/heartbeat/heartbeat-pipeline.yml
index ae532e332865..13b0c8035b4f 100644
--- a/.buildkite/heartbeat/heartbeat-pipeline.yml
+++ b/.buildkite/heartbeat/heartbeat-pipeline.yml
@@ -14,6 +14,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -111,6 +113,26 @@ steps:
           - github_commit_status:
               context: "heartbeat: RHEL9 Unit Tests"
 
+      - label: ":windows: Heartbeat: Win 2016 Unit Tests"
+        key: "windows-2016"
+        command: |
+          Set-Location -Path heartbeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "heartbeat/build/*.xml"
+          - "heartbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "heartbeat: Win 2016 Unit Tests"
+
       - label: ":windows: Heartbeat: Win 2022 Unit Test"
         key: "windows-2022"
         command: |
@@ -245,6 +267,26 @@ steps:
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*[Ww]indows.*/
 
     steps:
+      - label: ":windows: Heartbeat: Win 2019 Unit Tests"
+        key: "heartbeat-win-extended-2019"
+        command: |
+          Set-Location -Path heartbeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "heartbeat/build/*.xml"
+          - "heartbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "heartbeat: Win 2019 Unit Tests"
+
       - label: ":windows: Heartbeat: Win 11 Unit Tests"
         key: "heartbeat-windows-extended-11"
         command: |
diff --git a/.buildkite/metricbeat/pipeline.yml b/.buildkite/metricbeat/pipeline.yml
index 814f079671ac..674e55c5207f 100644
--- a/.buildkite/metricbeat/pipeline.yml
+++ b/.buildkite/metricbeat/pipeline.yml
@@ -14,6 +14,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -177,6 +179,33 @@ steps:
           - github_commit_status:
               context: "metricbeat: Crosscompile"
 
+      - label: ":windows: Metricbeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path metricbeat
+          mage build unitTest
+        key: "mandatory-win-2016-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "metricbeat/build/*.xml"
+          - "metricbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "metricbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "metricbeat: Win 2016 Unit Tests"
+
       - label: ":windows: Metricbeat: Win 2022 Unit Tests"
         command: |
           Set-Location -Path metricbeat
@@ -263,6 +292,33 @@ steps:
           - github_commit_status:
               context: "metricbeat: Win 11 Unit Tests"
 
+      - label: ":windows: Metricbeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path metricbeat
+          mage build unitTest
+        key: "extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "metricbeat/build/*.xml"
+          - "metricbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "metricbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "metricbeat: Win 2019 Unit Tests"
+
   - group: "Extended Tests"
     key: "metricbeat-extended-tests"
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*macOS.*/
diff --git a/.buildkite/packetbeat/pipeline.packetbeat.yml b/.buildkite/packetbeat/pipeline.packetbeat.yml
index 27a117a13ff4..31cdecd4ae01 100644
--- a/.buildkite/packetbeat/pipeline.packetbeat.yml
+++ b/.buildkite/packetbeat/pipeline.packetbeat.yml
@@ -15,6 +15,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -122,6 +124,32 @@ steps:
           - github_commit_status:
               context: "packetbeat: RHEL9 Unit Tests"
 
+      - label: ":windows: Packetbeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path packetbeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "packetbeat/build/*.xml"
+          - "packetbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "packetbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "packetbeat: Win 2016 Unit Tests"
+
       - label: ":windows: Packetbeat: Win 2022 Unit Tests"
         command: |
           Set-Location -Path packetbeat
@@ -206,6 +234,33 @@ steps:
           - github_commit_status:
               context: "packetbeat: Win 11 Unit Tests"
 
+      - label: ":windows: Packetbeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path packetbeat
+          mage build unitTest
+        key: "extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "packetbeat/build/*.xml"
+          - "packetbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "packetbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "packetbeat: Win 2019 Unit Tests"
+
   - group: "Extended Tests"
     key: "extended-tests"
 
diff --git a/.buildkite/winlogbeat/pipeline.winlogbeat.yml b/.buildkite/winlogbeat/pipeline.winlogbeat.yml
index bce08c5204a1..d8986a72a54e 100644
--- a/.buildkite/winlogbeat/pipeline.winlogbeat.yml
+++ b/.buildkite/winlogbeat/pipeline.winlogbeat.yml
@@ -9,6 +9,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -82,6 +84,48 @@ steps:
           - 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"
+        retry:
+          automatic:
+            - limit: 1
+        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"
+        retry:
+          automatic:
+            - limit: 1
+        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"
+
       - label: ":windows: Winlogbeat: Win 2022 Unit Tests"
         command: |
           Set-Location -Path winlogbeat
diff --git a/.buildkite/x-pack/pipeline.xpack.auditbeat.yml b/.buildkite/x-pack/pipeline.xpack.auditbeat.yml
index c9a9f9ac2699..cca156252436 100644
--- a/.buildkite/x-pack/pipeline.xpack.auditbeat.yml
+++ b/.buildkite/x-pack/pipeline.xpack.auditbeat.yml
@@ -15,6 +15,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -154,11 +156,65 @@ steps:
           - github_commit_status:
               context: "x-pack/auditbeat: Win 2022 Unit Tests"
 
+      - label: ":windows: x-pack/auditbeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/auditbeat
+          mage build unitTest
+        key: "mandatory-win-2016-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/auditbeat/build/*.xml"
+          - "x-pack/auditbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/auditbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/auditbeat: Win 2016 Unit Tests"
+
   - group: "Extended Windows Tests"
     key: "x-pack-auditbeat-extended-win-tests"
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*[Ww]indows.*/
 
     steps:
+      - label: ":windows: x-pack/auditbeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/auditbeat
+          mage build unitTest
+        key: "extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/auditbeat/build/*.xml"
+          - "x-pack/auditbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/auditbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/auditbeat: Win 2019 Unit Tests"
+
       - label: ":windows: x-pack/auditbeat: Win 10 Unit Tests"
         command: |
           Set-Location -Path x-pack/auditbeat
diff --git a/.buildkite/x-pack/pipeline.xpack.filebeat.yml b/.buildkite/x-pack/pipeline.xpack.filebeat.yml
index 77178201dd10..2dc0c8186543 100644
--- a/.buildkite/x-pack/pipeline.xpack.filebeat.yml
+++ b/.buildkite/x-pack/pipeline.xpack.filebeat.yml
@@ -14,6 +14,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -176,11 +178,65 @@ steps:
           - github_commit_status:
               context: "x-pack/filebeat: Win 2022 Unit Tests"
 
+      - label: ":windows: x-pack/filebeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/filebeat
+          mage build unitTest
+        key: "x-pack-filebeat-mandatory-win-2016-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/filebeat/build/*.xml"
+          - "x-pack/filebeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/filebeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/filebeat: Win 2016 Unit Tests"
+
   - group: "Extended Windows Tests"
     key: "x-pack-filebeat-extended-win-tests"
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*[Ww]indows.*/
 
     steps:
+      - label: ":windows: x-pack/filebeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/filebeat
+          mage build unitTest
+        key: "x-pack-filebeat-extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/filebeat/build/*.xml"
+          - "x-pack/filebeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/filebeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/filebeat: Win 2019 Unit Tests"
+
       - label: ":windows: x-pack/filebeat: Win 10 Unit Tests"
         command: |
           Set-Location -Path x-pack/filebeat
diff --git a/.buildkite/x-pack/pipeline.xpack.heartbeat.yml b/.buildkite/x-pack/pipeline.xpack.heartbeat.yml
index 1b49d78cac4c..839bfc8a35a4 100644
--- a/.buildkite/x-pack/pipeline.xpack.heartbeat.yml
+++ b/.buildkite/x-pack/pipeline.xpack.heartbeat.yml
@@ -15,6 +15,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -136,6 +138,33 @@ steps:
           - github_commit_status:
               context: "x-pack/heartbeat: Go Integration Tests"
 
+      - label: ":windows: x-pack/heartbeat: Win 2016 Unit Tests"
+        key: "mandatory-win-2016-unit-tests"
+        command: |
+          Set-Location -Path x-pack/heartbeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/heartbeat/build/*.xml"
+          - "x-pack/heartbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/heartbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/heartbeat: Win 2016 Unit Tests"
+
       - label: ":windows: x-pack/heartbeat: Win 2022 Unit Tests"
         key: "mandatory-win-2022-unit-tests"
         command: |
@@ -222,6 +251,33 @@ steps:
           - github_commit_status:
               context: "x-pack/heartbeat: Win 11 Unit Tests"
 
+      - label: ":windows: x-pack/heartbeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/heartbeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        key: "extended-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:
+          - "x-pack/heartbeat/build/*.xml"
+          - "x-pack/heartbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/heartbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/heartbeat: Win 2019 Unit Tests"
+
   - group: "Extended Tests"
     key: "x-pack-heartbeat-extended-tests-macos"
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*macOS.*/
diff --git a/.buildkite/x-pack/pipeline.xpack.libbeat.yml b/.buildkite/x-pack/pipeline.xpack.libbeat.yml
index b0fc9c0fd1d0..431ae1aed819 100644
--- a/.buildkite/x-pack/pipeline.xpack.libbeat.yml
+++ b/.buildkite/x-pack/pipeline.xpack.libbeat.yml
@@ -8,6 +8,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -122,6 +124,27 @@ steps:
           - github_commit_status:
               context: "x-pack/libbeat: Python Integration Tests"
 
+      - label: ":windows: x-pack/libbeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/libbeat
+          mage -w reader\etw build goUnitTest
+        key: "mandatory-win-2016-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/libbeat/build/*.xml"
+          - "x-pack/libbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "x-pack/libbeat: Win 2016 Unit Tests"
+
       - label: ":windows: x-pack/libbeat: Win 2022 Unit Tests"
         command: |
           Set-Location -Path x-pack/libbeat
@@ -190,6 +213,27 @@ steps:
           - github_commit_status:
               context: "x-pack/libbeat: Win 11 Unit Tests"
 
+      - label: ":windows: x-pack/libbeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/libbeat
+          mage -w reader\etw build goUnitTest
+        key: "extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/libbeat/build/*.xml"
+          - "x-pack/libbeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "x-pack/libbeat: Win 2019 Unit Tests"
+
   - group: "Extended Tests"
     key: "x-pack-libbeat-extended-tests-linux-arm"
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*arm.*/
diff --git a/.buildkite/x-pack/pipeline.xpack.metricbeat.yml b/.buildkite/x-pack/pipeline.xpack.metricbeat.yml
index 4b3ed75b7a36..a074c681a968 100644
--- a/.buildkite/x-pack/pipeline.xpack.metricbeat.yml
+++ b/.buildkite/x-pack/pipeline.xpack.metricbeat.yml
@@ -14,6 +14,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -154,6 +156,33 @@ steps:
           - github_commit_status:
               context: "x-pack/metricbeat: Python Integration Tests (Module)"
 
+      - label: ":windows: x-pack/metricbeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/metricbeat
+          mage build unitTest
+        key: "mandatory-win-2016-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/metricbeat/build/*.xml"
+          - "x-pack/metricbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/metricbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/metricbeat: Win 2016 Unit Tests"
+
       - label: ":windows: x-pack/metricbeat: Win 2022 Unit Tests"
         command: |
           Set-Location -Path x-pack/metricbeat
@@ -240,6 +269,33 @@ steps:
           - github_commit_status:
               context: "x-pack/metricbeat: Win 11 Unit Tests"
 
+      - label: ":windows: x-pack/metricbeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/metricbeat
+          mage build unitTest
+        key: "extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/metricbeat/build/*.xml"
+          - "x-pack/metricbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/metricbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/metricbeat: Win 2019 Unit Tests"
+
   - group: "Extended Tests"
     key: "x-pack-metricbeat-extended-tests"
     if: build.env("BUILDKITE_PULL_REQUEST") == "false"  || build.env("GITHUB_PR_LABELS") =~ /.*(macOS|aws).*/
diff --git a/.buildkite/x-pack/pipeline.xpack.osquerybeat.yml b/.buildkite/x-pack/pipeline.xpack.osquerybeat.yml
index fae69c6cf093..c06f473c000c 100644
--- a/.buildkite/x-pack/pipeline.xpack.osquerybeat.yml
+++ b/.buildkite/x-pack/pipeline.xpack.osquerybeat.yml
@@ -11,6 +11,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -108,6 +110,27 @@ steps:
           - github_commit_status:
               context: "x-pack/osquerybeat: Go Integration Tests"
 
+      - label: ":windows: x-pack/osquerybeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/osquerybeat
+          mage build unitTest
+        key: "mandatory-win-2016-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/osquerybeat/build/*.xml"
+          - "x-pack/osquerybeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "x-pack/osquerybeat: Win 2016 Unit Tests"
+
       - label: ":windows: x-pack/osquerybeat: Win 2022 Unit Tests"
         command: |
           Set-Location -Path x-pack/osquerybeat
@@ -176,6 +199,27 @@ steps:
           - github_commit_status:
               context: "x-pack/osquerybeat: Win 11 Unit Tests"
 
+      - label: ":windows: x-pack/osquerybeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/osquerybeat
+          mage build unitTest
+        key: "extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/osquerybeat/build/*.xml"
+          - "x-pack/osquerybeat/build/*.json"
+        notify:
+          - github_commit_status:
+              context: "x-pack/osquerybeat: Win 2019 Unit Tests"
+
   - group: "Extended Tests"
     key: "x-pack-osquerybeat-extended-tests"
     if: build.env("BUILDKITE_PULL_REQUEST") == "false" || build.env("GITHUB_PR_LABELS") =~ /.*macOS.*/
diff --git a/.buildkite/x-pack/pipeline.xpack.packetbeat.yml b/.buildkite/x-pack/pipeline.xpack.packetbeat.yml
index a4503316bfb9..1620bc2320ae 100644
--- a/.buildkite/x-pack/pipeline.xpack.packetbeat.yml
+++ b/.buildkite/x-pack/pipeline.xpack.packetbeat.yml
@@ -15,6 +15,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
 
   IMAGE_BEATS_WITH_HOOKS_LATEST: "docker.elastic.co/ci-agent-images/platform-ingest/buildkite-agent-beats-ci-with-hooks:latest"
@@ -149,6 +151,33 @@ steps:
           - github_commit_status:
               context: "x-pack/packetbeat: RHEL9 Unit Tests"
 
+      - label: ":windows: x-pack/packetbeat: Win 2016 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/packetbeat
+          mage build unitTest
+        key: "mandatory-win-2016-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/packetbeat/build/*.xml"
+          - "x-pack/packetbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/packetbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/packetbeat: Win 2016 Unit Tests"
+
       - label: ":windows: x-pack/packetbeat: Win 2022 Unit Tests"
         command: |
           Set-Location -Path x-pack/packetbeat
@@ -263,6 +292,33 @@ steps:
           - github_commit_status:
               context: "x-pack/packetbeat: Win 11 Unit Tests"
 
+      - label: ":windows: x-pack/packetbeat: Win 2019 Unit Tests"
+        command: |
+          Set-Location -Path x-pack/packetbeat
+          mage build unitTest
+        key: "extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/packetbeat/build/*.xml"
+          - "x-pack/packetbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/packetbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/packetbeat: Win 2019 Unit Tests"
+
       - label: ":windows: x-pack/packetbeat: Win 10 System Tests"
         key: "extended-win-10-system-tests"
         command: |
diff --git a/.buildkite/x-pack/pipeline.xpack.winlogbeat.yml b/.buildkite/x-pack/pipeline.xpack.winlogbeat.yml
index e1cd5c953a54..d0ffd9fa89c9 100644
--- a/.buildkite/x-pack/pipeline.xpack.winlogbeat.yml
+++ b/.buildkite/x-pack/pipeline.xpack.winlogbeat.yml
@@ -5,6 +5,8 @@ env:
   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"
+  IMAGE_WIN_2016: "family/platform-ingest-beats-windows-2016"
+  IMAGE_WIN_2019: "family/platform-ingest-beats-windows-2019"
   IMAGE_WIN_2022: "family/platform-ingest-beats-windows-2022"
   GCP_WIN_MACHINE_TYPE: "n2-standard-8"
   GCP_HI_PERF_MACHINE_TYPE: "c2d-highcpu-16"
@@ -60,6 +62,62 @@ steps:
     key: "x-pack-winlogbeat-mandatory-tests"
 
     steps:
+      - label: ":windows: x-pack/winlogbeat Win 2019 Unit Tests"
+        key: "mandatory-win-2019-unit-tests"
+        command: |
+          .buildkite/scripts/install_sysmon.ps1
+          Set-Location -Path x-pack/winlogbeat
+          mage build unitTest
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/winlogbeat/build/*.xml"
+          - "x-pack/winlogbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/winlogbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/winlogbeat Win 2019 Unit Tests"
+
+      - label: ":windows: x-pack/winlogbeat: Win 2016 Unit Tests"
+        command: |
+          .buildkite/scripts/install_sysmon.ps1
+          Set-Location -Path x-pack/winlogbeat
+          mage build unitTest
+        key: "mandatory-win-2016-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2016}"
+          machine_type: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/winlogbeat/build/*.xml"
+          - "x-pack/winlogbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/winlogbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/winlogbeat: Win 2016 Unit Tests"
+
       - label: ":windows: x-pack/winlogbeat: Win 2022 Unit Tests"
         command: |
           .buildkite/scripts/install_sysmon.ps1
@@ -149,6 +207,34 @@ steps:
           - github_commit_status:
               context: "x-pack/winlogbeat: Win 11 Unit Tests"
 
+      - label: ":windows: x-pack/winlogbeat: Win 2019 Unit Tests"
+        command: |
+          .buildkite/scripts/install_sysmon.ps1
+          Set-Location -Path x-pack/winlogbeat
+          mage build unitTest
+        key: "extended-win-2019-unit-tests"
+        retry:
+          automatic:
+            - limit: 1
+        agents:
+          provider: "gcp"
+          image: "${IMAGE_WIN_2019}"
+          machineType: "${GCP_WIN_MACHINE_TYPE}"
+          disk_size: 100
+          disk_type: "pd-ssd"
+        artifact_paths:
+          - "x-pack/winlogbeat/build/*.xml"
+          - "x-pack/winlogbeat/build/*.json"
+        plugins:
+          - test-collector#v1.10.2:
+              files: "x-pack/winlogbeat/build/TEST-*.xml"
+              format: "junit"
+              branches: "main"
+              debug: true
+        notify:
+          - github_commit_status:
+              context: "x-pack/winlogbeat: Win 2019 Unit Tests"
+
   - wait: ~
     # with PRs, we want to run packaging only if mandatory tests succeed
     # for other cases, e.g. merge commits, we want to run packaging (and publish) independently of other tests