diff --git a/backend/src/plugins/Automod/triggers/matchWords.ts b/backend/src/plugins/Automod/triggers/matchWords.ts
index 7967c9de..764eb87c 100644
--- a/backend/src/plugins/Automod/triggers/matchWords.ts
+++ b/backend/src/plugins/Automod/triggers/matchWords.ts
@@ -31,7 +31,6 @@ const configSchema = z.strictObject({
 
 export const MatchWordsTrigger = automodTrigger<MatchResultType>()({
   configSchema,
-
   async match({ pluginData, context, triggerConfig: trigger }) {
     if (!context.message) {
       return;
@@ -39,21 +38,37 @@ export const MatchWordsTrigger = automodTrigger<MatchResultType>()({
 
     if (!regexCache.has(trigger)) {
       const looseMatchingThreshold = Math.min(Math.max(trigger.loose_matching_threshold, 1), 64);
+
       const patterns = trigger.words.map((word) => {
-        let pattern = trigger.loose_matching
-          ? [...word].map((c) => escapeStringRegexp(c)).join(`(?:\\s*|.{0,${looseMatchingThreshold}})`)
-          : escapeStringRegexp(word);
+        let pattern;
+
+        if (trigger.loose_matching) {
+          pattern = [...word]
+            .map((c) => escapeStringRegexp(c))
+            .join(`[\\s\\-_.,!?]{0,${looseMatchingThreshold}}`);
+        } else {
+          pattern = escapeStringRegexp(word);
+        }
 
         if (trigger.only_full_words) {
-          pattern = `\\b${pattern}\\b`;
+          if (trigger.loose_matching) {
+            pattern = `\\b(?:${pattern})\\b`;
+          } else {
+            pattern = `\\b${pattern}\\b`;
+          }
         }
 
         return pattern;
       });
 
-      const mergedRegex = new RegExp(patterns.map((p) => `(?:${p})`).join("|"), trigger.case_sensitive ? "" : "i");
+      const mergedRegex = new RegExp(
+        patterns.map((p) => `(${p})`).join("|"),
+        trigger.case_sensitive ? "" : "i"
+      );
+
       regexCache.set(trigger, [mergedRegex]);
     }
+
     const regexes = regexCache.get(trigger)!;
 
     for await (let [type, str] of matchMultipleTextTypesOnMessage(pluginData, trigger, context.message)) {
@@ -66,11 +81,14 @@ export const MatchWordsTrigger = automodTrigger<MatchResultType>()({
       }
 
       for (const regex of regexes) {
-        if (regex.test(str)) {
+        const match = regex.exec(str);
+        if (match) {
+          const matchedWord = match.slice(1).find(group => group !== undefined) || "";
+
           return {
             extra: {
               type,
-              word: "",
+              word: matchedWord,
             },
           };
         }
@@ -82,6 +100,7 @@ export const MatchWordsTrigger = automodTrigger<MatchResultType>()({
 
   renderMatchInformation({ pluginData, contexts, matchResult }) {
     const partialSummary = getTextMatchPartialSummary(pluginData, matchResult.extra.type, contexts[0]);
-    return `Matched word in ${partialSummary}`;
+    const wordInfo = matchResult.extra.word ? ` (matched: "${matchResult.extra.word}")` : "";
+    return `Matched word in ${partialSummary}${wordInfo}`;
   },
-});
+});
\ No newline at end of file