diff --git a/src/main/java/gg/agit/konect/infrastructure/claude/client/ClaudeClient.java b/src/main/java/gg/agit/konect/infrastructure/claude/client/ClaudeClient.java
index 11594abe..ff88f189 100644
--- a/src/main/java/gg/agit/konect/infrastructure/claude/client/ClaudeClient.java
+++ b/src/main/java/gg/agit/konect/infrastructure/claude/client/ClaudeClient.java
@@ -57,8 +57,7 @@ public class ClaudeClient {
 
         ## 응답 규칙
         - 반드시 한국어로 응답
-        - 이모지를 적절히 사용하여 친근하게
-        - 간결하게 2-3문장으로 답변
+        - 답변은 질문한 것에 대해서만 할 것
         - 모르는 테이블이 있으면 먼저 탐색 후 답변
         - 예측/미래 추론 질문은 현재까지의 데이터만 제공하고 예측은 어렵다고 안내
         - 데이터베이스에 정말 없는 정보만 정중히 거절
diff --git a/src/main/java/gg/agit/konect/infrastructure/slack/ai/SlackAIService.java b/src/main/java/gg/agit/konect/infrastructure/slack/ai/SlackAIService.java
index ebce30c8..c984ef59 100644
--- a/src/main/java/gg/agit/konect/infrastructure/slack/ai/SlackAIService.java
+++ b/src/main/java/gg/agit/konect/infrastructure/slack/ai/SlackAIService.java
@@ -24,6 +24,8 @@ public class SlackAIService {
     private static final Pattern MENTION_PATTERN = Pattern.compile("^<@[^>]+>\\s*");
     private static final Pattern MARKDOWN_BOLD_PATTERN =
         Pattern.compile("\\*\\*(.+?)\\*\\*", Pattern.DOTALL);
+    private static final Pattern MARKDOWN_ITALIC_PATTERN =
+        Pattern.compile("(?<!\\*)\\*(?!\\*)([^\\n*]+?)(?<!\\*)\\*(?!\\*)");
     private static final String AI_RESPONSE_PREFIX = ":robot_face: *AI 응답*\n";
     private static final int MAX_HISTORY_MESSAGES = 10;
     private static final String EMPTY_QUERY_MESSAGE =
@@ -175,7 +177,8 @@ private String convertMarkdownToSlack(String text) {
         if (text == null) {
             return null;
         }
-        return MARKDOWN_BOLD_PATTERN.matcher(text).replaceAll("*$1*");
+        String result = MARKDOWN_BOLD_PATTERN.matcher(text).replaceAll("*$1*");
+        return MARKDOWN_ITALIC_PATTERN.matcher(result).replaceAll("*$1*");
     }
 
     private String formatSlackResponse(String response) {