diff --git a/src/lib/backend/convex/user_enabled_models.ts b/src/lib/backend/convex/user_enabled_models.ts
index 764d3ec..a1bc3ce 100644
--- a/src/lib/backend/convex/user_enabled_models.ts
+++ b/src/lib/backend/convex/user_enabled_models.ts
@@ -28,7 +28,7 @@ export const get_enabled = query({
 			.withIndex('by_user', (q) => q.eq('user_id', session.userId))
 			.collect();
 
-		return array.toMap(models, (m) => [getModelKey(m), m]);
+		return array.toRecord(models, (m) => [getModelKey(m), m]);
 	},
 });
 
diff --git a/src/lib/utils/array.ts b/src/lib/utils/array.ts
index 07f315e..1162663 100644
--- a/src/lib/utils/array.ts
+++ b/src/lib/utils/array.ts
@@ -61,6 +61,34 @@ export function sum<T>(arr: T[], fn: (item: T) => number): number {
 	return total;
 }
 
+/** Maps the provided array into a record
+ *
+ * @param arr Array of items to be entered into a record
+ * @param fn A mapping function to transform each item into a key value pair
+ * @returns
+ *
+ * ## Usage
+ * ```ts
+ * const record = toRecord([5, 4, 3, 2, 1], (item, i) => [i, item]);
+ *
+ * console.log(record); // { "0": 5, "1": 4, "2": 3, "3": 2, "4": 1 }
+ * ```
+ */
+export function toRecord<T, V>(
+	arr: T[],
+	fn: (item: T, index: number) => [key: string, value: V]
+): Record<string, V> {
+	const record: Record<string, V> = {};
+
+	for (let i = 0; i < arr.length; i++) {
+		const [key, value] = fn(arr[i]!, i);
+
+		record[key] = value;
+	}
+
+	return record;
+}
+
 /** Maps the provided array into a map
  *
  * @param arr Array of items to be entered into a map
@@ -74,16 +102,16 @@ export function sum<T>(arr: T[], fn: (item: T) => number): number {
  * console.log(map); // Map(5) { 0 => 5, 1 => 4, 2 => 3, 3 => 2, 4 => 1 }
  * ```
  */
-export function toMap<T, V>(
+export function toMap<T, K, V>(
 	arr: T[],
-	fn: (item: T, index: number) => [key: string, value: V]
-): Record<string, V> {
-	const map: Record<string, V> = {};
+	fn: (item: T, index: number) => [key: K, value: V]
+): Map<K, V> {
+	const map: Map<K, V> = new Map();
 
 	for (let i = 0; i < arr.length; i++) {
 		const [key, value] = fn(arr[i]!, i);
 
-		map[key] = value;
+		map.set(key, value);
 	}
 
 	return map;
diff --git a/src/routes/api/generate-message/+server.ts b/src/routes/api/generate-message/+server.ts
index ed08ca8..08e0ecd 100644
--- a/src/routes/api/generate-message/+server.ts
+++ b/src/routes/api/generate-message/+server.ts
@@ -12,6 +12,7 @@ import OpenAI from 'openai';
 import { z } from 'zod/v4';
 import { generationAbortControllers } from './cache.js';
 import { md } from '$lib/utils/markdown-it.js';
+import * as array from '$lib/utils/array';
 
 // Set to true to enable debug logging
 const ENABLE_LOGGING = true;
@@ -371,13 +372,22 @@ async function generateAIResponse({
 		return;
 	}
 
-	const attachedRules = [
-		...rulesResult.value.filter((r) => r.attach === 'always'),
-		...parseMessageForRules(
-			userMessage.content,
+	let attachedRules = rulesResult.value.filter((r) => r.attach === 'always');
+
+	for (const message of messages) {
+		const parsedRules = parseMessageForRules(
+			message.content,
 			rulesResult.value.filter((r) => r.attach === 'manual')
-		),
-	];
+		);
+
+		attachedRules.push(...parsedRules);
+	}
+
+	// remove duplicates
+	attachedRules = array.fromMap(
+		array.toMap(attachedRules, (r) => [r._id, r]),
+		(_k, v) => v
+	);
 
 	log(`Background: ${attachedRules.length} rules attached`, startTime);
 
@@ -412,7 +422,7 @@ async function generateAIResponse({
 					...formattedMessages,
 					{
 						role: 'system' as const,
-						content: `Respond in markdown format. The user may have mentioned one or more rules to follow with the @<rule_name> syntax. Please follow these rules.
+						content: `The user has mentioned one or more rules to follow with the @<rule_name> syntax. Please follow these rules as they apply.
 Rules to follow:
 ${attachedRules.map((r) => `- ${r.name}: ${r.rule}`).join('\n')}`,
 					},