diff --git a/croaker/__init__.py b/croaker/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/croaker/cli.py b/croaker/cli.py
new file mode 100644
index 0000000..58483bb
--- /dev/null
+++ b/croaker/cli.py
@@ -0,0 +1,207 @@
+import io
+import logging
+import os
+import sys
+from pathlib import Path
+from textwrap import dedent
+from typing import List, Optional
+
+import typer
+from dotenv import load_dotenv
+from typing_extensions import Annotated
+
+import croaker.path
+from croaker import client, controller, server
+from croaker.exceptions import ConfigurationError
+from croaker.playlist import Playlist
+
+SETUP_HELP = """
+# Root directory for croaker configuration and logs. See also croaker --root.
+CROAKER_ROOT=~/.dnd/croaker
+
+## COMMAND AND CONTROL WEBSERVER
+
+# Please make sure you set SECRET_KEY in your environment if you are running
+# the command and control webserver. Clients do not need this.
+SECRET_KEY=
+
+# Where the record the webserver daemon's PID
+PIDFILE=~/.dnd/croaker/croaker.pid
+
+# Web interface configuration
+HOST=127.0.0.1
+PORT=8003
+
+## CONTROLLER CLIENT
+
+# The host and port to use when connecting to the websever.
+CONTROLLER_HOST=127.0.0.1
+CONTROLLER_PORT=8003
+
+## MEDIA
+
+# where to store playlist sources
+PLAYLIST_ROOT=~/.dnd/croaker/playlists
+
+# where to cache transcoded media files
+CACHE_ROOT=~/.dnd/croaker/cache
+
+# the kinds of files to add to playlists
+MEDIA_GLOB=*.mp3,*.flac,*.m4a
+
+# If defined, transcode media before streaming it, and cache it to disk. The
+# strings INFILE and OUTFILE will be replaced with the media source file and
+# the cached output location, respectively.
+TRANSCODER=/usr/bin/ffmpeg -i INFILE '-hide_banner -loglevel error -codec:v copy -codec:a libmp3lame -q:a 2' OUTFILE
+
+## LIQUIDSOAP AND ICECAST
+
+# The liquidsoap executable
+LIQUIDSOAP=/usr/bin/liquidsoap
+
+# Icecast2 configuration for Liquidsoap
+ICECAST_PASSWORD=
+ICECAST_MOUNT=
+ICECAST_HOST=
+ICECAST_PORT=
+ICECAST_URL=
+"""
+
+
+app = typer.Typer()
+app_state = {}
+
+
+@app.callback()
+def main(
+    context: typer.Context,
+    root: Optional[Path] = typer.Option(
+        Path("~/.dnd/croaker"),
+        help="Path to the Croaker environment",
+    ),
+    host: Optional[str] = typer.Option(
+        None,
+        help="bind address",
+    ),
+    port: Optional[int] = typer.Option(
+        None,
+        help="bind port",
+    ),
+    debug: Optional[bool] = typer.Option(None, help="Enable debugging output"),
+):
+    load_dotenv(root.expanduser() / Path("defaults"))
+    load_dotenv(stream=io.StringIO(SETUP_HELP))
+    if host:
+        os.environ["HOST"] = host
+    if port:
+        os.environ["PORT"] = port
+    if debug is not None:
+        if debug:
+            os.environ["DEBUG"] = 1
+        else:
+            del os.environ["DEBUG"]
+
+    logging.basicConfig(
+        format="%(message)s",
+        level=logging.DEBUG if debug else logging.INFO,
+    )
+
+    try:
+        croaker.path.media_root()
+        croaker.path.cache_root()
+    except ConfigurationError as e:
+        sys.stderr.write(f"{e}\n\n{SETUP_HELP}")
+        sys.exit(1)
+
+    app_state["client"] = client.Client(
+        host=os.environ["CONTROLLER_HOST"],
+        port=os.environ["CONTROLLER_PORT"],
+    )
+
+    if not context.invoked_subcommand:
+        return play(context)
+
+
+@app.command()
+def setup(context: typer.Context):
+    """
+    (Re)Initialize Croaker.
+    """
+    sys.stderr.write("Interactive setup is not yet available. Sorry!\n")
+    print(dedent(SETUP_HELP))
+
+
+@app.command()
+def start(
+    context: typer.Context,
+    daemonize: bool = typer.Option(True, help="Daemonize the webserver."),
+):
+    """
+    Start the Croaker command and control webserver.
+    """
+    controller.start()
+    if daemonize:
+        server.daemonize()
+    else:
+        server.start()
+
+
+@app.command()
+def stop():
+    """
+    Terminate the webserver process and liquidsoap.
+    """
+    controller.stop()
+    server.stop()
+
+
+@app.command()
+def play(
+    playlist: str = typer.Argument(
+        ...,
+        help="Playlist name",
+    )
+):
+    """
+    Begin playing tracks from the directory $PLAYLIST_ROOT/[NAME].
+    """
+    res = app_state["client"].play(playlist)
+    if res.status_code == 200:
+        print("OK")
+
+
+@app.command()
+def skip():
+    """
+    Play the next track on the current playlist.
+    """
+    res = app_state["client"].skip()
+    if res.status_code == 200:
+        print("OK")
+
+
+@app.command()
+def add(
+    playlist: str = typer.Argument(
+        ...,
+        help="Playlist name",
+    ),
+    theme: Optional[bool] = typer.Option(False, help="Make the first track the theme song."),
+    tracks: Annotated[Optional[List[Path]], typer.Argument()] = None,
+):
+    """
+    Recursively add one or more paths to the specified playlist. Tracks can be
+    any combination of individual audio files and directories containing audio
+    files; anything not already on the playlist will be added to it.
+
+    If --theme is specified, the first track will be designated the playlist
+    "theme." Theme songs get played first whenever the playlist is loaded,
+    after which the playlist order is randomized.
+    """
+    pl = Playlist(name=playlist)
+    pl.add(tracks, make_theme=theme)
+    print(pl)
+
+
+if __name__ == "__main__":
+    app.main()
diff --git a/croaker/client.py b/croaker/client.py
new file mode 100644
index 0000000..f980150
--- /dev/null
+++ b/croaker/client.py
@@ -0,0 +1,43 @@
+import logging
+from dataclasses import dataclass
+from functools import cached_property
+
+import bottle
+import requests
+
+# needs to be imported to attach routes to the default app
+from croaker import routes
+
+assert routes
+
+
+@dataclass
+class Client:
+    host: str
+    port: int
+
+    @cached_property
+    def _session(self):
+        return requests.Session()
+
+    @property
+    def _routes(self):
+        return [r.callback.__name__ for r in bottle.default_app().routes]
+
+    def get(self, uri: str, *args, **params):
+        url = f"http://{self.host}:{self.port}/{uri}"
+        if args:
+            url += "/" + "/".join(args)
+        res = self._session.get(url, params=params)
+        logging.debug(f"{url = }, {res = }")
+        return res
+
+    def __getattr__(self, attr):
+        if attr in self._routes:
+
+            def dispatch(*args, **kwargs):
+                logging.debug(f"calling attr, {args = }, {kwargs = }")
+                return self.get(attr, *args, **kwargs)
+
+            return dispatch
+        return self.__getattribute__(attr)
diff --git a/croaker/controller.py b/croaker/controller.py
new file mode 100644
index 0000000..f5e1525
--- /dev/null
+++ b/croaker/controller.py
@@ -0,0 +1,141 @@
+import logging
+import os
+from pathlib import Path
+from subprocess import Popen
+from time import sleep
+
+from Exscript.protocols import Telnet
+
+from croaker import path
+from croaker.pidfile import pidfile
+from croaker.playlist import Playlist, load_playlist
+
+NOW_PLAYING = None
+
+LIQUIDSOAP_CONFIG = """
+set("server.telnet",true)
+set("request.grace_time", 1.0)
+set("init.daemon.pidfile.path", "{pidfile.path}")
+set("decoder.ffmpeg.codecs.alac", ["alac"])
+
+
+# deeebuggin
+set("log.file.path","{debug_log}")
+
+# set up the stream
+stream = crossfade(normalize(playlist.safe(
+    id='stream',
+    reload_mode='watch',
+    mode='normal',
+    '{playlist_root}/now_playing',
+)))
+
+# if source files don't contain metadata tags, use the filename
+def apply_metadata(m) =
+    title = m["title"]
+    print("Now Playing: #{{m['filename']}}")
+    if (title == "") then
+        [("title", "#{{path.remove_extension(path.basename(m['filename']))}}")]
+    else
+        [("title", "#{{title}}")]
+    end
+end
+
+# apply the metadata parser
+stream = map_metadata(apply_metadata, stream)
+
+# define the source. ignore errors and provide no infallibale fallback. yolo.
+radio = fallback(track_sensitive=false, [stream])
+
+# transcode to icecast
+output.icecast(
+  %mp3.vbr(quality=3),
+  name='Croaker Radio',
+  description='Background music for The Frog Hat Club',
+  host="{icecast_host}",
+  port={icecast_port},
+  password="{icecast_password}",
+  mount="{icecast_mount}",
+  icy_metadata="true",
+  url="{icecast_url}",
+  fallible=true,
+  radio
+)
+"""
+
+
+def generate_liquidsoap_config():
+    log = path.root() / "liquidsoap.log"
+    if log.exists():
+        log.unlink()
+        log.touch()
+    ls_config = path.root() / "croaker.liq"
+    with ls_config.open("wt") as fh:
+        fh.write(
+            LIQUIDSOAP_CONFIG.format(
+                pidfile=_pidfile(terminate_if_running=False),
+                debug_log=log,
+                playlist_root=path.playlist_root(),
+                icecast_host=os.environ.get("ICECAST_HOST"),
+                icecast_port=os.environ.get("ICECAST_PORT"),
+                icecast_mount=os.environ.get("ICECAST_MOUNT"),
+                icecast_password=os.environ.get("ICECAST_PASSWORD"),
+                icecast_url=os.environ.get("ICECAST_URL"),
+            )
+        )
+    path.playlist_root().mkdir(exist_ok=True)
+
+
+def start_liquidsoap():
+    logging.debug("Staring liquidsoap...")
+    pf = _pidfile(terminate_if_running=False)
+    pid = pf.read_pid()
+    if not pid:
+        logging.info("Liquidsoap does not appear to be running. Starting it...")
+        generate_liquidsoap_config()
+        Popen([os.environ["LIQUIDSOAP"], "--daemon", path.root() / "croaker.liq"])
+        sleep(1)
+
+
+def start():
+    play_next("session_start")
+
+
+def stop():
+    _pidfile(terminate_if_running=True)
+
+
+def play_next(playlist_name: str = None):
+    start_liquidsoap()
+    if playlist_name:
+        pl = load_playlist(playlist_name)
+        logging.debug(f"Loaded playlist {pl = }")
+        if NOW_PLAYING != pl.name:
+            _switch_to(pl)
+    _send_liquidsoap_command("skip")
+
+
+def _pidfile(terminate_if_running: bool = True):
+    pf = os.environ.get("LIQUIDSOAP_PIDFILE", None)
+    if pf:
+        pf = Path(pf)
+    else:
+        pf = path.root() / "liquidsoap.pid"
+    return pidfile(pf, terminate_if_running=terminate_if_running)
+
+
+def _switch_to(playlist: Playlist):
+    logging.debug(f"Switching to {playlist = }")
+    np = path.playlist_root() / Path("now_playing")
+    with np.open("wt") as fh:
+        for track in playlist.tracks:
+            fh.write(f"{track}\n")
+    playlist.name
+
+
+def _send_liquidsoap_command(command: str):
+    conn = Telnet()
+    conn.connect("localhost", port=1234)
+    conn.send(f"Croaker_Radio.{command}\r")
+    conn.send("quit\r")
+    conn.close()
diff --git a/croaker/exceptions.py b/croaker/exceptions.py
new file mode 100644
index 0000000..4ecbf84
--- /dev/null
+++ b/croaker/exceptions.py
@@ -0,0 +1,16 @@
+class APIHandlingException(Exception):
+    """
+    An API reqeust could not be encoded or decoded.
+    """
+
+
+class ConfigurationError(Exception):
+    """
+    An error was discovered with the Groove on Demand configuration.
+    """
+
+
+class InvalidPathError(Exception):
+    """
+    The specified path was invalid -- either it was not the expected type or wasn't accessible.
+    """
diff --git a/croaker/path.py b/croaker/path.py
new file mode 100644
index 0000000..3d2b48e
--- /dev/null
+++ b/croaker/path.py
@@ -0,0 +1,47 @@
+import logging
+import os
+from pathlib import Path
+
+from croaker.exceptions import ConfigurationError
+
+_setup_hint = "You may be able to solve this error by running 'croaker setup' or specifying the --root parameter."
+_reinstall_hint = "You might need to reinstall Groove On Demand to fix this error."
+
+
+def root():
+    return Path(os.environ.get("CROAKER_ROOT", "~/.dnd/croaker")).expanduser()
+
+
+def media_root():
+    path = os.environ.get("MEDIA_ROOT", None)
+    if not path:
+        raise ConfigurationError(f"MEDIA_ROOT is not defined in your environment.\n\n{_setup_hint}")
+    path = Path(path).expanduser()
+    if not path.exists() or not path.is_dir():
+        raise ConfigurationError(
+            "The media_root directory (MEDIA_ROOT) doesn't exist, or isn't a directory.\n\n{_setup_hint}"
+        )
+    logging.debug(f"Media root is {path}")
+    return path
+
+
+def cache_root():
+    path = Path(os.environ.get("CACHE_ROOT", root() / Path("cache"))).expanduser()
+    logging.debug(f"Media cache root is {path}")
+    return path
+
+
+def playlist_root():
+    path = Path(os.environ.get("PLAYLIST_ROOT", root() / Path("playlsits"))).expanduser()
+    logging.debug(f"Playlist root is {path}")
+    return path
+
+
+def media(relpath):
+    path = media_root() / Path(relpath)
+    return path
+
+
+def transcoded_media(relpath):
+    path = cache_root() / Path(relpath + ".webm")
+    return path
diff --git a/croaker/pidfile.py b/croaker/pidfile.py
new file mode 100644
index 0000000..4ff4663
--- /dev/null
+++ b/croaker/pidfile.py
@@ -0,0 +1,19 @@
+import logging
+import os
+import signal
+from pathlib import Path
+
+from daemon import pidfile as _pidfile
+
+
+def pidfile(pidfile_path: Path, terminate_if_running: bool = True):
+    pf = _pidfile.TimeoutPIDLockFile(pidfile_path, 30)
+    pid = pf.read_pid()
+    if pid and terminate_if_running:
+        try:
+            logging.debug(f"Stopping PID {pid}")
+            os.kill(pid, signal.SIGTERM)
+        except ProcessLookupError:
+            logging.debug(f"PID {pid} not running; breaking lock.")
+            pf.break_lock()
+    return pf
diff --git a/croaker/playlist.py b/croaker/playlist.py
new file mode 100644
index 0000000..dfd4deb
--- /dev/null
+++ b/croaker/playlist.py
@@ -0,0 +1,86 @@
+import logging
+import os
+from dataclasses import dataclass
+from functools import cached_property
+from itertools import chain
+from pathlib import Path
+from random import shuffle
+from typing import List
+
+import croaker.path
+
+playlists = {}
+
+
+def _stripped(name):
+    name.replace('"', "")
+    name.replace("'", "")
+    return name
+
+
+@dataclass
+class Playlist:
+    name: str
+    theme: Path = Path("_theme.mp3")
+    current_track: int = 0
+
+    @cached_property
+    def path(self):
+        return croaker.path.playlist_root() / Path(self.name)
+
+    @cached_property
+    def tracks(self):
+        if not self.path.exists():
+            raise RuntimeError(f"Playlist {self.name} not found at {self.path}.")
+
+        entries = []
+        theme = self.path / self.theme
+        if theme.exists():
+            entries[0] = theme
+        files = [e for e in self.get_audio_files() if e.name != "_theme.mp3"]
+        if files:
+            shuffle(files)
+            entries += files
+        return entries
+
+    def get_audio_files(self, path: Path = None):
+        if not path:
+            path = self.path
+        logging.debug(f"Getting files matching {os.environ['MEDIA_GLOB']} from {path}")
+        pats = os.environ["MEDIA_GLOB"].split(",")
+        return chain(*[list(path.glob(pat)) for pat in pats])
+
+    def _add_track(self, target: Path, source: Path, make_theme: bool = False):
+        if source.is_dir():
+            for file in self.get_audio_files(source):
+                self._add_track(self.path / _stripped(file.name), file)
+            return
+        if target.exists():
+            if not target.is_symlink():
+                logging.warning(f"{target}: target already exists and is not a symlink; skipping.")
+                return
+            target.unlink()
+        target.symlink_to(source)
+
+    def add(self, tracks: List[Path], make_theme: bool = False):
+        self.path.mkdir(parents=True, exist_ok=True)
+        if make_theme:
+            if source.is_dir():
+                raise RuntimeError(f"Cannot create a playlist theme from a directory: {source}")
+            target = self.path / "_theme.mp3"
+            source = tracks.pop(0)
+            self._add_track(target, source, make_theme=True)
+        for track in tracks:
+            self._add_track(target=self.path / _stripped(track.name), source=track)
+        return sorted(self.get_audio_files())
+
+    def __repr__(self):
+        lines = [f"Playlist {self.name}"]
+        lines += [f" * {track}" for track in self.tracks]
+        return "\n".join(lines)
+
+
+def load_playlist(name: str):
+    if name not in playlists:
+        playlists[name] = Playlist(name=name)
+    return playlists[name]
diff --git a/croaker/routes.py b/croaker/routes.py
new file mode 100644
index 0000000..fa0ccbc
--- /dev/null
+++ b/croaker/routes.py
@@ -0,0 +1,17 @@
+from bottle import route
+
+from croaker import controller
+
+
+@route("/play/<playlist_name>")
+def play(playlist_name=None):
+    if not controller.play_next(playlist_name):
+        return
+    return "OK"
+
+
+@route("/skip")
+def skip():
+    if not controller.play_next():
+        return
+    return "OK"
diff --git a/croaker/server.py b/croaker/server.py
new file mode 100644
index 0000000..e8585a0
--- /dev/null
+++ b/croaker/server.py
@@ -0,0 +1,43 @@
+import logging
+import os
+from pathlib import Path
+
+import bottle
+import daemon
+
+from croaker import path, routes
+from croaker.pidfile import pidfile
+
+assert routes
+app = bottle.default_app()
+
+
+def _pidfile(terminate_if_running: bool = True):
+    pf = os.environ.get("PIDFILE", None)
+    if pf:
+        pf = Path(pf)
+    else:
+        pf = path.root() / "croaker.pid"
+    return pidfile(pf, terminate_if_running=terminate_if_running)
+
+
+def daemonize(host: str = "0.0.0.0", port: int = 8003, debug: bool = False) -> None:  # pragma: no cover
+    logging.info(f"Daemonizing webserver on http://{host}:{port}, pidfile and output in {path.root()}")
+    context = daemon.DaemonContext()
+    context.pidfile = _pidfile()
+    context.stdout = open(path.root() / Path("croaker.out"), "wb")
+    context.stderr = open(path.root() / Path("croaker.err"), "wb", buffering=0)
+    context.open()
+    start(host, port, debug)
+
+
+def stop():
+    _pidfile()
+
+
+def start(host: str = "0.0.0.0", port: int = 8003, debug: bool = False) -> None:  # pragma: no cover
+    """
+    Start the Bottle app.
+    """
+    logging.debug(f"Configuring webserver with host={host}, port={port}, debug={debug}")
+    app.run(host=os.getenv("HOST", host), port=os.getenv("PORT", port), debug=debug, server="paste", quiet=True)
diff --git a/pyproject.toml b/pyproject.toml
new file mode 100644
index 0000000..1750b43
--- /dev/null
+++ b/pyproject.toml
@@ -0,0 +1,54 @@
+[tool.poetry]
+name = "croaker"
+version = "0.1.0"
+description = ""
+authors = ["evilchili <evilchili@gmail.com>"]
+readme = "README.md"
+packages = [
+    { include = "croaker" }
+]
+
+[tool.poetry.dependencies]
+python = "^3.10"
+prompt-toolkit = "^3.0.38"
+typer = "^0.9.0"
+python-dotenv = "^0.21.0"
+rich = "^13.7.0"
+pyyaml = "^6.0.1"
+bottle = "^0.12.25"
+paste = "^3.7.1"
+python-daemon = "^3.0.1"
+requests = "^2.31.0"
+psutil = "^5.9.8"
+exscript = "^2.6.28"
+
+[tool.poetry.scripts]
+croaker = "croaker.cli:app"
+
+[tool.poetry.dev-dependencies]
+black = "^23.3.0"
+isort = "^5.12.0"
+pyproject-autoflake = "^1.0.2"
+
+[tool.black]
+line-length = 120
+target-version = ['py310']
+
+[tool.isort]
+multi_line_output = 3
+line_length = 120
+include_trailing_comma = true
+
+[tool.autoflake]
+check = false                        # return error code if changes are needed
+in-place = true                      # make changes to files instead of printing diffs
+recursive = true                     # drill down directories recursively
+remove-all-unused-imports = true     # remove all unused imports (not just those from the standard library)
+ignore-init-module-imports = true    # exclude __init__.py when removing unused imports
+remove-duplicate-keys = true         # remove all duplicate keys in objects
+remove-unused-variables = true       # remove unused variables
+
+
+[build-system]
+requires = ["poetry-core"]
+build-backend = "poetry.core.masonry.api"