diff --git a/cogs/player/jockey.py b/cogs/player/jockey.py
index b2950e4..5d840ea 100644
--- a/cogs/player/jockey.py
+++ b/cogs/player/jockey.py
@@ -2,7 +2,7 @@
 Music player class for Blanco. Subclass of mafic.Player.
 """
 
-from asyncio import get_event_loop
+from asyncio import get_event_loop, sleep
 from time import time
 from typing import TYPE_CHECKING, List, Optional, Tuple
 
@@ -18,7 +18,8 @@
 from utils.time import human_readable_time
 from views.now_playing import NowPlayingView
 
-from .jockey_helpers import find_lavalink_track, parse_query
+from .jockey_helpers import (find_lavalink_track, invalidate_lavalink_track,
+                             parse_query)
 from .queue import QueueManager
 
 if TYPE_CHECKING:
@@ -196,7 +197,36 @@ async def _play(self, item: 'QueueItem') -> bool:
                 raise RuntimeError(err.args[0]) from err
 
         # Play track
-        await self.play(item.lavalink_track, volume=self.volume)
+        has_retried = False
+        while True:
+            try:
+                await self.play(item.lavalink_track, volume=self.volume)
+            except PlayerNotConnected as err:
+                # If we've already retried, give up
+                if has_retried:
+                    raise JockeyError(err.args[0]) from err
+
+                # Wait until we're connected
+                wait_time = 0
+                self._logger.warning(
+                    'PlayerNotConnected raised while trying to play `%s\', retrying...',
+                    item.title
+                )
+                while not self.connected:
+                    if wait_time >= 10:
+                        raise JockeyError('Timeout while waiting for player to connect') from err
+
+                    # Print wait message only once
+                    if wait_time == 0:
+                        self._logger.debug('Waiting 10 sec for player to connect...')
+                    await sleep(0.1)
+                    wait_time += 0.1
+
+                # Remove cached Lavalink track and try again
+                invalidate_lavalink_track(item)
+                has_retried = True
+            else:
+                break
 
         # We don't want to play if the player is not idle
         # as that will effectively skip the current track.
diff --git a/cogs/player/jockey_helpers.py b/cogs/player/jockey_helpers.py
index 77dfa3d..3bebf34 100644
--- a/cogs/player/jockey_helpers.py
+++ b/cogs/player/jockey_helpers.py
@@ -260,6 +260,38 @@ async def find_lavalink_track( # pylint: disable=too-many-statements
     return lavalink_track
 
 
+def invalidate_lavalink_track(item: QueueItem):
+    """
+    Removes a cached Lavalink track from Redis.
+
+    :param item: The QueueItem to invalidate the track for.
+    """
+    if REDIS is None:
+        return
+
+    # Determine key type
+    redis_key = None
+    redis_key_type = None
+    if item.spotify_id is not None:
+        redis_key = item.spotify_id
+        redis_key_type = 'spotify_id'
+    elif item.isrc is not None:
+        redis_key = item.isrc
+        redis_key_type = 'isrc'
+
+    # Invalidate cached Lavalink track
+    if redis_key is not None and redis_key_type is not None:
+        REDIS.invalidate_lavalink_track(
+            redis_key,
+            key_type=redis_key_type
+        )
+    else:
+        LOGGER.warning(
+            'Could not invalidate cached track for `%s\': no key',
+            item.title
+        )
+
+
 async def parse_query(
     node: 'Node',
     spotify: Spotify,
diff --git a/database/redis.py b/database/redis.py
index 1079a31..a8b2fd0 100644
--- a/database/redis.py
+++ b/database/redis.py
@@ -26,6 +26,15 @@ def __init__(self, host: str, port: int, password: Optional[str] = None):
 
         # Logger
         self._logger = create_logger(self.__class__.__name__)
+        self._logger.debug('Attempting to connect to Redis server...')
+
+        # Test connection
+        try:
+            self._client.ping()
+        except redis.ConnectionError as err:
+            self._logger.critical('Could not connect to Redis server. Check your configuration.')
+            raise RuntimeError('Could not connect to Redis server.') from err
+
         self._logger.info('Connected to Redis server. Enable debug logging to see cache hits.')
 
     def set_lavalink_track(self, key: str, value: str, *, key_type: str):
@@ -52,6 +61,17 @@ def get_lavalink_track(self, key: str, *, key_type: str) -> Optional[str]:
         self._logger.debug('Got cached Lavalink track for %s:%s', key_type, key)
         return self._client.get(f'lavalink:{key_type}:{key}') # type: ignore
 
+    def invalidate_lavalink_track(self, key: str, *, key_type: str):
+        """
+        Removes a cached Lavalink track.
+        
+        :param key: The key to remove the track for.
+        :param key_type: The type of key to remove the track for, e.g. 'isrc' or 'spotify_id'.
+        """
+        self._logger.debug('Invalidating Lavalink track for %s:%s', key_type, key)
+        if self._client.exists(f'lavalink:{key_type}:{key}'):
+            self._client.delete(f'lavalink:{key_type}:{key}')
+
     def set_spotify_track(self, spotify_id: str, track: 'SpotifyTrack'):
         """
         Save a Spotify track.
diff --git a/utils/blanco.py b/utils/blanco.py
index 87b17d2..34786ca 100644
--- a/utils/blanco.py
+++ b/utils/blanco.py
@@ -9,7 +9,7 @@
 from mafic import EndReason, NodePool, VoiceRegion
 from nextcord import (Activity, ActivityType, Forbidden, HTTPException,
                       Interaction, NotFound, PartialMessageable, StageChannel,
-                      TextChannel, Thread, VoiceChannel)
+                      TextChannel, Thread, VoiceChannel, MessageFlags)
 from nextcord.ext.commands import Bot
 
 from cogs.player.jockey_helpers import find_lavalink_track
@@ -488,7 +488,11 @@ async def send_now_playing(self, event: 'TrackStartEvent[Jockey]'):
         current_track = event.player.queue_manager.current
         embed = event.player.now_playing(event.track)
         view = NowPlayingView(self, event.player, current_track.spotify_id)
-        msg = await channel.send(embed=embed, view=view)
+
+        # Send message silently
+        flags = MessageFlags()
+        flags.suppress_notifications = True
+        msg = await channel.send(embed=embed, view=view, flags=flags)
 
         # Save now playing message ID
         self.database.set_now_playing(guild_id, msg.id)