From 72b3a0902aeac64ca77a213d1e474f2230cd2d06 Mon Sep 17 00:00:00 2001
From: James Magahern <james@magahern.com>
Date: Tue, 10 Mar 2026 17:40:22 -0700
Subject: [PATCH] Fix de-dup of user messages

---
 server/src/routes.ts | 21 +++++++++++++++++----
 1 file changed, 17 insertions(+), 4 deletions(-)

diff --git a/server/src/routes.ts b/server/src/routes.ts
index 23ac615..6ea9357 100644
--- a/server/src/routes.ts
+++ b/server/src/routes.ts
@@ -16,10 +16,23 @@ type IncomingChatMessage = {
   name?: string;
 };
 
-function sameMessage(a: IncomingChatMessage, b: IncomingChatMessage) {
+function sameMessage(
+  a: { role: string; content: string; name?: string | null },
+  b: { role: string; content: string; name?: string | null }
+) {
   return a.role === b.role && a.content === b.content && (a.name ?? null) === (b.name ?? null);
 }
 
+function isToolCallLogMetadata(value: unknown) {
+  if (!value || typeof value !== "object" || Array.isArray(value)) return false;
+  const record = value as Record<string, unknown>;
+  return record.kind === "tool_call";
+}
+
+function isToolCallLogMessage(message: { role: string; metadata: unknown }) {
+  return message.role === "tool" && isToolCallLogMetadata(message.metadata);
+}
+
 async function storeNonAssistantMessages(chatId: string, messages: IncomingChatMessage[]) {
   const incoming = messages.filter((m) => m.role !== "assistant");
   if (!incoming.length) return;
@@ -27,13 +40,13 @@ async function storeNonAssistantMessages(chatId: string, messages: IncomingChatM
   const existing = await prisma.message.findMany({
     where: { chatId },
     orderBy: { createdAt: "asc" },
-    select: { role: true, content: true, name: true },
+    select: { role: true, content: true, name: true, metadata: true },
   });
-  const existingNonAssistant = existing.filter((m) => m.role !== "assistant");
+  const existingNonAssistant = existing.filter((m) => m.role !== "assistant" && !isToolCallLogMessage(m));
 
   let sharedPrefix = 0;
   const max = Math.min(existingNonAssistant.length, incoming.length);
-  while (sharedPrefix < max && sameMessage(existingNonAssistant[sharedPrefix] as IncomingChatMessage, incoming[sharedPrefix])) {
+  while (sharedPrefix < max && sameMessage(existingNonAssistant[sharedPrefix], incoming[sharedPrefix])) {
     sharedPrefix += 1;
   }