diff --git a/apps/web/src/lib/desktop-sync.ts b/apps/web/src/lib/desktop-sync.ts
index 5471dd1f..b3952317 100644
--- a/apps/web/src/lib/desktop-sync.ts
+++ b/apps/web/src/lib/desktop-sync.ts
@@ -10,6 +10,7 @@ import {
 } from "@edgeever/shared";
 import { api, ApiRequestError } from "@/lib/api";
 import { isDesktopResourceRuntime } from "@/lib/desktop-resources";
+import { notifyMemoIdRemapped, notifyMemoSyncAcknowledged } from "@/lib/sync-events";
 
 type StagedResourceRewrite = { memoId: string; placeholder: string; url: string };
 let lastSyncFailed = false;
@@ -152,12 +153,6 @@ const request = async <M extends keyof DesktopRpcResponses>(method: M, params: D
   return bridge.sidecarRequest<DesktopRpcResponses[M]>(method, params);
 };
 
-const applyRemoteMemo = async (memo: NonNullable<DesktopRpcResponses["memo.get"]>["memo"]) => {
-  await request("sync.apply", {
-    changes: [{ entityType: "memo", operation: "upsert", entityId: memo.id, memo, notebook: null }],
-  });
-};
-
 const applyRemoteNotebook = async (notebook: DesktopRpcResponses["notebook.list"]["notebooks"][number]) => {
   await request("sync.apply", {
     changes: [{ entityType: "notebook", operation: "upsert", entityId: notebook.id, notebook, memo: null }],
@@ -188,9 +183,8 @@ const acknowledge = async (
   remoteNotebook?: DesktopRpcResponses["notebook.list"]["notebooks"][number],
   remoteTemplate?: DesktopRpcResponses["template.list"]["templates"][number],
 ) => {
-  if (remoteMemo) await applyRemoteMemo(remoteMemo);
   if (remoteNotebook) await applyRemoteNotebook(remoteNotebook);
-  await request("sync.outbox.ack", { id: item.id, remoteMemo, remoteNotebook, remoteTemplate });
+  await request("sync.outbox.ack", { id: item.id, version: item.version, remoteMemo, remoteNotebook, remoteTemplate });
 };
 
 const syncOutboxItem = async (item: DesktopOutboxItem, stagedRewrites: StagedResourceRewrite[]) => {
@@ -380,15 +374,21 @@ const syncOutbox = async (stagedRewrites: StagedResourceRewrite[], onlyKinds?: S
       const result = await syncOutboxItem(item, stagedRewrites);
       if (item.kind === "memo.create" && result && typeof result === "object" && "id" in result && typeof result.id === "string") {
         memoIdMappings.set(item.entityId, result.id);
+        // Remap the live editor and advance its cloud base as soon as the
+        // create is acknowledged. Waiting for the workspace-wide sync to end
+        // leaves a window where the next autosave still sends revision 0.
+        notifyMemoIdRemapped(new Map([[item.entityId, result.id]]));
       }
       if (result && typeof result === "object" && "id" in result && typeof result.id === "string" && "contentJson" in result) {
-        syncedMemos.set(result.id, result as DesktopRpcResponses["memo.get"]["memo"]);
+        const syncedMemo = result as DesktopRpcResponses["memo.get"]["memo"];
+        syncedMemos.set(result.id, syncedMemo);
+        notifyMemoSyncAcknowledged(syncedMemo);
       }
       synced += 1;
     } catch (error) {
       const conflict = error instanceof ApiRequestError
         && (error.code === "revision_conflict" || error.code === "content_conflict" || error.code === "edit_session_conflict");
-      await request("sync.outbox.fail", { id: item.id, error: error instanceof Error ? error.message : String(error), conflict });
+      await request("sync.outbox.fail", { id: item.id, version: item.version, error: error instanceof Error ? error.message : String(error), conflict });
       if (conflict) conflicted += 1;
       else failed += 1;
     }
@@ -521,7 +521,9 @@ export const syncDesktopData = () => {
       if (stagedResources.failed === 0 && outbox.failed === 0 && outbox.conflicted === 0 && creates.conflicted === 0) {
         await removeSyncedStagedResources(stagedResources.stagedIds);
       }
-      if (outbox.conflicted === 0 && creates.conflicted === 0 && (typeof navigator === "undefined" || navigator.onLine)) await pullRemoteChanges();
+      const remaining = await request("sync.status", {});
+      if (remaining.pending === 0 && remaining.syncing === 0 && remaining.error === 0 && remaining.conflict === 0
+        && (typeof navigator === "undefined" || navigator.onLine)) await pullRemoteChanges();
       // Catch resources staged while the network sync itself was running.
       await remapStagedResourceMemoIds(creates.memoIdMappings);
       lastSyncFailed = false;
@@ -552,7 +554,7 @@ export const getDesktopSyncSummary = async () => {
 };
 
 export const discardDesktopConflicts = async () => {
-  const response = await request("sync.outbox.list", { limit: 200 });
+  const response = await request("sync.outbox.list", { limit: 200, includeConflicts: true });
   const conflicts = response.items.filter((item) => item.status === "conflict");
   let discarded = 0;
 
@@ -565,7 +567,7 @@ export const discardDesktopConflicts = async () => {
       await request("sync.apply", {
         changes: [{ entityType: "memo", operation: "upsert", entityId: remote.memo.id, memo: remote.memo, notebook: null }],
       });
-      await request("sync.outbox.ack", { id: item.id, remoteMemo: remote.memo });
+      await request("sync.outbox.ack", { id: item.id, version: item.version, remoteMemo: remote.memo });
     } else {
       await request("sync.outbox.discard", { id: item.id });
     }
@@ -585,13 +587,13 @@ export const discardDesktopMemoConflict = async (memoId: string) => {
     changes: [{ entityType: "memo", operation: "upsert", entityId: remote.memo.id, memo: remote.memo, notebook: null }],
   });
 
-  const response = await request("sync.outbox.list", { limit: 200 });
+  const response = await request("sync.outbox.list", { limit: 200, includeConflicts: true });
   for (const item of response.items) {
     if (item.entityId !== memoId || item.status !== "conflict") {
       continue;
     }
     if (item.kind === "memo.update") {
-      await request("sync.outbox.ack", { id: item.id, remoteMemo: remote.memo });
+      await request("sync.outbox.ack", { id: item.id, version: item.version, remoteMemo: remote.memo });
     } else {
       await request("sync.outbox.discard", { id: item.id });
     }
diff --git a/crates/desktop-sidecar/src/database.rs b/crates/desktop-sidecar/src/database.rs
index 2fffefcd..9851c9b4 100644
--- a/crates/desktop-sidecar/src/database.rs
+++ b/crates/desktop-sidecar/src/database.rs
@@ -97,6 +97,43 @@ fn apply_migrations(connection: &Connection, migrations: &Path) -> rusqlite::Res
     Ok(())
 }
 
+fn ensure_sidecar_schema(connection: &Connection) -> rusqlite::Result<()> {
+    connection.execute_batch(
+        "CREATE TABLE IF NOT EXISTS _edgeever_sidecar_meta (
+           key TEXT PRIMARY KEY,
+           value TEXT NOT NULL,
+           updated_at TEXT NOT NULL
+         );
+         CREATE TABLE IF NOT EXISTS _edgeever_sidecar_outbox (
+           id INTEGER PRIMARY KEY AUTOINCREMENT,
+           kind TEXT NOT NULL,
+           entity_id TEXT NOT NULL,
+           payload_json TEXT NOT NULL CHECK (json_valid(payload_json)),
+           status TEXT NOT NULL DEFAULT 'pending',
+           attempt_count INTEGER NOT NULL DEFAULT 0,
+           last_error TEXT,
+           version INTEGER NOT NULL DEFAULT 1,
+           created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+           updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
+         );
+         CREATE INDEX IF NOT EXISTS idx_sidecar_outbox_status ON _edgeever_sidecar_outbox(status, id);",
+    )?;
+
+    let has_version = connection
+        .prepare("PRAGMA table_info(_edgeever_sidecar_outbox)")?
+        .query_map([], |row| row.get::<_, String>(1))?
+        .collect::<Result<Vec<_>, _>>()?
+        .iter()
+        .any(|name| name == "version");
+    if !has_version {
+        connection.execute(
+            "ALTER TABLE _edgeever_sidecar_outbox ADD COLUMN version INTEGER NOT NULL DEFAULT 1",
+            [],
+        )?;
+    }
+    Ok(())
+}
+
 fn copy_directory(source: &Path, destination: &Path) -> io::Result<()> {
     if !source.exists() {
         return Ok(());
@@ -246,6 +283,7 @@ pub(crate) fn restore_database(
     drop(source);
     fs::remove_file(&source_copy).map_err(|error| error.to_string())?;
     apply_migrations(database, migrations).map_err(|error| error.to_string())?;
+    ensure_sidecar_schema(database).map_err(|error| error.to_string())?;
     let resource_source = if resource_restore_source.is_dir() {
         resource_restore_source.as_path()
     } else {
@@ -271,25 +309,7 @@ pub(crate) fn open_database(root: &Path, migrations: &Path) -> rusqlite::Result<
     let existed = root.join("edgeever.sqlite").exists();
     let connection = Connection::open(root.join("edgeever.sqlite"))?;
     connection.pragma_update(None, "journal_mode", "WAL")?;
-    connection.execute_batch(
-        "CREATE TABLE IF NOT EXISTS _edgeever_sidecar_meta (
-           key TEXT PRIMARY KEY,
-           value TEXT NOT NULL,
-           updated_at TEXT NOT NULL
-         );
-         CREATE TABLE IF NOT EXISTS _edgeever_sidecar_outbox (
-           id INTEGER PRIMARY KEY AUTOINCREMENT,
-           kind TEXT NOT NULL,
-           entity_id TEXT NOT NULL,
-           payload_json TEXT NOT NULL CHECK (json_valid(payload_json)),
-           status TEXT NOT NULL DEFAULT 'pending',
-           attempt_count INTEGER NOT NULL DEFAULT 0,
-           last_error TEXT,
-           created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
-           updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now'))
-         );
-         CREATE INDEX IF NOT EXISTS idx_sidecar_outbox_status ON _edgeever_sidecar_outbox(status, id);",
-    )?;
+    ensure_sidecar_schema(&connection)?;
     if existed {
         backup_database(&connection, root)?;
     }
diff --git a/crates/desktop-sidecar/src/main.rs b/crates/desktop-sidecar/src/main.rs
index a8466aa3..f28269bc 100644
--- a/crates/desktop-sidecar/src/main.rs
+++ b/crates/desktop-sidecar/src/main.rs
@@ -33,15 +33,15 @@ fn enqueue_change(
     payload: &Value,
 ) -> Result<(), String> {
     if kind == "memo.update" {
-        let existing: Option<(i64, String)> = database
+        let existing: Option<(i64, String, String)> = database
             .query_row(
-                "SELECT id, payload_json FROM _edgeever_sidecar_outbox WHERE kind = 'memo.update' AND entity_id = ?1 AND status IN ('pending', 'error') ORDER BY id LIMIT 1",
+                "SELECT id, payload_json, status FROM _edgeever_sidecar_outbox WHERE kind = 'memo.update' AND entity_id = ?1 AND status IN ('pending', 'error', 'conflict') ORDER BY id LIMIT 1",
                 [entity_id],
-                |row| Ok((row.get(0)?, row.get(1)?)),
+                |row| Ok((row.get(0)?, row.get(1)?, row.get(2)?)),
             )
             .optional()
             .map_err(|e| e.to_string())?;
-        if let Some((outbox_id, existing_payload)) = existing {
+        if let Some((outbox_id, existing_payload, existing_status)) = existing {
             let previous: Value =
                 serde_json::from_str(&existing_payload).unwrap_or_else(|_| json!({}));
             let mut merged = payload.clone();
@@ -57,10 +57,19 @@ fn enqueue_change(
                     }
                 }
             }
-            database.execute(
-                "UPDATE _edgeever_sidecar_outbox SET payload_json = ?1, status = 'pending', last_error = NULL, updated_at = strftime('%Y-%m-%dT%H:%M:%fZ','now') WHERE id = ?2",
-                rusqlite::params![merged.to_string(), outbox_id],
-            ).map(|_| ()).map_err(|e| e.to_string())?;
+            database
+                .execute(
+                    "UPDATE _edgeever_sidecar_outbox
+                 SET payload_json = ?1,
+                     status = ?2,
+                     last_error = CASE WHEN ?2 = 'conflict' THEN last_error ELSE NULL END,
+                     version = version + 1,
+                     updated_at = strftime('%Y-%m-%dT%H:%M:%fZ','now')
+                 WHERE id = ?3",
+                    rusqlite::params![merged.to_string(), existing_status, outbox_id],
+                )
+                .map(|_| ())
+                .map_err(|e| e.to_string())?;
             return Ok(());
         }
     }
@@ -70,6 +79,43 @@ fn enqueue_change(
     ).map(|_| ()).map_err(|e| e.to_string())
 }
 
+fn memo_remap_base_key(memo_id: &str) -> String {
+    format!("memo.remap-base:{memo_id}")
+}
+
+fn resolve_remapped_memo_base(
+    database: &Connection,
+    memo_id: &str,
+    expected_revision: i64,
+    expected_content_hash: &str,
+) -> (i64, String, bool) {
+    let key = memo_remap_base_key(memo_id);
+    let Some(marker) =
+        meta_value(database, &key).and_then(|value| serde_json::from_str::<Value>(&value).ok())
+    else {
+        return (expected_revision, expected_content_hash.to_owned(), false);
+    };
+    let matches_temporary_base = marker.get("temporaryRevision").and_then(Value::as_i64)
+        == Some(expected_revision)
+        && marker.get("temporaryContentHash").and_then(Value::as_str)
+            == Some(expected_content_hash);
+    if !matches_temporary_base {
+        return (expected_revision, expected_content_hash.to_owned(), false);
+    }
+    (
+        marker
+            .get("remoteRevision")
+            .and_then(Value::as_i64)
+            .unwrap_or(expected_revision),
+        marker
+            .get("remoteContentHash")
+            .and_then(Value::as_str)
+            .unwrap_or(expected_content_hash)
+            .to_owned(),
+        true,
+    )
+}
+
 fn meta_value(database: &Connection, key: &str) -> Option<String> {
     database
         .query_row(
@@ -981,6 +1027,27 @@ fn create_memo(database: &Connection, params: &Value) -> Result<Value, String> {
 fn update_memo(database: &Connection, params: &Value) -> Result<Value, String> {
     let memo_id = string_param(params, "memoId")?;
     let previous = memo_value(database, &memo_id, true)?;
+    let requested_revision = params
+        .get("expectedRevision")
+        .and_then(Value::as_i64)
+        .unwrap_or(0);
+    let requested_content_hash = params
+        .get("expectedContentHash")
+        .and_then(Value::as_str)
+        .unwrap_or("");
+    // A freshly-created desktop note changes from its local id/revision 0 to
+    // the server id/revision while the editor is still live. If an autosave
+    // was already scheduled, translate that one known local base to the exact
+    // create acknowledgement instead of misclassifying our own create as a
+    // remote edit. The marker retains both sides of the mapping, so a genuine
+    // later remote revision still conflicts normally.
+    let (expected_revision, expected_content_hash, consumed_remap_base) =
+        resolve_remapped_memo_base(
+            database,
+            &memo_id,
+            requested_revision,
+            requested_content_hash,
+        );
     let title = params
         .get("title")
         .and_then(Value::as_str)
@@ -1028,12 +1095,20 @@ fn update_memo(database: &Connection, params: &Value) -> Result<Value, String> {
         "memo.update",
         &memo_id,
         &json!({
-            "memoId": memo_id, "expectedRevision": params.get("expectedRevision").and_then(Value::as_i64).unwrap_or(0),
-            "expectedContentHash": params.get("expectedContentHash").and_then(Value::as_str).unwrap_or(""),
+            "memoId": memo_id, "expectedRevision": expected_revision,
+            "expectedContentHash": expected_content_hash,
             "title": params.get("title").and_then(Value::as_str).unwrap_or(""), "contentJson": content_json,
             "contentMarkdown": markdown, "tags": tags
         }),
     )?;
+    if consumed_remap_base {
+        database
+            .execute(
+                "DELETE FROM _edgeever_sidecar_meta WHERE key = ?1",
+                [memo_remap_base_key(&memo_id)],
+            )
+            .map_err(|e| e.to_string())?;
+    }
     memo_value(database, &memo_id, true)
 }
 
@@ -1183,7 +1258,8 @@ fn reset_sync_mirror(database: &Connection) -> Result<(), String> {
          DELETE FROM notebooks
          WHERE id NOT IN (SELECT id FROM _edgeever_bootstrap_preserved_notebooks);
          DELETE FROM _edgeever_sidecar_meta
-         WHERE key IN ('sync.cursor', 'sync.identity', 'sync.last_synced_at');
+         WHERE key IN ('sync.cursor', 'sync.identity', 'sync.last_synced_at')
+            OR key LIKE 'memo.remap-base:%';
          INSERT INTO _edgeever_sidecar_meta (key, value, updated_at)
          VALUES ('sync.bootstrap.reset_pending', '1', strftime('%Y-%m-%dT%H:%M:%fZ','now'))
          ON CONFLICT(key) DO UPDATE SET value = excluded.value, updated_at = excluded.updated_at;",
@@ -1250,12 +1326,16 @@ fn sync_outbox_list(database: &Connection, params: &Value) -> Result<Value, Stri
         .and_then(Value::as_i64)
         .unwrap_or(50)
         .clamp(1, 200);
-    let mut statement = database.prepare(
-        "SELECT id, kind, entity_id, payload_json, attempt_count, status, last_error FROM _edgeever_sidecar_outbox WHERE status IN ('pending', 'error', 'conflict') ORDER BY id LIMIT ?1",
-    ).map_err(|e| e.to_string())?;
+    let include_conflicts = bool_param(params, "includeConflicts", false);
+    let sql = if include_conflicts {
+        "SELECT id, kind, entity_id, payload_json, attempt_count, status, last_error, version FROM _edgeever_sidecar_outbox WHERE status IN ('pending', 'error', 'conflict') ORDER BY id LIMIT ?1"
+    } else {
+        "SELECT id, kind, entity_id, payload_json, attempt_count, status, last_error, version FROM _edgeever_sidecar_outbox WHERE status IN ('pending', 'error') ORDER BY id LIMIT ?1"
+    };
+    let mut statement = database.prepare(sql).map_err(|e| e.to_string())?;
     let rows = statement.query_map([limit], |row| {
         let payload: String = row.get(3)?;
-        Ok(json!({ "id": row.get::<_, i64>(0)?, "kind": row.get::<_, String>(1)?, "entityId": row.get::<_, String>(2)?, "payload": serde_json::from_str::<Value>(&payload).unwrap_or_else(|_| json!({})), "attemptCount": row.get::<_, i64>(4)?, "status": row.get::<_, String>(5)?, "lastError": row.get::<_, Option<String>>(6)? }))
+        Ok(json!({ "id": row.get::<_, i64>(0)?, "kind": row.get::<_, String>(1)?, "entityId": row.get::<_, String>(2)?, "payload": serde_json::from_str::<Value>(&payload).unwrap_or_else(|_| json!({})), "attemptCount": row.get::<_, i64>(4)?, "status": row.get::<_, String>(5)?, "lastError": row.get::<_, Option<String>>(6)?, "version": row.get::<_, i64>(7)? }))
     }).map_err(|e| e.to_string())?;
     let items: Result<Vec<_>, _> = rows.collect();
     Ok(json!({ "items": items.map_err(|e| e.to_string())? }))
@@ -1266,16 +1346,95 @@ fn sync_outbox_ack(database: &Connection, params: &Value) -> Result<Value, Strin
         .get("id")
         .and_then(Value::as_i64)
         .ok_or_else(|| "Missing outbox id".to_owned())?;
-    let (kind, entity_id): (String, String) = database
+    let (kind, entity_id, current_version): (String, String, i64) = database
         .query_row(
-            "SELECT kind, entity_id FROM _edgeever_sidecar_outbox WHERE id = ?1",
+            "SELECT kind, entity_id, version FROM _edgeever_sidecar_outbox WHERE id = ?1",
             [id],
-            |row| Ok((row.get(0)?, row.get(1)?)),
+            |row| Ok((row.get(0)?, row.get(1)?, row.get(2)?)),
         )
         .map_err(|e| e.to_string())?;
+    let requested_version = params.get("version").and_then(Value::as_i64);
+    let superseded = requested_version.is_some_and(|version| version != current_version);
     let remote_memo = params.get("remoteMemo").cloned();
     let remote_notebook = params.get("remoteNotebook").cloned();
     let remote_template = params.get("remoteTemplate").cloned();
+    let temporary_memo_base = if kind == "memo.create" {
+        memo_value(database, &entity_id, true).ok().map(|memo| {
+            (
+                memo.get("revision").and_then(Value::as_i64).unwrap_or(0),
+                memo.get("contentHash")
+                    .and_then(Value::as_str)
+                    .unwrap_or("")
+                    .to_owned(),
+            )
+        })
+    } else {
+        None
+    };
+
+    if kind == "memo.update" && superseded {
+        if let Some(remote) = remote_memo.as_ref() {
+            let remote_revision = remote.get("revision").and_then(Value::as_i64).unwrap_or(0);
+            let remote_hash = remote
+                .get("contentHash")
+                .and_then(Value::as_str)
+                .unwrap_or("");
+            let payload_text: String = database
+                .query_row(
+                    "SELECT payload_json FROM _edgeever_sidecar_outbox WHERE id = ?1",
+                    [id],
+                    |row| row.get(0),
+                )
+                .map_err(|e| e.to_string())?;
+            let mut payload: Value =
+                serde_json::from_str(&payload_text).unwrap_or_else(|_| json!({}));
+            payload["expectedRevision"] = json!(remote_revision);
+            payload["expectedContentHash"] = json!(remote_hash);
+            let tx = database
+                .unchecked_transaction()
+                .map_err(|e| e.to_string())?;
+            // Preserve the successor draft's content while advancing only its
+            // acknowledged cloud base. The next flush will send that draft on
+            // top of the response that just succeeded.
+            tx.execute(
+                "UPDATE memo_contents SET revision = ?1 WHERE memo_id = ?2",
+                rusqlite::params![remote_revision, entity_id],
+            )
+            .map_err(|e| e.to_string())?;
+            tx.execute(
+                "UPDATE _edgeever_sidecar_outbox
+                 SET payload_json = ?1, status = 'pending', last_error = NULL,
+                     updated_at = strftime('%Y-%m-%dT%H:%M:%fZ','now')
+                 WHERE id = ?2",
+                rusqlite::params![payload.to_string(), id],
+            )
+            .map_err(|e| e.to_string())?;
+            tx.commit().map_err(|e| e.to_string())?;
+        }
+        return Ok(json!({
+            "ok": true,
+            "superseded": true,
+            "memo": remote_memo,
+            "notebook": remote_notebook,
+            "template": remote_template
+        }));
+    }
+
+    if let Some(remote) = remote_memo.as_ref() {
+        let remote_id = string_param(remote, "id")?;
+        apply_sync_changes(
+            database,
+            &json!({
+                "changes": [{
+                    "entityType": "memo",
+                    "operation": "upsert",
+                    "entityId": remote_id,
+                    "memo": remote,
+                    "notebook": null
+                }]
+            }),
+        )?;
+    }
     if kind == "memo.create" || kind == "memo.merge" {
         if let Some(remote) = remote_memo.as_ref() {
             let remote_id = string_param(remote, "id")?;
@@ -1287,8 +1446,8 @@ fn sync_outbox_ack(database: &Connection, params: &Value) -> Result<Value, Strin
                 )
                 .map_err(|e| e.to_string())?;
             if remote_exists {
-                // `acknowledge` caches the remote memo before acknowledging the
-                // outbox item, so the remote id normally already exists here.
+                // The acknowledgement caches the remote memo before reconciling
+                // the local placeholder, so the remote id exists here.
                 // A merged local memo can still own resources moved from its
                 // sources. Deleting it directly is rejected by the resources
                 // foreign key and leaves both the local placeholder and remote
@@ -1355,7 +1514,24 @@ fn sync_outbox_ack(database: &Connection, params: &Value) -> Result<Value, Strin
                 } else {
                     outbox_entity
                 };
-                database.execute("UPDATE _edgeever_sidecar_outbox SET entity_id = ?1, payload_json = ?2 WHERE id = ?3", rusqlite::params![next_entity, payload.to_string(), outbox_id]).map_err(|e| e.to_string())?;
+                database.execute("UPDATE _edgeever_sidecar_outbox SET entity_id = ?1, payload_json = ?2, version = version + 1 WHERE id = ?3", rusqlite::params![next_entity, payload.to_string(), outbox_id]).map_err(|e| e.to_string())?;
+            }
+            if kind == "memo.create" {
+                if let Some((temporary_revision, temporary_content_hash)) =
+                    temporary_memo_base.as_ref()
+                {
+                    set_meta(
+                        database,
+                        &memo_remap_base_key(&remote_id),
+                        &json!({
+                            "temporaryRevision": temporary_revision,
+                            "temporaryContentHash": temporary_content_hash,
+                            "remoteRevision": remote.get("revision").and_then(Value::as_i64).unwrap_or(0),
+                            "remoteContentHash": remote.get("contentHash").and_then(Value::as_str).unwrap_or("")
+                        })
+                        .to_string(),
+                    )?;
+                }
             }
         }
     }
@@ -1404,7 +1580,7 @@ fn sync_outbox_ack(database: &Connection, params: &Value) -> Result<Value, Strin
                 } else {
                     outbox_entity
                 };
-                database.execute("UPDATE _edgeever_sidecar_outbox SET entity_id = ?1, payload_json = ?2 WHERE id = ?3", rusqlite::params![next_entity, payload.to_string(), outbox_id]).map_err(|e| e.to_string())?;
+                database.execute("UPDATE _edgeever_sidecar_outbox SET entity_id = ?1, payload_json = ?2, version = version + 1 WHERE id = ?3", rusqlite::params![next_entity, payload.to_string(), outbox_id]).map_err(|e| e.to_string())?;
             }
         }
     }
@@ -1453,15 +1629,24 @@ fn sync_outbox_ack(database: &Connection, params: &Value) -> Result<Value, Strin
                 } else {
                     outbox_entity
                 };
-                database.execute("UPDATE _edgeever_sidecar_outbox SET entity_id = ?1, payload_json = ?2 WHERE id = ?3", rusqlite::params![next_entity, payload.to_string(), outbox_id]).map_err(|e| e.to_string())?;
+                database.execute("UPDATE _edgeever_sidecar_outbox SET entity_id = ?1, payload_json = ?2, version = version + 1 WHERE id = ?3", rusqlite::params![next_entity, payload.to_string(), outbox_id]).map_err(|e| e.to_string())?;
             }
         }
     }
-    database
-        .execute("DELETE FROM _edgeever_sidecar_outbox WHERE id = ?1", [id])
-        .map_err(|e| e.to_string())?;
+    let deleted = if let Some(version) = requested_version {
+        database
+            .execute(
+                "DELETE FROM _edgeever_sidecar_outbox WHERE id = ?1 AND version = ?2",
+                rusqlite::params![id, version],
+            )
+            .map_err(|e| e.to_string())?
+    } else {
+        database
+            .execute("DELETE FROM _edgeever_sidecar_outbox WHERE id = ?1", [id])
+            .map_err(|e| e.to_string())?
+    };
     Ok(
-        json!({ "ok": true, "memo": remote_memo, "notebook": remote_notebook, "template": remote_template }),
+        json!({ "ok": true, "superseded": deleted == 0, "memo": remote_memo, "notebook": remote_notebook, "template": remote_template }),
     )
 }
 
@@ -1479,8 +1664,12 @@ fn sync_outbox_fail(database: &Connection, params: &Value) -> Result<Value, Stri
     } else {
         "error"
     };
-    database.execute("UPDATE _edgeever_sidecar_outbox SET status = ?1, attempt_count = attempt_count + 1, last_error = ?2, updated_at = strftime('%Y-%m-%dT%H:%M:%fZ','now') WHERE id = ?3", rusqlite::params![status, error, id]).map_err(|e| e.to_string())?;
-    Ok(json!({ "ok": true }))
+    let updated = if let Some(version) = params.get("version").and_then(Value::as_i64) {
+        database.execute("UPDATE _edgeever_sidecar_outbox SET status = ?1, attempt_count = attempt_count + 1, last_error = ?2, updated_at = strftime('%Y-%m-%dT%H:%M:%fZ','now') WHERE id = ?3 AND version = ?4", rusqlite::params![status, error, id, version]).map_err(|e| e.to_string())?
+    } else {
+        database.execute("UPDATE _edgeever_sidecar_outbox SET status = ?1, attempt_count = attempt_count + 1, last_error = ?2, updated_at = strftime('%Y-%m-%dT%H:%M:%fZ','now') WHERE id = ?3", rusqlite::params![status, error, id]).map_err(|e| e.to_string())?
+    };
+    Ok(json!({ "ok": true, "superseded": updated == 0 }))
 }
 
 fn sync_outbox_discard(database: &Connection, params: &Value) -> Result<Value, String> {
diff --git a/packages/shared/src/desktop-rpc.ts b/packages/shared/src/desktop-rpc.ts
index 7e6cbbf0..be4b4cb8 100644
--- a/packages/shared/src/desktop-rpc.ts
+++ b/packages/shared/src/desktop-rpc.ts
@@ -153,9 +153,9 @@ export type DesktopRpcParams = {
   "memo.revision.cache": { revision: import("./types").MemoRevision };
   "sync.status": Record<string, never>;
   "sync.bootstrap.prepare": { reset?: boolean };
-  "sync.outbox.list": { limit?: number };
-  "sync.outbox.ack": { id: number; remoteMemo?: MemoDetail; remoteNotebook?: Notebook; remoteTemplate?: MemoTemplate };
-  "sync.outbox.fail": { id: number; error: string; conflict?: boolean };
+  "sync.outbox.list": { limit?: number; includeConflicts?: boolean };
+  "sync.outbox.ack": { id: number; version?: number; remoteMemo?: MemoDetail; remoteNotebook?: Notebook; remoteTemplate?: MemoTemplate };
+  "sync.outbox.fail": { id: number; version?: number; error: string; conflict?: boolean };
   "sync.outbox.discard": { id: number };
   "sync.apply": { changes: Array<{ entityType: "memo" | "notebook"; operation: "upsert" | "delete"; memo?: MemoDetail | null; notebook?: Notebook | null; entityId: string }> };
   "sync.cursor.set": { cursor: number; syncIdentity: string };
@@ -172,6 +172,7 @@ export type DesktopOutboxItem = {
   entityId: string;
   payload: Record<string, unknown>;
   attemptCount: number;
+  version: number;
   status?: "pending" | "syncing" | "conflict" | "error";
   lastError?: string | null;
 };
diff --git a/scripts/test-desktop-sidecar.mjs b/scripts/test-desktop-sidecar.mjs
index 97e54021..2d7557e4 100644
--- a/scripts/test-desktop-sidecar.mjs
+++ b/scripts/test-desktop-sidecar.mjs
@@ -108,6 +108,75 @@ const coalescedUpdates = (await request("sync.outbox.list", { limit: 200 })).ite
 assert.equal(coalescedUpdates.length, 1, "offline autosaves should coalesce into one sidecar outbox item");
 assert.equal(coalescedUpdates[0].payload.contentMarkdown, "latest autosave");
 assert.equal((await request("memo.get", { memoId: coalesced.memo.id })).memo.revision, 0, "local autosaves must not advance the acknowledged cloud revision");
+assert.equal(coalescedUpdates[0].version, 2, "coalescing a newer autosave should advance the outbox version");
+
+const remapRace = await request("memo.create", { notebookId: inbox.id, title: "Remap race", contentMarkdown: "created locally", tags: [] });
+const remapCreate = (await request("sync.outbox.list", { limit: 200 })).items.find((item) => item.kind === "memo.create" && item.entityId === remapRace.memo.id);
+assert.ok(remapCreate, "new desktop memo should have a create outbox item");
+const remoteCreatedMemo = {
+  ...remapRace.memo,
+  id: "memo_remote_remap_race",
+  revision: 1,
+  updatedAt: "2026-08-26T02:15:21.000Z",
+};
+await request("sync.outbox.ack", { id: remapCreate.id, version: remapCreate.version, remoteMemo: remoteCreatedMemo });
+await request("memo.update", {
+  ...updatePayload("first save after create acknowledgement"),
+  memoId: remoteCreatedMemo.id,
+  expectedRevision: 0,
+  expectedContentHash: remapRace.memo.contentHash,
+});
+const remappedUpdate = (await request("sync.outbox.list", { limit: 200 })).items.find((item) => item.kind === "memo.update" && item.entityId === remoteCreatedMemo.id);
+assert.ok(remappedUpdate, "editing immediately after id remapping should queue a remote-id update");
+assert.equal(remappedUpdate.payload.expectedRevision, remoteCreatedMemo.revision, "a scheduled revision-0 autosave should rebase to its own create acknowledgement");
+assert.equal(remappedUpdate.payload.expectedContentHash, remoteCreatedMemo.contentHash);
+
+await request("memo.update", {
+  ...updatePayload("successor typed while the first request was in flight"),
+  memoId: remoteCreatedMemo.id,
+  expectedRevision: remoteCreatedMemo.revision,
+  expectedContentHash: remoteCreatedMemo.contentHash,
+});
+const successorBeforeAck = (await request("sync.outbox.list", { limit: 200 })).items.find((item) => item.id === remappedUpdate.id);
+assert.equal(successorBeforeAck.version, remappedUpdate.version + 1);
+const firstRemoteUpdate = {
+  ...remoteCreatedMemo,
+  revision: 2,
+  contentJson: remappedUpdate.payload.contentJson,
+  contentMarkdown: remappedUpdate.payload.contentMarkdown,
+  contentText: remappedUpdate.payload.contentMarkdown,
+  contentHash: "remote-hash-after-first-save",
+  updatedAt: "2026-08-26T02:15:22.000Z",
+};
+const supersededAck = await request("sync.outbox.ack", {
+  id: remappedUpdate.id,
+  version: remappedUpdate.version,
+  remoteMemo: firstRemoteUpdate,
+});
+assert.equal(supersededAck.superseded, true, "an acknowledgement must not delete a newer coalesced autosave");
+const successorAfterAck = (await request("sync.outbox.list", { limit: 200 })).items.find((item) => item.id === remappedUpdate.id);
+assert.ok(successorAfterAck, "the successor autosave should remain queued");
+assert.equal(successorAfterAck.status, "pending");
+assert.equal(successorAfterAck.payload.contentMarkdown, "successor typed while the first request was in flight");
+assert.equal(successorAfterAck.payload.expectedRevision, firstRemoteUpdate.revision);
+assert.equal(successorAfterAck.payload.expectedContentHash, firstRemoteUpdate.contentHash);
+const preservedSuccessor = await request("memo.get", { memoId: remoteCreatedMemo.id });
+assert.equal(preservedSuccessor.memo.contentMarkdown, "successor typed while the first request was in flight", "acknowledging an older request must preserve the live local draft");
+assert.equal(preservedSuccessor.memo.revision, firstRemoteUpdate.revision, "the preserved successor should advance to the acknowledged cloud revision");
+const secondRemoteUpdate = {
+  ...preservedSuccessor.memo,
+  revision: 3,
+  contentHash: "remote-hash-after-successor",
+  updatedAt: "2026-08-26T02:15:23.000Z",
+};
+const finalAck = await request("sync.outbox.ack", {
+  id: successorAfterAck.id,
+  version: successorAfterAck.version,
+  remoteMemo: secondRemoteUpdate,
+});
+assert.equal(finalAck.superseded, false);
+assert.ok(!(await request("sync.outbox.list", { limit: 200 })).items.some((item) => item.id === successorAfterAck.id), "the exact successor acknowledgement should clear the outbox item");
+assert.equal((await request("memo.get", { memoId: remoteCreatedMemo.id })).memo.revision, secondRemoteUpdate.revision);
 
 const batchNotebook = (await request("notebook.create", { name: "Batch destination" })).notebook;
 const batchFirst = (await request("memo.create", { notebookId: inbox.id, title: "Batch one", contentMarkdown: "batch one", tags: ["batch-tag"] })).memo;
@@ -226,7 +295,8 @@ const conflictMemo = await request("memo.create", { notebookId: inbox.id, title:
 const conflictCandidate = (await request("sync.outbox.list", { limit: 200 })).items.find((item) => item.entityId === conflictMemo.memo.id);
 assert.ok(conflictCandidate, "conflict test should create an outbox item");
 await request("sync.outbox.fail", { id: conflictCandidate.id, error: "test conflict", conflict: true });
-assert.ok((await request("sync.outbox.list", { limit: 200 })).items.some((item) => item.id === conflictCandidate.id && item.status === "conflict"));
+assert.ok(!(await request("sync.outbox.list", { limit: 200 })).items.some((item) => item.id === conflictCandidate.id), "conflicts must not be returned to the automatic retry loop");
+assert.ok((await request("sync.outbox.list", { limit: 200, includeConflicts: true })).items.some((item) => item.id === conflictCandidate.id && item.status === "conflict"), "conflicts should remain available to explicit recovery actions");
 await request("sync.outbox.discard", { id: conflictCandidate.id });
 assert.equal((await request("sync.status")).conflict, 0);