diff --git a/src/commands/ai.ts b/src/commands/ai.ts
index 4431f56..75177e0 100644
--- a/src/commands/ai.ts
+++ b/src/commands/ai.ts
@@ -145,6 +145,12 @@ export function sanitizeForJson(text: string): string {
     .replace(/\t/g, '\\t')
 }
 
+export function escapeMarkdown(text: string): string {
+  if (!text) return '';
+  return text
+    .replace(/([_\*\[\]()~`>#+\-=|{}.!])/g, '\\$1');
+}
+
 export async function preChecks() {
   const envs = [
     "ollamaApi",
@@ -354,16 +360,17 @@ async function handleAiReply(ctx: TextContext, db: NodePgDatabase<typeof schema>
   if (!ctx.chat) return;
   if (aiResponse.success && aiResponse.response) {
     const modelHeader = `🤖 *${model}*  |  🌡️ *${aiTemperature}*\n\n`;
+    const safeResponse = escapeMarkdown(modelHeader + aiResponse.response);
     await rateLimiter.editMessageWithRetry(
       ctx,
       ctx.chat.id,
       replyGenerating.message_id,
-      modelHeader + aiResponse.response,
+      safeResponse,
       { parse_mode: 'Markdown' }
     );
     return;
   }
-  const error = Strings.unexpectedErr.replace("{error}", aiResponse.error);
+  const error = escapeMarkdown(Strings.unexpectedErr.replace("{error}", aiResponse.error));
   await rateLimiter.editMessageWithRetry(
     ctx,
     ctx.chat.id,
diff --git a/src/commands/lastfm.ts b/src/commands/lastfm.ts
index d51ca25..a198772 100644
--- a/src/commands/lastfm.ts
+++ b/src/commands/lastfm.ts
@@ -4,6 +4,7 @@ import axios from 'axios';
 import { getStrings } from '../plugins/checklang';
 import { isOnSpamWatch } from '../spamwatch/spamwatch';
 import spamwatchMiddlewareModule from '../spamwatch/Middleware';
+import { escapeMarkdown } from './ai';
 
 const spamwatchMiddleware = spamwatchMiddlewareModule(isOnSpamWatch);
 
@@ -69,7 +70,7 @@ export default (bot) => {
     const lastUser = ctx.message.text.split(' ')[1];
 
     if (!lastUser) {
-      return ctx.reply(Strings.lastFm.noUser, {
+      return ctx.reply(escapeMarkdown(Strings.lastFm.noUser), {
         parse_mode: "Markdown",
         disable_web_page_preview: true,
         ...(ctx.message?.message_id ? { reply_parameters: { message_id: ctx.message.message_id } } : {})
@@ -79,7 +80,7 @@ export default (bot) => {
     users[userId] = lastUser;
     saveUsers();
 
-    const message = Strings.lastFm.userHasBeenSet.replace('{lastUser}', lastUser);
+    const message = escapeMarkdown(Strings.lastFm.userHasBeenSet.replace('{lastUser}', lastUser));
 
     ctx.reply(message, {
       parse_mode: "Markdown",
@@ -170,9 +171,9 @@ export default (bot) => {
         num_plays = response_plays.data.track.userplaycount;
       } catch (err) {
         console.log(err)
-        const message = Strings.lastFm.apiErr
+        const message = escapeMarkdown(Strings.lastFm.apiErr
           .replace("{lastfmUser}", `[${lastfmUser}](${userUrl})`)
-          .replace("{err}", err);
+          .replace("{err}", err));
         ctx.reply(message, {
           parse_mode: "Markdown",
           disable_web_page_preview: true,
@@ -180,11 +181,11 @@ export default (bot) => {
         });
       };
 
-      let message = Strings.lastFm.listeningTo
+      let message = escapeMarkdown(Strings.lastFm.listeningTo
         .replace("{lastfmUser}", `[${lastfmUser}](${userUrl})`)
         .replace("{nowPlaying}", nowPlaying)
         .replace("{trackName}", `[${trackName}](${trackUrl})`)
-        .replace("{artistName}", `[${artistName}](${artistUrl})`)
+        .replace("{artistName}", `[${artistName}](${artistUrl})`));
 
       if (`${num_plays}` !== "0" && `${num_plays}` !== "1" && `${num_plays}` !== "2" && `${num_plays}` !== "3") {
         message = message
@@ -211,9 +212,9 @@ export default (bot) => {
       };
     } catch (err) {
       const userUrl = `https://www.last.fm/user/${encodeURIComponent(lastfmUser)}`;
-      const message = Strings.lastFm.apiErr
+      const message = escapeMarkdown(Strings.lastFm.apiErr
         .replace("{lastfmUser}", `[${lastfmUser}](${userUrl})`)
-        .replace("{err}", err);
+        .replace("{err}", err));
       ctx.reply(message, {
         parse_mode: "Markdown",
         disable_web_page_preview: true,
diff --git a/src/spamwatch b/src/spamwatch
index cee30dc..5e9de56 160000
--- a/src/spamwatch
+++ b/src/spamwatch
@@ -1 +1 @@
-Subproject commit cee30dc64217e7ec235635f5bf5066eac56eec87
+Subproject commit 5e9de56c7e117811f8dba16fb671b65469688144