diff --git a/src/database/repositories/message.repository.ts b/src/database/repositories/message.repository.ts
index 7f6d0ea..fe78ae5 100644
--- a/src/database/repositories/message.repository.ts
+++ b/src/database/repositories/message.repository.ts
@@ -2,7 +2,7 @@
  * Message repository - handles all message-related database operations
  */
 
-import { and, eq } from "drizzle-orm";
+import { and, desc, eq } from "drizzle-orm";
 import { db } from "../connection";
 import { messages, users, type InsertMessage, type Message } from "../schema";
 
@@ -28,4 +28,57 @@ export const messageRepository = {
       userName: r.users?.name ?? null,
     }));
   },
+
+  async findRecentContext(
+    guildId: string,
+    channelId: string,
+    options?: {
+      maxMessages?: number;
+      withinMinutes?: number;
+      excludeMessageId?: string;
+    }
+  ): Promise<Array<{ message: Message; userName: string | null }>> {
+    const maxMessages = options?.maxMessages ?? 5;
+    const withinMinutes = options?.withinMinutes ?? 20;
+    const scanLimit = Math.max(20, maxMessages * 5);
+
+    const results = await db
+      .select()
+      .from(messages)
+      .where(
+        and(eq(messages.guild_id, guildId), eq(messages.channel_id, channelId))
+      )
+      .leftJoin(users, eq(users.id, messages.user_id))
+      .orderBy(desc(messages.timestamp))
+      .limit(scanLimit);
+
+    const now = Date.now();
+    const cutoff = now - withinMinutes * 60 * 1000;
+
+    const filtered = results
+      .filter((r) => {
+        if (options?.excludeMessageId && r.messages.id === options.excludeMessageId) {
+          return false;
+        }
+
+        const timestamp = r.messages.timestamp;
+        if (!timestamp) {
+          return true;
+        }
+
+        const parsedTs = Date.parse(timestamp);
+        if (Number.isNaN(parsedTs)) {
+          return true;
+        }
+
+        return parsedTs >= cutoff;
+      })
+      .slice(0, maxMessages)
+      .reverse();
+
+    return filtered.map((r) => ({
+      message: r.messages,
+      userName: r.users?.name ?? null,
+    }));
+  },
 };
diff --git a/src/features/joel/responder.ts b/src/features/joel/responder.ts
index 6805a3f..31cad94 100644
--- a/src/features/joel/responder.ts
+++ b/src/features/joel/responder.ts
@@ -7,7 +7,7 @@ import type { BotClient } from "../../core/client";
 import { config } from "../../core/config";
 import { createLogger } from "../../core/logger";
 import { getAiService, getVisionService, type MessageStyle, type ToolContext, type Attachment } from "../../services/ai";
-import { db } from "../../database";
+import { db, messageRepository } from "../../database";
 import { personalities, botOptions } from "../../database/schema";
 import { eq } from "drizzle-orm";
 import { buildStyledPrompt, STYLE_MODIFIERS } from "./personalities";
@@ -20,6 +20,8 @@ const logger = createLogger("Features:Joel");
 const DIRECTED_CLASSIFICATION_LIMIT_PER_HOUR = 20;
 const DIRECTED_CLASSIFICATION_WINDOW_MS = 60 * 60 * 1000;
 const directedClassificationBudget = new Map<string, { windowStart: number; count: number }>();
+const CONVERSATION_CONTEXT_MAX_MESSAGES = 5;
+const CONVERSATION_CONTEXT_WINDOW_MINUTES = 20;
 
 type ResponseTrigger = "free-will" | "summoned" | "classifier" | "none";
 
@@ -348,6 +350,12 @@ The image URL will appear in your response for the user to see.`;
       }
     }
 
+    // Add recent conversation context so Joel can follow ongoing chat
+    const conversationContext = await this.buildConversationContext(message);
+    if (conversationContext) {
+      prompt = `${conversationContext}\n\nCurrent message:\n${prompt}`;
+    }
+
     // Analyze attachments if present (images, etc.)
     const attachmentDescriptions = await this.analyzeAttachments(message);
     if (attachmentDescriptions) {
@@ -364,6 +372,55 @@ The image URL will appear in your response for the user to see.`;
     return response.text || null;
   },
 
+  /**
+   * Build a compact conversation context from recent messages in this channel.
+   */
+  async buildConversationContext(message: Message<true>): Promise<string | null> {
+    try {
+      const recent = await messageRepository.findRecentContext(
+        message.guildId,
+        message.channelId,
+        {
+          maxMessages: CONVERSATION_CONTEXT_MAX_MESSAGES,
+          withinMinutes: CONVERSATION_CONTEXT_WINDOW_MINUTES,
+          excludeMessageId: message.id,
+        }
+      );
+
+      if (recent.length === 0) {
+        return null;
+      }
+
+      const contextLines = recent
+        .map(({ message: recentMessage, userName }) => {
+          const author = userName || recentMessage.user_id || "Unknown";
+          const content = (recentMessage.content || "")
+            .replace(/\s+/g, " ")
+            .trim()
+            .slice(0, 220);
+
+          if (!content) {
+            return null;
+          }
+
+          return `- ${author}: ${content}`;
+        })
+        .filter((line): line is string => Boolean(line));
+
+      if (contextLines.length === 0) {
+        return null;
+      }
+
+      return [
+        `Recent channel context (last ${CONVERSATION_CONTEXT_MAX_MESSAGES} messages within ${CONVERSATION_CONTEXT_WINDOW_MINUTES} minutes):`,
+        ...contextLines,
+      ].join("\n");
+    } catch (error) {
+      logger.error("Failed to build conversation context", error);
+      return null;
+    }
+  },
+
   /**
    * Extract and analyze attachments from a message using vision AI
    */