diff --git a/packages/runtime-playground/src/preview-server.ts b/packages/runtime-playground/src/preview-server.ts
index 299b29d5..e34982dc 100644
--- a/packages/runtime-playground/src/preview-server.ts
+++ b/packages/runtime-playground/src/preview-server.ts
@@ -136,7 +136,18 @@ function previewProxyServer(target: URL, routes: InternalPreviewRouteRegistry):
       return
     }
 
-    upstreamQueue(() => proxyPreviewRequest(target, incoming, outgoing)).catch((error: Error) => writeProxyError(outgoing, error))
+    upstreamQueue(
+      () => proxyPreviewRequest(target, incoming, outgoing),
+      () => incoming.aborted || incoming.destroyed || outgoing.destroyed,
+      (cancel) => {
+        incoming.once("aborted", cancel)
+        outgoing.once("close", cancel)
+        return () => {
+          incoming.off("aborted", cancel)
+          outgoing.off("close", cancel)
+        }
+      },
+    ).catch((error: Error) => writeProxyError(outgoing, error))
   })
 }
 
@@ -203,6 +214,8 @@ function proxyPreviewRequest(target: URL, incoming: IncomingMessage, outgoing: S
           outgoing.destroy(error)
           settle()
         })
+        response.on("end", settle)
+        response.on("close", settle)
         outgoing.on("finish", settle)
         outgoing.on("close", settle)
         if (bodyTransform) {
@@ -218,6 +231,7 @@ function proxyPreviewRequest(target: URL, incoming: IncomingMessage, outgoing: S
       writeProxyError(outgoing, error)
       settle()
     })
+    incoming.on("aborted", abortUpstream)
     incoming.on("error", () => {
       abortUpstream()
     })
@@ -258,37 +272,80 @@ function previewProxyRequestTarget(incoming: IncomingMessage, target: URL): Prev
   return { upstreamHost: target.host, visibleHost: authority.host, path: rawUrl, port: authority.port || "80", protocol: "http:", rewriteTargetOrigin: true }
 }
 
-function createPreviewProxyQueue(): (task: () => Promise<void>) => Promise<void> {
+function createPreviewProxyQueue(): (
+  task: () => Promise<void>,
+  isCanceled: () => boolean,
+  observeCancellation: (cancel: () => void) => () => void,
+) => Promise<void> {
   let active = false
-  const pending: Array<() => void> = []
-
-  const acquire = async () => {
-    if (!active) {
-      active = true
-      return
-    }
-
-    await new Promise<void>((resolve) => pending.push(resolve))
+  interface PendingRequest {
+    task: () => Promise<void>
+    isCanceled: () => boolean
+    stopObservingCancellation: () => void
+    resolve: () => void
+    reject: (error: unknown) => void
   }
-
-  const release = () => {
-    const next = pending.shift()
-    if (next) {
-      next()
-      return
+  const pending: PendingRequest[] = []
+
+  function release(): void {
+    let next = pending.shift()
+    while (next) {
+      next.stopObservingCancellation()
+      if (!next.isCanceled()) {
+        run(next)
+        return
+      }
+      next.resolve()
+      next = pending.shift()
     }
-
     active = false
   }
 
-  return async (task) => {
-    await acquire()
+  function run(request: PendingRequest): void {
+    request.stopObservingCancellation()
+    if (request.isCanceled()) {
+      request.resolve()
+      release()
+      return
+    }
+    let task: Promise<void>
     try {
-      await task()
-    } finally {
+      task = request.task()
+    } catch (error) {
+      request.reject(error)
       release()
+      return
     }
+    task.then(request.resolve, request.reject).finally(release)
   }
+
+  return (task, isCanceled, observeCancellation) => new Promise<void>((resolve, reject) => {
+    const request: PendingRequest = {
+      task,
+      isCanceled,
+      stopObservingCancellation: () => {},
+      resolve,
+      reject,
+    }
+    const cancel = () => {
+      const index = pending.indexOf(request)
+      if (index === -1) {
+        return
+      }
+      pending.splice(index, 1)
+      request.stopObservingCancellation()
+      resolve()
+    }
+    request.stopObservingCancellation = observeCancellation(cancel)
+
+    if (active) {
+      pending.push(request)
+      return
+    }
+
+    active = true
+    run(request)
+  })
 }
 
 async function listenPreviewProxy(proxy: PreviewProxyServer, port: number, bind: string): Promise<void> {
diff --git a/tests/browser-callback-materialization-contracts.test.ts b/tests/browser-callback-materialization-contracts.test.ts
index 05bb86f3..d5daf8bb 100644
--- a/tests/browser-callback-materialization-contracts.test.ts
+++ b/tests/browser-callback-materialization-contracts.test.ts
@@ -259,6 +259,65 @@ try {
   await closeHttpServer(hangingTargetServer)
 }
 
+let releaseFirstQueuedRequest: (() => void) | undefined
+let firstQueuedRequestReached: (() => void) | undefined
+const firstQueuedRequest = new Promise<void>((resolve) => {
+  firstQueuedRequestReached = resolve
+})
+const queuedTargetRequests: string[] = []
+const queuedTargetServer = createServer((request, response) => {
+  queuedTargetRequests.push(request.url ?? "")
+  if (request.url === "/first") {
+    firstQueuedRequestReached?.()
+    new Promise<void>((resolve) => {
+      releaseFirstQueuedRequest = resolve
+    }).then(() => response.end("first"))
+    return
+  }
+  response.end("third")
+})
+const queuedTargetServerUrl = await listenLocalHttpServer(queuedTargetServer)
+const queuedAbortProxy = await withPreviewProxy({
+  playground: { async run() { return { text: "" } } },
+  serverUrl: queuedTargetServerUrl,
+  async [Symbol.asyncDispose]() {},
+} satisfies PlaygroundCliServer, 0)
+let secondQueuedRequestReached: (() => void) | undefined
+const secondQueuedRequest = new Promise<void>((resolve) => {
+  secondQueuedRequestReached = resolve
+})
+let secondQueuedRequestCanceled: (() => void) | undefined
+const secondQueuedCancellation = new Promise<void>((resolve) => {
+  secondQueuedRequestCanceled = resolve
+})
+const stopObservingQueuedRequest = queuedAbortProxy.previewRoutes?.add((request, response) => {
+  if (request.url === "/second") {
+    secondQueuedRequestReached?.()
+    response.once("close", () => secondQueuedRequestCanceled?.())
+  }
+  return false
+})
+try {
+  const firstRequest = fetch(`${queuedAbortProxy.serverUrl}/first`)
+  await firstQueuedRequest
+
+  const controller = new AbortController()
+  const canceledRequest = fetch(`${queuedAbortProxy.serverUrl}/second`, { signal: controller.signal }).catch((error) => error)
+  await secondQueuedRequest
+  controller.abort()
+  await canceledRequest
+  await secondQueuedCancellation
+
+  releaseFirstQueuedRequest?.()
+  assert.equal(await (await firstRequest).text(), "first")
+  assert.equal(await (await fetch(`${queuedAbortProxy.serverUrl}/third`)).text(), "third")
+  assert.deepEqual(queuedTargetRequests, ["/first", "/third"], "a canceled queued request must not open an upstream request")
+} finally {
+  stopObservingQueuedRequest?.()
+  await queuedAbortProxy[Symbol.asyncDispose]()
+  await closeHttpServer(queuedTargetServer)
+}
+
 const phase = materializationPhaseResult({
   phase: "persist-browser-artifacts",
   status: "completed",