diff --git a/src/features/joel/responder.ts b/src/features/joel/responder.ts
index 31cad94..fa0e35c 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, messageRepository } from "../../database";
+import { db } from "../../database";
 import { personalities, botOptions } from "../../database/schema";
 import { eq } from "drizzle-orm";
 import { buildStyledPrompt, STYLE_MODIFIERS } from "./personalities";
@@ -22,6 +22,11 @@ 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;
+const CONVERSATION_CONTEXT_SCAN_LIMIT = Math.max(20, CONVERSATION_CONTEXT_MAX_MESSAGES * 5);
+const CONVERSATION_CONTEXT_MAX_LINKS_PER_MESSAGE = 2;
+const CONVERSATION_CONTEXT_MAX_MEDIA_MESSAGES = 2;
+const CONVERSATION_CONTEXT_MAX_MEDIA_ATTACHMENTS = 3;
+const URL_REGEX = /https?:\/\/[^\s<>()]+/gi;
 
 type ResponseTrigger = "free-will" | "summoned" | "classifier" | "none";
 
@@ -377,50 +382,133 @@ The image URL will appear in your response for the user to see.`;
    */
   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,
-        }
-      );
+      const fetched = await message.channel.messages.fetch({
+        limit: CONVERSATION_CONTEXT_SCAN_LIMIT,
+      });
+
+      const cutoffTimestamp = Date.now() - CONVERSATION_CONTEXT_WINDOW_MINUTES * 60 * 1000;
+      const recent = Array.from(fetched.values())
+        .filter((recentMessage) => recentMessage.id !== message.id)
+        .filter((recentMessage) => recentMessage.createdTimestamp >= cutoffTimestamp)
+        .sort((a, b) => a.createdTimestamp - b.createdTimestamp)
+        .slice(-CONVERSATION_CONTEXT_MAX_MESSAGES);
 
       if (recent.length === 0) {
         return null;
       }
 
       const contextLines = recent
-        .map(({ message: recentMessage, userName }) => {
-          const author = userName || recentMessage.user_id || "Unknown";
-          const content = (recentMessage.content || "")
+        .map((recentMessage) => {
+          const author = recentMessage.member?.displayName || recentMessage.author.username || "Unknown";
+          const content = (recentMessage.cleanContent || "")
             .replace(/\s+/g, " ")
             .trim()
             .slice(0, 220);
 
+          const links = this.extractLinks(recentMessage.content);
+          const linkPreview = links.slice(0, CONVERSATION_CONTEXT_MAX_LINKS_PER_MESSAGE).join(", ");
+          const linksSuffix = links.length > 0
+            ? ` [links: ${linkPreview}${links.length > CONVERSATION_CONTEXT_MAX_LINKS_PER_MESSAGE ? ", ..." : ""}]`
+            : "";
+
+          if (!content && links.length > 0) {
+            return `- ${author}: [shared links] ${linkPreview}${links.length > CONVERSATION_CONTEXT_MAX_LINKS_PER_MESSAGE ? ", ..." : ""}`;
+          }
+
+          if (!content && recentMessage.attachments.size > 0) {
+            const attachmentWord = recentMessage.attachments.size === 1 ? "attachment" : "attachments";
+            return `- ${author}: [shared ${recentMessage.attachments.size} ${attachmentWord}]`;
+          }
+
           if (!content) {
             return null;
           }
 
-          return `- ${author}: ${content}`;
+          return `- ${author}: ${content}${linksSuffix}`;
         })
         .filter((line): line is string => Boolean(line));
 
-      if (contextLines.length === 0) {
+      const mediaContext = await this.buildRecentMediaContext(recent);
+
+      if (contextLines.length === 0 && !mediaContext) {
         return null;
       }
 
-      return [
+      const sections = [
         `Recent channel context (last ${CONVERSATION_CONTEXT_MAX_MESSAGES} messages within ${CONVERSATION_CONTEXT_WINDOW_MINUTES} minutes):`,
         ...contextLines,
-      ].join("\n");
+      ];
+
+      if (mediaContext) {
+        sections.push("", mediaContext);
+      }
+
+      return sections.join("\n");
     } catch (error) {
       logger.error("Failed to build conversation context", error);
       return null;
     }
   },
 
+  extractLinks(content: string): string[] {
+    const matches = content.match(URL_REGEX) ?? [];
+    const cleaned = matches.map((url) => url.replace(/[),.!?]+$/, ""));
+    return Array.from(new Set(cleaned));
+  },
+
+  async buildRecentMediaContext(recentMessages: Message[]): Promise<string | null> {
+    const mediaMessages = recentMessages
+      .filter((recentMessage) => recentMessage.attachments.size > 0)
+      .slice(-CONVERSATION_CONTEXT_MAX_MEDIA_MESSAGES);
+
+    if (mediaMessages.length === 0) {
+      return null;
+    }
+
+    const vision = getVisionService();
+    const mediaLines: string[] = [];
+    let remainingAttachments = CONVERSATION_CONTEXT_MAX_MEDIA_ATTACHMENTS;
+
+    for (const mediaMessage of mediaMessages) {
+      if (remainingAttachments <= 0) {
+        break;
+      }
+
+      const attachments: Attachment[] = mediaMessage.attachments
+        .map((att) => ({
+          url: att.url,
+          name: att.name,
+          contentType: att.contentType,
+          size: att.size,
+        }))
+        .slice(0, remainingAttachments);
+
+      if (attachments.length === 0) {
+        continue;
+      }
+
+      const analyses = await vision.analyzeAttachments(attachments, mediaMessage.cleanContent);
+      if (analyses.length === 0) {
+        continue;
+      }
+
+      remainingAttachments -= analyses.length;
+
+      const author = mediaMessage.member?.displayName || mediaMessage.author.username || "Unknown";
+      const attachmentSummaries = analyses
+        .map((analysis) => `${analysis.attachmentName}: ${analysis.description}`)
+        .join(" | ");
+
+      mediaLines.push(`- ${author}: ${attachmentSummaries}`);
+    }
+
+    if (mediaLines.length === 0) {
+      return null;
+    }
+
+    return ["Recent shared media:", ...mediaLines].join("\n");
+  },
+
   /**
    * Extract and analyze attachments from a message using vision AI
    */