diff --git a/apps/bot/src/whatsapp/sender.ts b/apps/bot/src/whatsapp/sender.ts
index 413527a..0356c4b 100644
--- a/apps/bot/src/whatsapp/sender.ts
+++ b/apps/bot/src/whatsapp/sender.ts
@@ -1,11 +1,9 @@
-import type { WASocket } from "@whiskeysockets/baileys";
+import { readFile, stat } from "node:fs/promises";
+import type { WASocket, AnyMessageContent } from "@whiskeysockets/baileys";
 import pino from "pino";
 
 const logger = pino({ name: "sender" });
 
-// Internal Baileys method used to fetch pre-key bundles and establish individual
-// libsignal sessions for a list of JIDs. Not part of the public type, but it's
-// the only way to avoid "No sessions" on the first group send after pairing.
 type SocketWithAssertSessions = WASocket & {
   assertSessions?: (jids: string[], force: boolean) => Promise<boolean>;
 };
@@ -14,19 +12,10 @@ const CHUNK_SIZE = 5;
 
 async function chunked<T>(items: T[], size: number): Promise<T[][]> {
   const out: T[][] = [];
-  for (let i = 0; i < items.length; i += size) {
-    out.push(items.slice(i, i + size));
-  }
+  for (let i = 0; i < items.length; i += size) out.push(items.slice(i, i + size));
   return out;
 }
 
-/**
- * Establish per-participant libsignal sessions in small chunks. WhatsApp's
- * pre-key endpoint returns 406 "not-acceptable" if any single JID in the
- * batch is in a broken state (deleted account, deactivated, etc.) — so we
- * chunk the work and tolerate per-chunk failures rather than letting one
- * bad participant poison the whole send.
- */
 async function ensureSessionsForGroup(
   socket: WASocket,
   groupJid: string,
@@ -39,44 +28,73 @@ async function ensureSessionsForGroup(
   }
   let ok = 0;
   let failed = 0;
-  const chunks = await chunked(participantJids, CHUNK_SIZE);
-  for (const chunk of chunks) {
+  for (const chunk of await chunked(participantJids, CHUNK_SIZE)) {
     try {
       await internal.assertSessions(chunk, true);
       ok += chunk.length;
     } catch (err) {
       failed += chunk.length;
-      logger.warn(
-        { groupJid, chunkSize: chunk.length, err: (err as Error).message },
-        "assertSessions chunk failed; continuing",
-      );
+      logger.warn({ groupJid, err: (err as Error).message }, "assertSessions chunk failed");
     }
   }
-  logger.info(
-    { groupJid, ok, failed, total: participantJids.length },
-    "ensureSessionsForGroup: done",
-  );
   return { ok, failed, total: participantJids.length };
 }
 
+async function sendWithRetry(
+  socket: WASocket,
+  groupJid: string,
+  content: AnyMessageContent,
+): Promise<{ messageId: string | undefined }> {
+  await ensureSessionsForGroup(socket, groupJid);
+  try {
+    const result = await socket.sendMessage(groupJid, content);
+    return { messageId: result?.key?.id ?? undefined };
+  } catch (err) {
+    const message = (err as Error)?.message ?? "";
+    if (message.includes("No sessions")) {
+      await new Promise((r) => setTimeout(r, 2000));
+      await ensureSessionsForGroup(socket, groupJid);
+      const result = await socket.sendMessage(groupJid, content);
+      return { messageId: result?.key?.id ?? undefined };
+    }
+    throw err;
+  }
+}
+
 export async function sendTextToGroup(
   socket: WASocket,
   groupJid: string,
   text: string,
 ): Promise<{ messageId: string | undefined }> {
-  await ensureSessionsForGroup(socket, groupJid);
-
-  try {
-    const result = await socket.sendMessage(groupJid, { text });
-    return { messageId: result?.key?.id ?? undefined };
-  } catch (err) {
-    const message = (err as Error)?.message ?? "";
-    if (message.includes("No sessions")) {
-      await new Promise((resolve) => setTimeout(resolve, 2000));
-      await ensureSessionsForGroup(socket, groupJid);
-      const result = await socket.sendMessage(groupJid, { text });
-      return { messageId: result?.key?.id ?? undefined };
-    }
-    throw err;
-  }
+  return sendWithRetry(socket, groupJid, { text });
+}
+
+export type MediaKind = "image" | "video" | "document";
+
+export async function sendMediaToGroup(
+  socket: WASocket,
+  groupJid: string,
+  kind: MediaKind,
+  filePath: string,
+  options: { caption?: string; mimeType?: string; filename?: string } = {},
+): Promise<{ messageId: string | undefined }> {
+  // Validate the file exists and read into a buffer. For very large files
+  // (>50MB) Baileys also accepts a stream, but for our reminder use case
+  // files are typically <30MB which fits comfortably in memory.
+  await stat(filePath);
+  const buffer = await readFile(filePath);
+
+  const content: AnyMessageContent =
+    kind === "image"
+      ? { image: buffer, caption: options.caption, mimetype: options.mimeType }
+      : kind === "video"
+      ? { video: buffer, caption: options.caption, mimetype: options.mimeType }
+      : {
+          document: buffer,
+          caption: options.caption,
+          fileName: options.filename ?? "file",
+          mimetype: options.mimeType ?? "application/octet-stream",
+        };
+
+  return sendWithRetry(socket, groupJid, content);
 }