diff --git a/src/bake/DevServer.zig b/src/bake/DevServer.zig
index 895a6e90b5..1e24bbca48 100644
--- a/src/bake/DevServer.zig
+++ b/src/bake/DevServer.zig
@@ -592,6 +592,13 @@ pub fn deinit(dev: *DevServer) void {
                 if (s.underlying) |websocket|
                     websocket.close();
             }
+            // Drain pending libuv close callbacks before freeing memory.
+            // libuv closes handles asynchronously — without this, close
+            // callbacks reference freed socket memory
+            if (bun.Environment.isWindows) {
+                const uv_loop = bun.windows.libuv.Loop.get();
+                _ = bun.windows.libuv.uv_run(uv_loop, .nowait);
+            }
             dev.active_websocket_connections.deinit(alloc);
         },
 
diff --git a/test/js/bun/shell/shell-cmdsub-crash.test.ts b/test/js/bun/shell/shell-cmdsub-crash.test.ts
index 2e07c3201c..a764e724f1 100644
--- a/test/js/bun/shell/shell-cmdsub-crash.test.ts
+++ b/test/js/bun/shell/shell-cmdsub-crash.test.ts
@@ -1,5 +1,5 @@
 import { describe, expect, test } from "bun:test";
-import { bunEnv, bunExe } from "harness";
+import { bunEnv, bunExe, isWindows } from "harness";
 
 // Regression test for use-after-poison in builtin OutputTask callbacks
 // inside command substitution $().
@@ -14,7 +14,7 @@ import { bunEnv, bunExe } from "harness";
 // with many /tmp entries and some permission-denied dirs reliably
 // triggers the ASAN use-after-poison.
 
-describe("builtins in command substitution with errors should not crash", () => {
+describe.skipIf(isWindows)("builtins in command substitution with errors should not crash", () => {
   test("ls /tmp/* in command substitution", async () => {
     await using proc = Bun.spawn({
       cmd: [