diff --git a/apps/web/utils/reply-tracker/outbound.test.ts b/apps/web/utils/reply-tracker/outbound.test.ts
new file mode 100644
index 0000000000..29247d04ee
--- /dev/null
+++ b/apps/web/utils/reply-tracker/outbound.test.ts
@@ -0,0 +1,81 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { handleOutboundReply } from "./outbound";
+import prisma from "@/utils/__mocks__/prisma";
+import { aiDetermineThreadStatus } from "@/utils/ai/reply/determine-thread-status";
+import { applyThreadStatusLabel } from "./label-helpers";
+import { updateThreadTrackers } from "@/utils/reply-tracker/handle-conversation-status";
+import { getEmailAccount, getMockMessage } from "@/__tests__/helpers";
+import { createScopedLogger } from "@/utils/logger";
+import { SystemType } from "@/generated/prisma/enums";
+
+vi.mock("@/utils/prisma");
+vi.mock("@/utils/ai/reply/determine-thread-status");
+vi.mock("./label-helpers");
+vi.mock("@/utils/reply-tracker/handle-conversation-status");
+vi.mock("server-only", () => ({}));
+
+describe("handleOutboundReply", () => {
+  const logger = createScopedLogger("test");
+  const emailAccount = getEmailAccount();
+  const provider = {
+    getThreadMessages: vi.fn(),
+  };
+
+  beforeEach(() => {
+    vi.clearAllMocks();
+  });
+
+  it("should proceed with processing even if the message is not the latest in the thread", async () => {
+    const message = getMockMessage({ id: "sent-msg-1", threadId: "thread1" });
+    const latestMessage = getMockMessage({
+      id: "newer-msg-2",
+      threadId: "thread1",
+    });
+
+    // Mock tracking enabled
+    prisma.rule.findFirst.mockResolvedValue({ id: "rule1" } as any);
+
+    // Mock thread messages - sortByInternalDate sorts asc by default (oldest first)
+    // We mock getThreadMessages to return messages that our internal sortByInternalDate will sort
+    provider.getThreadMessages.mockResolvedValue([message, latestMessage]);
+
+    // Mock AI status
+    vi.mocked(aiDetermineThreadStatus).mockResolvedValue({
+      status: SystemType.AWAITING_REPLY,
+      rationale: "Waiting for response",
+    });
+
+    await handleOutboundReply({
+      emailAccount,
+      message: message as any,
+      provider: provider as any,
+      logger,
+    });
+
+    // Verify it didn't return early
+    expect(aiDetermineThreadStatus).toHaveBeenCalled();
+    expect(applyThreadStatusLabel).toHaveBeenCalledWith(
+      expect.objectContaining({
+        systemType: SystemType.AWAITING_REPLY,
+      }),
+    );
+    expect(updateThreadTrackers).toHaveBeenCalled();
+  });
+
+  it("should return early if outbound tracking is disabled", async () => {
+    const message = getMockMessage({ id: "sent-msg-1", threadId: "thread1" });
+
+    // Mock tracking disabled
+    prisma.rule.findFirst.mockResolvedValue(null);
+
+    await handleOutboundReply({
+      emailAccount,
+      message: message as any,
+      provider: provider as any,
+      logger,
+    });
+
+    expect(provider.getThreadMessages).not.toHaveBeenCalled();
+    expect(aiDetermineThreadStatus).not.toHaveBeenCalled();
+  });
+});
diff --git a/apps/web/utils/reply-tracker/outbound.ts b/apps/web/utils/reply-tracker/outbound.ts
index c9a91717fc..c69c8a0082 100644
--- a/apps/web/utils/reply-tracker/outbound.ts
+++ b/apps/web/utils/reply-tracker/outbound.ts
@@ -46,13 +46,15 @@ export async function handleOutboundReply({
   const { isLatest, sortedMessages } = isMessageLatestInThread(
     message,
     threadMessages,
-    logger,
   );
   if (!isLatest) {
     logger.info(
-      "Skipping outbound check: message is not the latest in the thread",
+      "Outbound message is not the latest in the thread, proceeding anyway.",
+      {
+        processingMessageId: message.id,
+        actualLatestMessageId: sortedMessages.at(-1)?.id,
+      },
     );
-    return; // Stop processing if not the latest
   }
 
   // Prepare thread messages for AI analysis (chronological order, oldest to newest)
@@ -114,22 +116,14 @@ async function isOutboundTrackingEnabled({
 function isMessageLatestInThread(
   message: ParsedMessage,
   threadMessages: ParsedMessage[],
-  logger: Logger,
 ): { isLatest: boolean; sortedMessages: ParsedMessage[] } {
   if (!threadMessages.length) return { isLatest: false, sortedMessages: [] }; // Should not happen if called correctly
 
   const sortedMessages = [...threadMessages].sort(sortByInternalDate());
-  const actualLatestMessage = sortedMessages[sortedMessages.length - 1];
+  const actualLatestMessage = sortedMessages.at(-1);
 
-  if (actualLatestMessage?.id !== message.id) {
-    logger.warn(
-      "Skipping outbound reply check: message is not the latest in the thread",
-      {
-        processingMessageId: message.id,
-        actualLatestMessageId: actualLatestMessage?.id,
-      },
-    );
-    return { isLatest: false, sortedMessages };
-  }
-  return { isLatest: true, sortedMessages };
+  return {
+    isLatest: actualLatestMessage?.id === message.id,
+    sortedMessages,
+  };
 }