From 4244c6342509d42576f29dc1dfdfbc437a2f08a9 Mon Sep 17 00:00:00 2001
From: npub1mn7jgtj4w2pd0g0zeuhxsa6jy6p0rewxz4kujt98my82ahfmp72sxjexk7
 <dcfd242e557282d7a1e2cf2e6877522682f1e5c6156dc92ca7d90eaedd3b0f95@sprout-oss.stage.blox.sqprod.co>
Date: Mon, 13 Jul 2026 12:42:37 -0400
Subject: [PATCH] fix(desktop): preserve in-flight draft sync intents

Avoid letting an older asynchronous publish erase a newer edit or leave a concurrent deletion behind it. Rebase any raced tombstone after the accepted draft event.

Co-authored-by: Will Pfleger <pfleger.will@gmail.com>
Signed-off-by: Will Pfleger <pfleger.will@gmail.com>
---
 .../features/messages/lib/draftSync.test.mjs  | 90 +++++++++++++++++++
 .../src/features/messages/lib/draftSync.ts    | 31 ++++++-
 2 files changed, 118 insertions(+), 3 deletions(-)

diff --git a/desktop/src/features/messages/lib/draftSync.test.mjs b/desktop/src/features/messages/lib/draftSync.test.mjs
index ef7508c5d..31e7bd8bf 100644
--- a/desktop/src/features/messages/lib/draftSync.test.mjs
+++ b/desktop/src/features/messages/lib/draftSync.test.mjs
@@ -24,6 +24,7 @@ import {
   clearAllDrafts,
   initDraftStore,
   loadDraftEntry,
+  removeRemoteDraftEntry,
   saveDraftEntry,
 } from "./useDrafts.ts";
 
@@ -379,3 +380,92 @@ test("test_unuploaded_attachment_cancels_stale_text_publish", async () => {
 
   assert.equal(published.length, 0);
 });
+
+function deferred() {
+  let resolve;
+  const promise = new Promise((complete) => {
+    resolve = complete;
+  });
+  return { promise, resolve };
+}
+
+test("test_newer_edit_during_inflight_publish_survives", async () => {
+  setup();
+  const published = [];
+  const firstPublish = deferred();
+  const manager = new DraftSyncManager(pubkey, "wss://relay.example", {
+    deriveAddress: async () => "address-a",
+    encrypt: async (content) => content,
+    fetchEvents: async () => [],
+    sign: async (input) => ({
+      id: `signed-${published.length}`,
+      created_at: input.createdAt ?? 0,
+      kind: input.kind,
+      pubkey,
+      content: input.content,
+      sig: "",
+      tags: input.tags,
+    }),
+    publishEvent: async (event) => {
+      published.push(event);
+      if (published.length === 1) await firstPublish.promise;
+    },
+  });
+
+  manager.queuePublish(channelA, draft(channelA, "older edit"));
+  const flush = manager.flushPublishes();
+  while (published.length === 0) await Promise.resolve();
+  manager.queuePublish(channelA, draft(channelA, "newer edit"));
+  firstPublish.resolve();
+  await flush;
+  await manager.destroy();
+
+  assert.equal(published.length, 2);
+  assert.match(published[1].content, /newer edit/);
+});
+
+test("test_deletion_during_inflight_publish_wins", async () => {
+  setup();
+  const published = [];
+  const firstPublish = deferred();
+  const tombstonePublished = deferred();
+  const manager = new DraftSyncManager(pubkey, "wss://relay.example", {
+    deriveAddress: async () => "address-a",
+    encrypt: async (content) => content,
+    fetchEvents: async () => [],
+    sign: async (input) => ({
+      id: `signed-${published.length}`,
+      created_at: input.createdAt ?? 0,
+      kind: input.kind,
+      pubkey,
+      content: input.content,
+      sig: "",
+      tags: input.tags,
+    }),
+    publishEvent: async (event) => {
+      published.push(event);
+      if (published.length === 1) await firstPublish.promise;
+      if (event.content === "") tombstonePublished.resolve();
+    },
+  });
+
+  const local = draft(channelA, "draft to delete");
+  saveDraftEntry(channelA, local);
+  manager.queuePublish(channelA, local);
+  const flush = manager.flushPublishes();
+  while (published.length === 0) await Promise.resolve();
+  const deletion = manager.queueDeletion(channelA, channelA);
+  await tombstonePublished.promise;
+  removeRemoteDraftEntry(channelA);
+  firstPublish.resolve();
+  await flush;
+  await deletion;
+  await manager.destroy();
+
+  const draftEvent = published.find((event) => event.content !== "");
+  const rebasedTombstone = published.find(
+    (event) => event.content === "" && event.created_at > draftEvent.created_at,
+  );
+  assert.ok(rebasedTombstone);
+  assert.equal(loadDraftEntry(channelA), undefined);
+});
diff --git a/desktop/src/features/messages/lib/draftSync.ts b/desktop/src/features/messages/lib/draftSync.ts
index 3cdf3a3d2..d9863aab9 100644
--- a/desktop/src/features/messages/lib/draftSync.ts
+++ b/desktop/src/features/messages/lib/draftSync.ts
@@ -244,6 +244,10 @@ export class DraftSyncManager {
         limit: 1,
       });
       state = this.state.get(address) ?? state;
+      if (state.pendingDeletion) {
+        this.reschedulePublishes();
+        return;
+      }
       if (state.remoteHead?.content === "") {
         state.pendingPublish = undefined;
         removeRemoteDraftEntry(pending.draftKey);
@@ -271,9 +275,30 @@ export class DraftSyncManager {
         "Timed out publishing draft.",
         "Failed to publish draft.",
       );
-      state.base = event;
-      state.remoteHead = event;
-      state.pendingPublish = undefined;
+      const current = this.state.get(address) ?? state;
+      const deletionWon =
+        current.pendingDeletion !== undefined ||
+        current.remoteHead?.content === "";
+      if (!current.remoteHead || compareHeads(event, current.remoteHead) >= 0) {
+        current.base = event;
+        current.remoteHead = event;
+      }
+      if (current.pendingPublish === pending)
+        current.pendingPublish = undefined;
+      if (deletionWon) {
+        const deletion =
+          current.pendingDeletion ??
+          ({
+            draftKey: pending.draftKey,
+            channelId: pending.channelId,
+            address,
+          } satisfies PendingDeletion);
+        deletion.base = event;
+        current.pendingDeletion = deletion;
+        this.writeSidecar();
+        await this.publishTombstone(deletion);
+      }
+      this.reschedulePublishes();
     } catch (error) {
       console.warn("[draftSync] draft publish failed:", error);
     }