diff --git a/.bazelversion b/.bazelversion
index ee74734aa225..fae6e3d04b2c 100644
--- a/.bazelversion
+++ b/.bazelversion
@@ -1 +1 @@
-4.1.0
+4.2.1
diff --git a/bazel/envoy_binary.bzl b/bazel/envoy_binary.bzl
index 6ea24b9888cf..d7a17c2ff615 100644
--- a/bazel/envoy_binary.bzl
+++ b/bazel/envoy_binary.bzl
@@ -22,7 +22,8 @@ def envoy_cc_binary(
         stamped = False,
         deps = [],
         linkopts = [],
-        tags = []):
+        tags = [],
+        features = []):
     if not linkopts:
         linkopts = _envoy_linkopts()
     if stamped:
@@ -42,6 +43,7 @@ def envoy_cc_binary(
         stamp = 1,
         deps = deps,
         tags = tags,
+        features = features,
     )
 
 # Select the given values if exporting is enabled in the current build.
diff --git a/ci/windows_ci_steps.sh b/ci/windows_ci_steps.sh
index eed32c121886..110535e63576 100755
--- a/ci/windows_ci_steps.sh
+++ b/ci/windows_ci_steps.sh
@@ -91,11 +91,13 @@ fi
 if [[ $BUILD_ENVOY_STATIC -eq 1 ]]; then
   bazel "${BAZEL_STARTUP_OPTIONS[@]}" build "${BAZEL_BUILD_OPTIONS[@]}" //source/exe:envoy-static
 
-  # Copy binary to delivery directory
+  # Copy binary and pdb to delivery directory
   cp -f bazel-bin/source/exe/envoy-static.exe "${ENVOY_DELIVERY_DIR}/envoy.exe"
+  cp -f bazel-bin/source/exe/envoy-static.pdb "${ENVOY_DELIVERY_DIR}/envoy.pdb"
 
   # Copy for azp, creating a tar archive
   tar czf "${ENVOY_BUILD_DIR}"/envoy_binary.tar.gz -C "${ENVOY_DELIVERY_DIR}" envoy.exe
+  tar czf "${ENVOY_BUILD_DIR}"/envoy_binary_debug.tar.gz -C "${ENVOY_DELIVERY_DIR}" envoy.exe envoy.pdb
 fi
 
 # Test invocations of known-working tests on Windows
diff --git a/source/exe/BUILD b/source/exe/BUILD
index f3fb551eb83a..0eb4078c164c 100644
--- a/source/exe/BUILD
+++ b/source/exe/BUILD
@@ -22,6 +22,10 @@ alias(
 
 envoy_cc_binary(
     name = "envoy-static",
+    features = select({
+        "//bazel:windows_opt_build": ["generate_pdb_file"],
+        "//conditions:default": [],
+    }),
     stamped = True,
     deps = [":envoy_main_entry_lib"],
 )