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 f962d04454..724a0e152f 100644
--- a/server/src/services/native-runtime/native-deliverable-feedback.test.ts
+++ b/server/src/services/native-runtime/native-deliverable-feedback.test.ts
@@ -11,6 +11,7 @@ describe("explicit file output requirements", () => {
     "Do not use external services. Create a file with the results.",
     "Make a file but do not send it to anyone else.",
     "Export a summary of this PDF as CSV.",
+    "Create no temporary files; export the results as CSV.",
   ])("recognizes an explicit output request: %s", objective => {
     expect(explicitlyRequestsFileOutput(objective)).toBe(true);
   });
@@ -26,6 +27,10 @@ describe("explicit file output requirements", () => {
     "Write a summary of this PDF in chat.",
     "Create a review of README.md; reply inline.",
     "Give me advice on file permissions.",
+    "Post exactly one durable progress comment whose entire body is TRACKED, then finish this child task. Create no files and do not delegate or create any further tasks.",
+    "Create no files.",
+    "Generate no attachments and answer in chat.",
+    "Write a reply without any files.",
   ])("does not require a file for a text or source-review request: %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 72b3f8afeb..48aae1ace3 100644
--- a/server/src/services/native-runtime/native-deliverable-feedback.ts
+++ b/server/src/services/native-runtime/native-deliverable-feedback.ts
@@ -71,6 +71,9 @@ export function explicitlyRequestsFileOutput(objective: string): boolean {
     const fileObject = [...output.matchAll(file)].some(match => {
       const prefix = output.slice(0, match.index);
       const suffix = output.slice(match.index + match[0].length);
+      // "Create no files" is a prohibition, even though it contains a creation
+      // verb. Negate this object only; another explicit output can still count.
+      if (/\b(?:no|zero|without(?:\s+any)?)\s+(?:(?:new|temporary|downloadable|attached|additional)\s+)*$/iu.test(prefix)) return false;
       // "Write a summary of this PDF" names input, not a requested file.
       // Explicit export destinations still count after such input references.
       const destination = /\b(?:as|into|to)\s+(?:(?:a|an|the|new|separate|markdown|word|excel)\s+)*$/iu.test(prefix);