diff --git a/extensions/tlon/src/channel.ts b/extensions/tlon/src/channel.ts
index 4d56cfd93..1be1bb9db 100644
--- a/extensions/tlon/src/channel.ts
+++ b/extensions/tlon/src/channel.ts
@@ -13,7 +13,7 @@ import {
 import { resolveTlonAccount, listTlonAccountIds } from "./types.js";
 import { formatTargetHint, normalizeShip, parseTlonTarget } from "./targets.js";
 import { ensureUrbitConnectPatched, Urbit } from "./urbit/http-api.js";
-import { buildMediaText, sendDm, sendGroupMessage } from "./urbit/send.js";
+import { buildMediaText, buildMediaStory, sendDm, sendGroupMessage, sendDmWithStory, sendGroupMessageWithStory } from "./urbit/send.js";
 import { monitorTlonProvider } from "./monitor/index.js";
 import { tlonChannelConfigSchema } from "./config-schema.js";
 import { tlonOnboardingAdapter } from "./onboarding.js";
@@ -154,15 +154,50 @@ const tlonOutbound: ChannelOutboundAdapter = {
     }
   },
   sendMedia: async ({ cfg, to, text, mediaUrl, accountId, replyToId, threadId }) => {
-    const mergedText = buildMediaText(text, mediaUrl);
-    return await tlonOutbound.sendText({
-      cfg,
-      to,
-      text: mergedText,
-      accountId,
-      replyToId,
-      threadId,
+    const account = resolveTlonAccount(cfg as ClawdbotConfig, accountId ?? undefined);
+    if (!account.configured || !account.ship || !account.url || !account.code) {
+      throw new Error("Tlon account not configured");
+    }
+
+    const parsed = parseTlonTarget(to);
+    if (!parsed) {
+      throw new Error(`Invalid Tlon target. Use ${formatTargetHint()}`);
+    }
+
+    const api = await createHttpPokeApi({
+      url: account.url,
+      ship: account.ship,
+      code: account.code,
     });
+
+    try {
+      const fromShip = normalizeShip(account.ship);
+      const story = buildMediaStory(text, mediaUrl);
+      
+      if (parsed.kind === "dm") {
+        return await sendDmWithStory({
+          api,
+          fromShip,
+          toShip: parsed.ship,
+          story,
+        });
+      }
+      const replyId = (replyToId ?? threadId) ? String(replyToId ?? threadId) : undefined;
+      return await sendGroupMessageWithStory({
+        api,
+        fromShip,
+        hostShip: parsed.hostShip,
+        channelName: parsed.channelName,
+        story,
+        replyToId: replyId,
+      });
+    } finally {
+      try {
+        await api.delete();
+      } catch {
+        // ignore cleanup errors
+      }
+    }
   },
 };
 
diff --git a/extensions/tlon/src/urbit/send.ts b/extensions/tlon/src/urbit/send.ts
index 658b87e3f..23b8203f1 100644
--- a/extensions/tlon/src/urbit/send.ts
+++ b/extensions/tlon/src/urbit/send.ts
@@ -1,5 +1,5 @@
 import { scot, da } from "@urbit/aura";
-import { markdownToStory, type Story } from "./story.js";
+import { markdownToStory, createImageBlock, isImageUrl, type Story } from "./story.js";
 
 export type TlonPokeApi = {
   poke: (params: { app: string; mark: string; json: unknown }) => Promise<unknown>;
@@ -12,8 +12,19 @@ type SendTextParams = {
   text: string;
 };
 
+type SendStoryParams = {
+  api: TlonPokeApi;
+  fromShip: string;
+  toShip: string;
+  story: Story;
+};
+
 export async function sendDm({ api, fromShip, toShip, text }: SendTextParams) {
   const story: Story = markdownToStory(text);
+  return sendDmWithStory({ api, fromShip, toShip, story });
+}
+
+export async function sendDmWithStory({ api, fromShip, toShip, story }: SendStoryParams) {
   const sentAt = Date.now();
   const idUd = scot('ud', da.fromUnix(sentAt));
   const id = `${fromShip}/${idUd}`;
@@ -53,6 +64,15 @@ type SendGroupParams = {
   replyToId?: string | null;
 };
 
+type SendGroupStoryParams = {
+  api: TlonPokeApi;
+  fromShip: string;
+  hostShip: string;
+  channelName: string;
+  story: Story;
+  replyToId?: string | null;
+};
+
 export async function sendGroupMessage({
   api,
   fromShip,
@@ -62,6 +82,17 @@ export async function sendGroupMessage({
   replyToId,
 }: SendGroupParams) {
   const story: Story = markdownToStory(text);
+  return sendGroupMessageWithStory({ api, fromShip, hostShip, channelName, story, replyToId });
+}
+
+export async function sendGroupMessageWithStory({
+  api,
+  fromShip,
+  hostShip,
+  channelName,
+  story,
+  replyToId,
+}: SendGroupStoryParams) {
   const sentAt = Date.now();
 
   // Format reply ID as @ud (with dots) - required for Tlon to recognize thread replies
@@ -127,3 +158,27 @@ export function buildMediaText(text: string | undefined, mediaUrl: string | unde
   if (cleanUrl) return cleanUrl;
   return cleanText;
 }
+
+/**
+ * Build a story with text and optional media (image)
+ */
+export function buildMediaStory(text: string | undefined, mediaUrl: string | undefined): Story {
+  const story: Story = [];
+  const cleanText = text?.trim() ?? "";
+  const cleanUrl = mediaUrl?.trim() ?? "";
+  
+  // Add text content if present
+  if (cleanText) {
+    story.push(...markdownToStory(cleanText));
+  }
+  
+  // Add image block if URL looks like an image
+  if (cleanUrl && isImageUrl(cleanUrl)) {
+    story.push(createImageBlock(cleanUrl, ""));
+  } else if (cleanUrl) {
+    // For non-image URLs, add as a link
+    story.push({ inline: [{ link: { href: cleanUrl, content: cleanUrl } }] });
+  }
+  
+  return story.length > 0 ? story : [{ inline: [""] }];
+}
diff --git a/extensions/tlon/src/urbit/story.ts b/extensions/tlon/src/urbit/story.ts
index c988a74b1..fffb3c15d 100644
--- a/extensions/tlon/src/urbit/story.ts
+++ b/extensions/tlon/src/urbit/story.ts
@@ -96,6 +96,15 @@ function parseInlineMarkdown(text: string): StoryInline[] {
       continue;
     }
 
+    // Markdown images: ![alt](url)
+    const imageMatch = remaining.match(/^!\[([^\]]*)\]\(([^)]+)\)/);
+    if (imageMatch) {
+      // Return a special marker that will be hoisted to a block
+      result.push({ __image: { src: imageMatch[2], alt: imageMatch[1] } } as unknown as StoryInline);
+      remaining = remaining.slice(imageMatch[0].length);
+      continue;
+    }
+
     // Plain URL detection
     const urlMatch = remaining.match(/^(https?:\/\/[^\s<>"\]]+)/);
     if (urlMatch) {
@@ -144,6 +153,44 @@ function mergeAdjacentStrings(inlines: StoryInline[]): StoryInline[] {
   return result;
 }
 
+/**
+ * Create an image block
+ */
+export function createImageBlock(src: string, alt: string = "", height: number = 0, width: number = 0): StoryVerse {
+  return {
+    block: {
+      image: { src, height, width, alt },
+    },
+  };
+}
+
+/**
+ * Check if URL looks like an image
+ */
+export function isImageUrl(url: string): boolean {
+  const imageExtensions = /\.(jpg|jpeg|png|gif|webp|svg|bmp|ico)(\?.*)?$/i;
+  return imageExtensions.test(url);
+}
+
+/**
+ * Process inlines and extract any image markers into blocks
+ */
+function processInlinesForImages(inlines: StoryInline[]): { inlines: StoryInline[]; imageBlocks: StoryVerse[] } {
+  const cleanInlines: StoryInline[] = [];
+  const imageBlocks: StoryVerse[] = [];
+  
+  for (const inline of inlines) {
+    if (typeof inline === "object" && "__image" in inline) {
+      const img = (inline as unknown as { __image: { src: string; alt: string } }).__image;
+      imageBlocks.push(createImageBlock(img.src, img.alt));
+    } else {
+      cleanInlines.push(inline);
+    }
+  }
+  
+  return { inlines: cleanInlines, imageBlocks };
+}
+
 /**
  * Convert markdown text to Tlon story format
  */
@@ -244,7 +291,14 @@ export function markdownToStory(markdown: string): Story {
           withBreaks.push(inline);
         }
       }
-      story.push({ inline: withBreaks });
+      
+      // Extract any images from inlines and add as separate blocks
+      const { inlines: cleanInlines, imageBlocks } = processInlinesForImages(withBreaks);
+      
+      if (cleanInlines.length > 0) {
+        story.push({ inline: cleanInlines });
+      }
+      story.push(...imageBlocks);
     }
   }