diff --git a/ryan/utils/messages.py b/ryan/utils/messages.py
index fc6bb13..38e3504 100644
--- a/ryan/utils/messages.py
+++ b/ryan/utils/messages.py
@@ -1,19 +1,20 @@
+import logging
 import random
+import typing as t
 from datetime import datetime
 
 import discord
 
 from ryan.constants import Images
 
-title_success = (
+TITLE_SUCCESS = (
     "Good point",
     "Great moves Ethan",
     "Keep it up",
     "Life is excellent!",
     "The daemon congratulates you",
 )
-
-title_error = (
+TITLE_ERROR = (
     "Galooned again",
     "Put on full blast",
     "Reduced you to memes",
@@ -23,47 +24,70 @@
     "I hold my head",
 )
 
+log = logging.getLogger(__name__)
+
 
-def msg_success(message: str) -> discord.Embed():
+def msg_success(message: str) -> discord.Embed:
     """Create a success embed with `message`."""
     embed = discord.Embed(
         description=message,
         colour=discord.Colour.green(),
     )
-    embed.set_author(name=random.choice(title_success), icon_url=Images.gm_creepy)
+    embed.set_author(name=random.choice(TITLE_SUCCESS), icon_url=Images.gm_creepy)
     return embed
 
 
-def msg_error(message: str) -> discord.Embed():
+def msg_error(message: str) -> discord.Embed:
     """Create an error embed with `message`."""
     embed = discord.Embed(
         description=message,
         colour=discord.Colour.red(),
     )
-    embed.set_author(name=random.choice(title_error), icon_url=Images.gm_creepy)
+    embed.set_author(name=random.choice(TITLE_ERROR), icon_url=Images.gm_creepy)
     return embed
 
 
+async def download_file(attachment: discord.Attachment) -> t.Optional[discord.File]:
+    """
+    Download & return `attachment` file.
+
+    If the download fails, the reason is logged and None will be returned.
+    """
+    log.debug(f"Attempting to download attachment: {attachment.url}")
+    try:
+        return await attachment.to_file()
+    except discord.HTTPException as http_exc:
+        log.warning("Failed to download attachment!", exc_info=http_exc)
+
+
 async def relay_message(message: discord.Message, target: discord.TextChannel) -> None:
-    """Relays a quote embed to the `target` channel."""
-    author = message.author
+    """
+    Relays an embed quoting `message` to the `target` channel.
+
+    If the `message` contains attachments, the first one will be sent with the quotation.
+    User-sent messages do not normally contain multiple attachments, so this case is ignored.
+    """
+    author = message.author  # For short since we'll access this a lot
+    log.debug(f"Building quotation embed for message from: {author}")
+
     if author.display_name != author.name:
         name = f"{author.display_name} ({author.name})"
     else:
         name = author.name
 
-    quote_embed = discord.Embed(description=message.content)
-    quote_embed.set_author(
-        name=name,
-        icon_url=author.avatar_url
-    )
-    quote_embed.set_footer(
-        text=f"{datetime.now()} - {message.guild.name} - {message.channel.name}"
-    )
+    quote_embed = discord.Embed(description=message.content, timestamp=datetime.utcnow())
+    quote_embed.set_author(name=name, icon_url=author.avatar_url)
+    quote_embed.set_footer(text=f"{message.guild.name} | {message.channel.name}")
+
     if message.attachments:
-        quote_embed.add_field(
-            name="Attachments:",
-            value="\n".join(message.attachments)
-        )
+        log.debug(f"Relaying first of {len(message.attachments)} attachments")
+        attachment = message.attachments[0]  # We will only relay the first attachment
+
+        if (att_file := await download_file(attachment)) is not None:
+            quote_embed.set_image(url=f"attachment://{attachment.filename}")  # Embed displays the attached file
+    else:
+        log.debug("Message contains no attachments")
+        att_file = None
 
-    await target.send(embed=quote_embed)
+    log.debug("Dispatching quotation embed")
+    await target.send(embed=quote_embed, file=att_file)