diff --git a/doc/AGENT-ARTIFACTS.md b/doc/AGENT-ARTIFACTS.md
index e380f34c3c5..91edffb52ef 100644
--- a/doc/AGENT-ARTIFACTS.md
+++ b/doc/AGENT-ARTIFACTS.md
@@ -34,6 +34,10 @@ their contents inline does not by itself require a file attachment.
 JSON output intent is recognized from a direct filename or an explicit output
 destination. Ambiguous descriptions of input files joined by `to` remain text
 requests; use `as`, `into`, or an explicit output file when an artifact is required.
+A `Deliverable:` or `Deliverables` label also states the output. A file named
+on that line, or in the list directly below it, is a requested file. This
+includes web page files such as `index.html` and `styles.css`. Items that
+describe a repository change, pull request, commit, or branch do not count.
 
 The completion gate permits a narrow sentence-bound exception for one requested
 file when the following sentence explicitly qualifies it, for example:
diff --git a/server/src/services/native-runtime/native-deliverable-feedback.test.ts b/server/src/services/native-runtime/native-deliverable-feedback.test.ts
index d3637c080bc..3b28bf1e9f6 100644
--- a/server/src/services/native-runtime/native-deliverable-feedback.test.ts
+++ b/server/src/services/native-runtime/native-deliverable-feedback.test.ts
@@ -168,3 +168,40 @@ describe("explicit task-document output", () => {
     expect(explicitlyRequestsTaskDocumentOutput(objective)).toBe(false);
   });
 });
+
+describe("deliverable labels that name files", () => {
+  // The delegated brief from a real first-website run: the worker finished with
+  // index.html and styles.css only in its workspace and the gate did not ask it
+  // to publish them.
+  const delegatedBrief = [
+    "Build a simple, polished static marketing website that introduces the business, Acorn Notes.",
+    "",
+    "Deliverable:",
+    "- A self-contained static website in this task's workspace: index.html plus a stylesheet (for example styles.css). Plain HTML/CSS, no build step.",
+    "- Sections: a hero with the value proposition and a contact call to action.",
+    "",
+    "Constraints:",
+    "- Do not publish or deploy externally; no hosting, DNS, analytics, or third-party services.",
+  ].join("\n");
+  it.each([
+    delegatedBrief,
+    "Deliverables: index.html and styles.css",
+    "## Deliverables\n- `index.html`\n- `styles.css`",
+    "**Deliverable:** report.pdf",
+    "Requested deliverable:\n1. summary.csv with one row per team",
+  ])("requires publication for a labelled file output: %s", objective => {
+    expect(explicitlyRequestsFileOutput(objective)).toBe(true);
+  });
+  it.each([
+    "Build a simple website introducing the business.",
+    "A self-contained static website in this task's workspace: index.html plus a stylesheet.",
+    "Deliverable: a short answer in chat.",
+    "Deliverables:\n- A summary of input.csv in the reply",
+    "Deliverable: a pull request that updates index.html",
+    "Deliverables:\n- Repository change to styles.css",
+    "Deliverable:\n\nindex.html is mentioned after the list ended.",
+    "Deliverable quality matters more than speed for index.html.",
+  ])("does not treat this as a labelled file output: %s", objective => {
+    expect(explicitlyRequestsFileOutput(objective)).toBe(false);
+  });
+});
diff --git a/server/src/services/native-runtime/native-deliverable-feedback.ts b/server/src/services/native-runtime/native-deliverable-feedback.ts
index 3cba6e59d5c..d7d45694b02 100644
--- a/server/src/services/native-runtime/native-deliverable-feedback.ts
+++ b/server/src/services/native-runtime/native-deliverable-feedback.ts
@@ -99,6 +99,36 @@ async function hasCurrentPublicationReceipt(db: Db, companyId: string, receipts:
  * an output requirement or erase a user's request for a file.
  */
 export function explicitlyRequestsFileOutput(objective: string): boolean {
+  return deliverableLabelNamesFile(objective) || explicitlyRequestsFileOutputBySentence(objective);
+}
+
+/** A brief that labels its output ("Deliverable:", "## Deliverables") and names
+ * a file there has stated the requested result as plainly as a creation verb.
+ * Delegated briefs often take this form, so a worker cannot finish with that
+ * file left only in its workspace. Web page files count here: the label makes
+ * them the output, not a repository file being edited in passing.
+ */
+function deliverableLabelNamesFile(objective: string): boolean {
+  const lines = objective.replaceAll("\\_", "_").split(/\r?\n/u);
+  const named = /(?:^|[\s(`'"*:])([^\s/()`'"*:]+\.(?:html?|css|md|txt|json|pdf|docx?|xlsx?|csv|pptx?|png|jpe?g|svg|zip))\b/giu;
+  // A repository change names files it edits; it is delivered as a PR or commit.
+  const namesFile = (text: string) => !/\b(?:[Rr]epo(?:sitory)?|[Pp]ull [Rr]equest|PR|[Cc]ommit|[Bb]ranch)\b/u.test(text) && [...text.matchAll(named)].some(match =>
+    !/\b(?:of|about|from|using|reading|no|without)\s+(?:(?:the|a|an|this|that)\s+)?[`'"*]*$/iu.test(text.slice(0, match.index! + match[0].indexOf(match[1]!))));
+  for (let index = 0; index < lines.length; index += 1) {
+    const label = /^\s*(?:#{1,6}\s*)?(?:\*\*|__)?(?:requested\s+)?deliverables?(?:\*\*|__)?\s*(?::(?:\*\*|__)?\s*(.*)|(?:\*\*|__)?\s*)$/iu.exec(lines[index]!);
+    if (!label) continue;
+    if (namesFile(label[1] ?? "")) return true;
+    // The label's own list: consecutive bullet or numbered items below it.
+    for (let item = index + 1; item < lines.length; item += 1) {
+      const bullet = /^\s*(?:[-*+]|\d+[.)])\s+(.*)$/u.exec(lines[item]!);
+      if (!bullet) break;
+      if (namesFile(bullet[1]!)) return true;
+    }
+  }
+  return false;
+}
+
+function explicitlyRequestsFileOutputBySentence(objective: string): boolean {
   const sentences = objective.replaceAll("\\_", "_").split(/(?:[.!?](?:\s|$)|\n)/iu);
   let precedingFileOutput = false;
   return sentences.some((sentence, index) => {