diff --git a/.azure-pipelines/pipelines.yml b/.azure-pipelines/pipelines.yml
index ffa38e11198d9..ad0ef9b4636f4 100644
--- a/.azure-pipelines/pipelines.yml
+++ b/.azure-pipelines/pipelines.yml
@@ -387,9 +387,13 @@ stages:
           - bash: ci/run_envoy_docker.sh ci/windows_ci_steps.sh
             displayName: "Run Windows CI"
             env:
+              CI_TARGET: "windows"
               ENVOY_DOCKER_BUILD_DIR: "$(Build.StagingDirectory)"
+              SLACK_TOKEN: $(SLACK_TOKEN)
+              REPO_URI: $(Build.Repository.Uri)
+              BUILD_URI: $(Build.BuildUri)
               ENVOY_RBE: "true"
-              BAZEL_BUILD_EXTRA_OPTIONS: "--config=remote-ci --config=remote-msvc-cl --jobs=$(RbeJobs)"
+              BAZEL_BUILD_EXTRA_OPTIONS: "--config=remote-ci --config=remote-msvc-cl --jobs=$(RbeJobs) --flaky_test_attempts=2"
               BAZEL_REMOTE_CACHE: grpcs://remotebuildexecution.googleapis.com
               BAZEL_REMOTE_INSTANCE: projects/envoy-ci/instances/default_instance
               GCP_SERVICE_ACCOUNT_KEY: $(GcpServiceAccountKey)
diff --git a/ci/flaky_test/process_xml.py b/ci/flaky_test/process_xml.py
index 314d55ecce37b..b628f41dcbee5 100755
--- a/ci/flaky_test/process_xml.py
+++ b/ci/flaky_test/process_xml.py
@@ -67,17 +67,18 @@ def processFindOutput(f, problematic_tests):
 # this will likely need adjustments as well.
 def getGitInfo(CI_TARGET):
   ret = ""
-  os.system("git remote -v > ${TMP_OUTPUT_PROCESS_XML}")
-  os.system("git describe --all >> ${TMP_OUTPUT_PROCESS_XML}")
-  os.system("git show >> ${TMP_OUTPUT_PROCESS_XML}")
-  f = open(os.environ['TMP_OUTPUT_PROCESS_XML'], 'r+', encoding='utf-8')
+  os.system('sh -c "git remote -v > ${TMP_OUTPUT_PROCESS_XML}"')
+  os.system('sh -c "git describe --all >> ${TMP_OUTPUT_PROCESS_XML}"')
+  os.system('sh -c "git show >> ${TMP_OUTPUT_PROCESS_XML}"')
   # Fetching the URL from predefined env variable
   envoy_link = os.environ["REPO_URI"]
-  for line in [next(f) for x in range(6)]:
-    if line.split('/')[0] == 'remotes':
-      for token in line.split('/')[1:-1]:
-        envoy_link += '/' + token
-    ret += line
+
+  with open(os.environ['TMP_OUTPUT_PROCESS_XML'], 'r+', encoding='utf-8') as f:
+    for line in [next(f) for x in range(6)]:
+      if line.split('/')[0] == 'remotes':
+        for token in line.split('/')[1:-1]:
+          envoy_link += '/' + token
+      ret += line
 
   ret += "link for additional content: " + envoy_link + " \n"
   ret += "azure build URI: " + os.environ["BUILD_URI"] + " \n"
@@ -100,22 +101,18 @@ def getGitInfo(CI_TARGET):
     sys.exit(0)
   output_msg += getGitInfo(CI_TARGET)
 
+  find_dir = '${TEST_TMPDIR}/**/**/**/**/bazel-testlogs/'
   if CI_TARGET == "MacOS":
-    os.system('find ${TEST_TMPDIR}/ -name "attempt_*.xml" > ${TMP_OUTPUT_PROCESS_XML}')
-  else:
-    os.system(
-        'find ${TEST_TMPDIR}/**/**/**/**/bazel-testlogs/ -name "attempt_*.xml" > ${TMP_OUTPUT_PROCESS_XML}'
-    )
-
-  f = open(os.environ['TMP_OUTPUT_PROCESS_XML'], 'r+')
-  if f.closed:
-    print("cannot open {}".format(os.environ['TMP_OUTPUT_PROCESS_XML']))
+    find_dir = '${TEST_TMPDIR}/'
+  os.system(
+      'sh -c "/usr/bin/find {} -name attempt_*.xml > ${{TMP_OUTPUT_PROCESS_XML}}"'.format(find_dir))
 
   # All output of find command should be either failed or flaky tests, as only then will
   # a test be rerun and have an 'attempt_n.xml' file. problematic_tests holds a lookup
   # table between the last_attempt xml filepath and the failed previous attempt filepath.
   problematic_tests = {}
-  processFindOutput(f, problematic_tests)
+  with open(os.environ['TMP_OUTPUT_PROCESS_XML'], 'r+') as f:
+    processFindOutput(f, problematic_tests)
 
   # Needed to make sure no duplicate flaky tests are going to be reported.
   visited = set()
diff --git a/ci/windows_ci_steps.sh b/ci/windows_ci_steps.sh
index 91e5cf39cfa3f..83775665675fb 100755
--- a/ci/windows_ci_steps.sh
+++ b/ci/windows_ci_steps.sh
@@ -14,6 +14,8 @@ df -h
 # shellcheck source=ci/setup_cache.sh
 . "$(dirname "$0")"/setup_cache.sh
 
+[ -z "${ENVOY_SRCDIR}" ] && export ENVOY_SRCDIR=/c/source
+
 read -ra BAZEL_STARTUP_OPTIONS <<< "${BAZEL_STARTUP_OPTIONS:-}"
 # Default to msvc-cl if not overridden
 read -ra BAZEL_BUILD_EXTRA_OPTIONS <<< "${BAZEL_BUILD_EXTRA_OPTIONS:---config=msvc-cl}"
@@ -75,6 +77,9 @@ tar czf "${ENVOY_BUILD_DIR}"/envoy_binary.tar.gz -C "${ENVOY_DELIVERY_DIR}" envo
 # Test invocations of known-working tests on Windows
 bazel "${BAZEL_STARTUP_OPTIONS[@]}" test "${BAZEL_BUILD_OPTIONS[@]}" //test/... --test_tag_filters=-skip_on_windows,-fails_on_windows,-flaky_on_windows --build_tests_only
 
+echo "running flaky test reporting script"
+"${ENVOY_SRCDIR}"/ci/flaky_test/run_process_xml.sh "$CI_TARGET"
+
 # Build tests that are known-flaky or known-failing to ensure no compilation regressions
 bazel "${BAZEL_STARTUP_OPTIONS[@]}" build "${BAZEL_BUILD_OPTIONS[@]}" //test/... --test_tag_filters=-skip_on_windows,fails_on_windows,flaky_on_windows --build_tests_only