diff --git a/.buildkite/pipelines/periodic-packaging.template.yml b/.buildkite/pipelines/periodic-packaging.template.yml
index 87a7142929516..1a1e46d55f7a4 100644
--- a/.buildkite/pipelines/periodic-packaging.template.yml
+++ b/.buildkite/pipelines/periodic-packaging.template.yml
@@ -41,8 +41,6 @@ steps:
         matrix:
           setup:
             image:
-              - windows-2016
-              - windows-2019
               - windows-2022
         agents:
           provider: gcp
diff --git a/.buildkite/pipelines/periodic-packaging.yml b/.buildkite/pipelines/periodic-packaging.yml
index 6a2c6e0f59a2d..610eb018c575c 100644
--- a/.buildkite/pipelines/periodic-packaging.yml
+++ b/.buildkite/pipelines/periodic-packaging.yml
@@ -346,8 +346,6 @@ steps:
         matrix:
           setup:
             image:
-              - windows-2016
-              - windows-2019
               - windows-2022
         agents:
           provider: gcp
diff --git a/.buildkite/pipelines/periodic-platform-support.yml b/.buildkite/pipelines/periodic-platform-support.yml
index 848e84221668e..79e5a2e8dcdbb 100644
--- a/.buildkite/pipelines/periodic-platform-support.yml
+++ b/.buildkite/pipelines/periodic-platform-support.yml
@@ -39,8 +39,6 @@ steps:
         matrix:
           setup:
             image:
-              - windows-2016
-              - windows-2019
               - windows-2022
             GRADLE_TASK:
               - checkPart1
diff --git a/.buildkite/pipelines/pull-request/packaging-tests-windows-sample.yml b/.buildkite/pipelines/pull-request/packaging-tests-windows-sample.yml
index bcf38f51f4a66..6e8fec65f75a5 100644
--- a/.buildkite/pipelines/pull-request/packaging-tests-windows-sample.yml
+++ b/.buildkite/pipelines/pull-request/packaging-tests-windows-sample.yml
@@ -12,7 +12,7 @@ steps:
         matrix:
           setup:
             image:
-              - windows-2019
+              - windows-2022
             PACKAGING_TASK:
               - default-windows-archive
         agents:
diff --git a/.buildkite/pipelines/pull-request/packaging-tests-windows.yml b/.buildkite/pipelines/pull-request/packaging-tests-windows.yml
index 651a82982460f..df5505bea9a62 100644
--- a/.buildkite/pipelines/pull-request/packaging-tests-windows.yml
+++ b/.buildkite/pipelines/pull-request/packaging-tests-windows.yml
@@ -10,8 +10,6 @@ steps:
         matrix:
           setup:
             image:
-              - windows-2016
-              - windows-2019
               - windows-2022
             PACKAGING_TASK:
               - default-windows-archive
diff --git a/qa/packaging/src/test/java/org/elasticsearch/packaging/test/ArchiveTests.java b/qa/packaging/src/test/java/org/elasticsearch/packaging/test/ArchiveTests.java
index 4e7577be8e5fc..64fbc6176a31c 100644
--- a/qa/packaging/src/test/java/org/elasticsearch/packaging/test/ArchiveTests.java
+++ b/qa/packaging/src/test/java/org/elasticsearch/packaging/test/ArchiveTests.java
@@ -48,7 +48,6 @@
 import static org.junit.Assume.assumeThat;
 import static org.junit.Assume.assumeTrue;
 
-@PackagingTestCase.AwaitsFix(bugUrl = "https://github.com/elastic/elasticsearch/issues/116299")
 public class ArchiveTests extends PackagingTestCase {
 
     @BeforeClass