diff --git a/ui/src/pages/chat/chat-outbox-drain.ts b/ui/src/pages/chat/chat-outbox-drain.ts
index 5f0e510fce48..e3975ef91aa0 100644
--- a/ui/src/pages/chat/chat-outbox-drain.ts
+++ b/ui/src/pages/chat/chat-outbox-drain.ts
@@ -305,6 +305,10 @@ async function drainStoredChatOutbox(
       }
       syncVisibleChatQueueProjection(host);
       if (item.localCommandName === "reset") {
+        if ((item.sendAttempts ?? 0) > 0 || item.sendRequestStartedAtMs !== undefined) {
+          setCommandState("unconfirmed", UNCONFIRMED_CHAT_SEND_ERROR);
+          return "blocked";
+        }
         const resetTarget = captureChatCommandTarget(host);
         if (!resetTarget) {
           setCommandState("failed", "The Gateway connection changed. Retry the command.");
@@ -316,25 +320,12 @@ async function drainStoredChatOutbox(
           dependencies.setChatError(host, initialAccess.reason);
           return "blocked";
         }
-        const resetText = item.localCommandArgs ? `/reset ${item.localCommandArgs}` : "/reset";
-        const convertResetToMessage = (sendState?: ChatQueueItem["sendState"]) =>
-          updateQueuedMessageForSession(host, outbox.sessionKey, item.id, (entry) => ({
-            ...entry,
-            localCommandArgs: undefined,
-            localCommandName: undefined,
-            refreshSessions: true,
-            text: resetText,
-            ...(sendState ? { sendState } : {}),
-          }));
         const confirmation = await confirmConversationResetForCurrentSession(host, {
           sessionKey: outbox.sessionKey,
           ...(outbox.agentId ? { agentId: outbox.agentId } : {}),
         });
         if (confirmation === "deferred") {
-          const approvedDuringRun =
-            visibleSessionMatches(host, outbox.sessionKey, outbox.agentId) && host.chatRunId;
-          const deferCommand = approvedDuringRun ? convertResetToMessage : setCommandState;
-          deferCommand("waiting-idle");
+          setCommandState("waiting-idle");
           return "blocked";
         }
         if (confirmation === "cancelled") {
@@ -353,7 +344,15 @@ async function drainStoredChatOutbox(
           ...lane.pendingOptions.get(item.id),
           target: resetTarget,
         });
-        if (!convertResetToMessage()) {
+        const result = await dependencies.sendQueuedChatMessage(
+          host,
+          item.id,
+          lane.pendingOptions.get(item.id),
+          outbox.sessionKey,
+        );
+        lane.outcomes.set(item.id, result);
+        lane.pendingOptions.delete(item.id);
+        if (result !== "sent") {
           return "blocked";
         }
         continue;
diff --git a/ui/src/pages/chat/chat-send-delivery.ts b/ui/src/pages/chat/chat-send-delivery.ts
index b0a3eaf9fbc6..ddad471d9dc8 100644
--- a/ui/src/pages/chat/chat-send-delivery.ts
+++ b/ui/src/pages/chat/chat-send-delivery.ts
@@ -186,7 +186,8 @@ async function sendQueuedChatMessage(
 ): Promise<QueuedChatSendResult> {
   const storageMode = options?.storageMode ?? "durable";
   const queued = readQueuedMessageById(host, id);
-  if (!queued || queued.pendingRunId || queued.localCommandName) {
+  const approvedReset = queued?.localCommandName === "reset" && Boolean(options?.target);
+  if (!queued || queued.pendingRunId || (queued.localCommandName && !approvedReset)) {
     return "failed";
   }
   const queueSessionKey = queued.sessionKey ?? queuedSessionKey;
@@ -248,6 +249,13 @@ async function sendQueuedChatMessage(
     setChatError(host, OFFLINE_QUEUE_STORAGE_ERROR);
     return prepared;
   }
+  if (approvedReset) {
+    prepared = {
+      ...prepared,
+      refreshSessions: true,
+      text: prepared.localCommandArgs ? `/reset ${prepared.localCommandArgs}` : "/reset",
+    };
+  }
   const message = prepared.text.trim();
   const attachments = prepared.attachments ?? [];
   if (!message && attachments.length === 0) {
@@ -717,6 +725,7 @@ async function sendResetSlashCommand(
     previousDraft: options.previousDraft,
     restoreDraft: options.restoreDraft,
     routingSessionKey: host.sessionKey,
+    target: options.target,
   });
 }
 
diff --git a/ui/src/pages/chat/chat-send.test.ts b/ui/src/pages/chat/chat-send.test.ts
index 99f460ecdce0..6c24d4ca2f27 100644
--- a/ui/src/pages/chat/chat-send.test.ts
+++ b/ui/src/pages/chat/chat-send.test.ts
@@ -4317,16 +4317,16 @@ describe("handleSendChat", () => {
     expect(approvedReset).toEqual(
       expect.objectContaining({
         id: item.id,
+        localCommandName: "reset",
         sendState: "waiting-idle",
         text: "/reset",
       }),
     );
-    expect(approvedReset).not.toHaveProperty("localCommandName");
 
     host.chatRunId = null;
     await retryReconnectableQueuedChatSends(host);
 
-    expect(confirmConversationReset).toHaveBeenCalledOnce();
+    expect(confirmConversationReset).toHaveBeenCalledTimes(2);
     expect(sendPayloads.map((payload) => payload.message)).toEqual(["/reset"]);
     expect(listStoredChatOutboxes(host)).toStrictEqual([]);
   });