diff --git a/royalnet/audio/playmodes.py b/royalnet/audio/playmodes.py
index d9f4e904..6220b0c5 100644
--- a/royalnet/audio/playmodes.py
+++ b/royalnet/audio/playmodes.py
@@ -3,12 +3,19 @@ import random
 
 
 class PlayMode:
+    def __init__(self):
+        self.now_playing = None
+        self.generator = self._generator()
+
+    async def next(self):
+        return await self.generator.__anext__()
+
     def videos_left(self):
         raise NotImplementedError()
 
-    async def next(self):
+    async def _generator(self):
         """Get the next video from the list and advance it."""
-        raise NotImplementedError()
+        yield NotImplemented
 
     def add(self, item):
         """Add a new video to the PlayMode."""
@@ -18,6 +25,7 @@ class PlayMode:
 class Playlist(PlayMode):
     """A video list. Videos played are removed from the list."""
     def __init__(self, starting_list=None):
+        super().__init__()
         if starting_list is None:
             starting_list = []
         self.list = starting_list
@@ -25,14 +33,15 @@ class Playlist(PlayMode):
     def videos_left(self):
         return len(self.list)
 
-    async def next(self):
+    async def _generator(self):
         while True:
             try:
                 next_video = self.list.pop(0)
             except IndexError:
-                yield None
+                self.now_playing = None
             else:
-                yield next_video
+                self.now_playing = next_video
+            yield self.now_playing
 
     def add(self, item):
         self.list.append(item)
@@ -41,6 +50,7 @@ class Playlist(PlayMode):
 class Pool(PlayMode):
     """A video pool. Videos played are played back in random order, and they are kept in the pool."""
     def __init__(self, starting_pool=None):
+        super().__init__()
         if starting_pool is None:
             starting_pool = []
         self.pool = starting_pool
@@ -49,15 +59,17 @@ class Pool(PlayMode):
     def videos_left(self):
         return math.inf
 
-    async def next(self):
+    async def _generator(self):
         while True:
             if self.pool:
+                self.now_playing = None
                 yield None
                 continue
             self._pool_copy = self.pool.copy()
             random.shuffle(self._pool_copy)
             while self._pool_copy:
                 next_video = self._pool_copy.pop(0)
+                self.now_playing = next_video
                 yield next_video
 
     def add(self, item):
diff --git a/royalnet/audio/royalaudiofile.py b/royalnet/audio/royalaudiofile.py
index 806f1ae4..3617f40d 100644
--- a/royalnet/audio/royalaudiofile.py
+++ b/royalnet/audio/royalaudiofile.py
@@ -19,10 +19,10 @@ class RoyalAudioFile(YtdlFile):
     def __init__(self, info: "YtdlInfo", **ytdl_args):
         # Overwrite the new ytdl_args
         self.ytdl_args = {**self.ytdl_args, **ytdl_args}
-        super().__init__(info, outtmpl="%(title)s-%(id)s.%(ext)s", **self.ytdl_args)
+        super().__init__(info, outtmpl="./opusfiles/%(title)s-%(id)s.%(ext)s", **self.ytdl_args)
         # Find the audio_filename with a regex (should be video.opus)
-        self.audio_filename = re.sub(rf"\.{self.info.ext}$", ".mp3", self.video_filename)
-        # Convert the video to mp3
+        self.audio_filename = re.sub(rf"\.{self.info.ext}$", ".opus", self.video_filename)
+        # Convert the video to opus
         # Actually not needed, but we do this anyways for compression reasons
         converter = ffmpeg.input(self.video_filename) \
                           .output(self.audio_filename)
diff --git a/royalnet/bots/discord.py b/royalnet/bots/discord.py
index 50b41255..6f8a3d7f 100644
--- a/royalnet/bots/discord.py
+++ b/royalnet/bots/discord.py
@@ -6,9 +6,9 @@ import sys
 from ..commands import NullCommand
 from ..utils import asyncify, Call, Command
 from ..error import UnregisteredError, NoneFoundError, TooManyFoundError
-from ..network import RoyalnetLink, Message, RequestSuccessful
+from ..network import RoyalnetLink, Message, RequestSuccessful, RequestError
 from ..database import Alchemy, relationshiplinkchain
-from ..audio import RoyalAudioFile
+from ..audio import RoyalAudioFile, PlayMode, Playlist, Pool
 
 loop = asyncio.get_event_loop()
 log = _logging.getLogger(__name__)
@@ -19,9 +19,9 @@ if not discord.opus.is_loaded():
 
 
 class PlayMessage(Message):
-    def __init__(self, url: str, channel_identifier: typing.Optional[typing.Union[int, str]] = None):
+    def __init__(self, url: str, guild_identifier: typing.Optional[str] = None):
         self.url: str = url
-        self.channel_identifier: typing.Optional[typing.Union[int, str]] = channel_identifier
+        self.guild_identifier: typing.Optional[str] = guild_identifier
 
 
 class SummonMessage(Message):
@@ -62,6 +62,8 @@ class DiscordBot:
         self.network: RoyalnetLink = RoyalnetLink(master_server_uri, master_server_secret, "discord",
                                                   self.network_handler)
         loop.create_task(self.network.run())
+        # Create the PlayModes dictionary
+        self.music_data: typing.Dict[discord.Guild, PlayMode] = {}
 
         # noinspection PyMethodParameters
         class DiscordCall(Call):
@@ -86,6 +88,8 @@ class DiscordBot:
 
             async def net_request(call, message: Message, destination: str):
                 response = await self.network.request(message, destination)
+                if isinstance(response, RequestError):
+                    raise response.exc
                 return response
 
             async def get_author(call, error_if_none=False):
@@ -106,6 +110,7 @@ class DiscordBot:
         class DiscordClient(discord.Client):
             @staticmethod
             async def vc_connect_or_move(channel: discord.VoiceChannel):
+                # Connect to voice chat
                 try:
                     await channel.connect()
                 except discord.errors.ClientException:
@@ -116,6 +121,9 @@ class DiscordBot:
                         if voice_client.guild != channel.guild:
                             continue
                         await voice_client.move_to(channel)
+                # Create a music_data entry, if it doesn't exist; default is a Playlist
+                if not self.music_data.get(channel.guild):
+                    self.music_data[channel.guild] = Playlist()
 
             async def on_message(cli, message: discord.Message):
                 text = message.content
@@ -146,7 +154,7 @@ class DiscordBot:
         self.DiscordClient = DiscordClient
         self.bot = self.DiscordClient()
 
-    def find_guild(self, identifier: typing.Union[str, int]):
+    def find_guild(self, identifier: typing.Union[str, int]) -> discord.Guild:
         """Find the Guild with the specified identifier. Names are case-insensitive."""
         if isinstance(identifier, str):
             all_guilds: typing.List[discord.Guild] = self.bot.guilds
@@ -163,7 +171,9 @@ class DiscordBot:
             return self.bot.get_guild(identifier)
         raise TypeError("Invalid identifier type, should be str or int")
 
-    def find_channel(self, identifier: typing.Union[str, int], guild: typing.Optional[discord.Guild] = None):
+    def find_channel(self,
+                     identifier: typing.Union[str, int],
+                     guild: typing.Optional[discord.Guild] = None) -> discord.abc.GuildChannel:
         """Find the GuildChannel with the specified identifier. Names are case-insensitive."""
         if isinstance(identifier, str):
             if guild is not None:
@@ -193,6 +203,13 @@ class DiscordBot:
             return channel
         raise TypeError("Invalid identifier type, should be str or int")
 
+    def find_voice_client(self, guild: discord.Guild):
+        for voice_client in self.bot.voice_clients:
+            voice_client: discord.VoiceClient
+            if voice_client.guild == guild:
+                return voice_client
+        raise NoneFoundError("No voice clients found")
+
     async def network_handler(self, message: Message) -> Message:
         """Handle a Royalnet request."""
         if isinstance(message, SummonMessage):
@@ -208,9 +225,39 @@ class DiscordBot:
         loop.create_task(self.bot.vc_connect_or_move(channel))
         return RequestSuccessful()
 
+    async def add_to_music_data(self, url: str, guild: discord.Guild):
+        """Add a file to the corresponding music_data object."""
+        files: typing.List[RoyalAudioFile] = await asyncify(RoyalAudioFile.create_from_url, url)
+        guild_music_data = self.music_data[guild]
+        for file in files:
+            guild_music_data.add(file)
+        if guild_music_data.now_playing is None:
+            await self.advance_music_data(guild)
+
+    async def advance_music_data(self, guild: discord.Guild):
+        guild_music_data = self.music_data[guild]
+        next_file = await guild_music_data.next()
+        if next_file is None:
+            return
+        voice_client = self.find_voice_client(guild)
+        voice_client.play(next_file.as_audio_source(), after=lambda: loop.create_task(self.advance_music_data(guild)))
+
     async def nh_play(self, message: PlayMessage):
         """Handle a play Royalnet request. That is, add audio to a PlayMode."""
-        raise
+        # Find the matching guild
+        if message.guild_identifier:
+            guild = self.find_guild(message.guild_identifier)
+        else:
+            if len(self.music_data) != 1:
+                raise TooManyFoundError("Multiple guilds found")
+            guild = list(self.music_data)[0]
+        # Ensure the guild has a PlayMode before adding the file to it
+        if not self.music_data.get(guild):
+            # TODO: change Exception
+            raise Exception("No music_data for this guild")
+        # Start downloading
+        loop.create_task(self.add_to_music_data(message.url, guild))
+        return RequestSuccessful()
 
     async def run(self):
         await self.bot.login(self.token)
diff --git a/royalnet/bots/telegram.py b/royalnet/bots/telegram.py
index cf45ab72..0ecc2ed9 100644
--- a/royalnet/bots/telegram.py
+++ b/royalnet/bots/telegram.py
@@ -5,8 +5,8 @@ import logging as _logging
 import sys
 from ..commands import NullCommand
 from ..utils import asyncify, Call, Command
-from royalnet.error import UnregisteredError
-from ..network import RoyalnetLink, Message
+from ..error import UnregisteredError
+from ..network import RoyalnetLink, Message, RequestError
 from ..database import Alchemy, relationshiplinkchain
 
 loop = asyncio.get_event_loop()
@@ -71,6 +71,8 @@ class TelegramBot:
 
             async def net_request(call, message: Message, destination: str):
                 response = await self.network.request(message, destination)
+                if isinstance(response, RequestError):
+                    raise response.exc
                 return response
 
             async def get_author(call, error_if_none=False):
diff --git a/royalnet/commands/play.py b/royalnet/commands/play.py
index 5910840b..02851695 100644
--- a/royalnet/commands/play.py
+++ b/royalnet/commands/play.py
@@ -7,11 +7,11 @@ from ..bots.discord import PlayMessage
 class PlayCommand(Command):
     command_name = "play"
     command_description = "Riproduce una canzone in chat vocale."
-    command_syntax = "(url)"
+    command_syntax = "[ [guild] ] (url)"
 
     @classmethod
     async def common(cls, call: Call):
-        url: str = call.args[0]
-        response: typing.Union[RequestSuccessful, RequestError] = await call.net_request(PlayMessage(url), "discord")
+        guild, url = call.args.match(r"(?:\[(.+)])?\s*(\S+)\s*")
+        response: typing.Union[RequestSuccessful, RequestError] = await call.net_request(PlayMessage(url, guild), "discord")
         response.raise_on_error()
         await call.reply(f"✅ Richiesta la riproduzione di [c]{url}[/c].")
diff --git a/royalnet/commands/reminder.py b/royalnet/commands/reminder.py
index cae785f8..bfc90adc 100644
--- a/royalnet/commands/reminder.py
+++ b/royalnet/commands/reminder.py
@@ -12,9 +12,7 @@ class ReminderCommand(Command):
 
     @classmethod
     async def common(cls, call: Call):
-        match = call.args.match(r"\[ *(.+?) *] *(.+?) *$")
-        date_str = match.group(1)
-        reminder_text = match.group(2)
+        date_str, reminder_text = call.args.match(r"\[ *(.+?) *] *(.+?) *$")
         date: typing.Optional[datetime.datetime]
         try:
             date = dateparser.parse(date_str)
diff --git a/royalnet/utils/command.py b/royalnet/utils/command.py
index cdb8cec3..399b8595 100644
--- a/royalnet/utils/command.py
+++ b/royalnet/utils/command.py
@@ -28,12 +28,12 @@ class CommandArgs(list):
             raise InvalidInputError("Not enough arguments")
         return " ".join(self)
 
-    def match(self, pattern: typing.Pattern) -> typing.Match:
+    def match(self, pattern: typing.Pattern) -> typing.Sequence[typing.AnyStr]:
         text = self.joined()
         match = re.match(pattern, text)
         if match is None:
             raise InvalidInputError("Pattern didn't match")
-        return match
+        return match.groups()
 
     def optional(self, index: int, default=None) -> typing.Optional:
         try: