diff --git a/packages/windows-connector/config.sh b/packages/windows-connector/config.sh
index 2b8bbdbf..b2c6d20f 100644
--- a/packages/windows-connector/config.sh
+++ b/packages/windows-connector/config.sh
@@ -1,6 +1,6 @@
 #!/usr/bin/env bash
 #
-# Copyright 2025 Delphix
+# Copyright 2025, 2026 Delphix
 #
 # Licensed under the Apache License, Version 2.0 (the "License");
 # you may not use this file except in compliance with the License.
@@ -24,12 +24,51 @@ function prepare() {
 		openjdk-17-jdk-headless
 }
 
+#
+# Rebuilding windows-connector is expensive, so skip it unless connectorDebVersion
+# (bumped whenever the connector source changes; independent of connectorVersion,
+# which is bumped once per release) has no matching artifact yet. Reuses the same
+# "latest" artifact lookup every package already uses for its build dependencies;
+# fails soft (falls through to a real build) if nothing is found there.
+#
 function build() {
 	CONNECTOR_DIR="${WORKDIR}/repo/appliance/server/connector"
 	INSTALLER_DIR="${WORKDIR}/repo/appliance/host/windows"
+
+	local version
+	version=$(grep "project.ext.connectorDebVersion" "$INSTALLER_DIR/build.gradle" |
+		sed -E "s/.*'([^']+)'.*/\1/")
+	local deb_name="windows-connector_${version}_all.deb"
+
+	# Subshell so a missing "latest" pointer (get_package_dependency_s3_url
+	# calls die/exit) only aborts this lookup, not the whole build.
+	local latest_s3_url
+	latest_s3_url=$(
+		get_package_dependency_s3_url "windows-connector" 1>&2
+		printf '%s' "$_RET"
+	)
+
+	if [[ -n "$latest_s3_url" ]]; then
+		local bucket="${latest_s3_url#s3://}"
+		bucket="${bucket%%/*}"
+		local key="${latest_s3_url#s3://"$bucket"/}"
+
+		if aws s3api head-object --bucket "$bucket" --key "$key/$deb_name" >/dev/null 2>&1; then
+			echo "windows-connector $version already built (latest); nothing to do"
+			#
+			# Marker file, not a special exit code: the Jenkins pipeline checks for
+			# this file's existence to set a NOT_BUILT result instead of relying on
+			# a distinguished exit code from this stage.
+			#
+			touch "$WORKDIR/artifacts/.build_skipped"
+			return 0
+		fi
+	fi
+
+	echo "No reusable artifact found for windows-connector $version; building from source"
 	logmust cd "$CONNECTOR_DIR"
 	logmust sudo ../../gradlew build
 	logmust cd "$INSTALLER_DIR"
 	logmust sudo ../../gradlew createDebPackage
-	logmust sudo mv ./build/distributions/*deb "$WORKDIR/artifacts/"
+	logmust sudo mv ./build/distributions/*.deb "$WORKDIR/artifacts/"
 }