diff --git a/src/connection_monitor.rs b/src/connection_monitor.rs
new file mode 100644
index 0000000..df25eef
--- /dev/null
+++ b/src/connection_monitor.rs
@@ -0,0 +1,147 @@
+use serenity::{model::channel::Message, prelude::Context, all::{CreateMessage, CreateEmbed}};
+use std::time::Duration;
+use tokio::time;
+use tracing::{error, info, warn};
+
+use crate::data::{DatabaseClientData, TTSData};
+
+/// Connection monitor that periodically checks voice channel connections
+pub struct ConnectionMonitor;
+
+impl ConnectionMonitor {
+    /// Start the connection monitoring task
+    pub fn start(ctx: Context) {
+        tokio::spawn(async move {
+            info!("Starting connection monitor with 5s interval");
+            let mut interval = time::interval(Duration::from_secs(5));
+
+            loop {
+                interval.tick().await;
+                Self::check_connections(&ctx).await;
+            }
+        });
+    }
+
+    /// Check all active TTS instances and their voice channel connections
+    async fn check_connections(ctx: &Context) {
+        let storage_lock = {
+            let data_read = ctx.data.read().await;
+            data_read
+                .get::<TTSData>()
+                .expect("Cannot get TTSStorage")
+                .clone()
+        };
+
+        let database = {
+            let data_read = ctx.data.read().await;
+            data_read
+                .get::<DatabaseClientData>()
+                .expect("Cannot get DatabaseClientData")
+                .clone()
+        };
+
+        let mut storage = storage_lock.write().await;
+        let mut guilds_to_remove = Vec::new();
+
+        for (guild_id, instance) in storage.iter() {
+            // Check if bot is still connected to voice channel
+            let manager = match songbird::get(ctx).await {
+                Some(manager) => manager,
+                None => {
+                    error!("Cannot get songbird manager");
+                    continue;
+                }
+            };
+
+            let call = manager.get(*guild_id);
+            let is_connected = if let Some(call) = call {
+                if let Some(connection) = call.lock().await.current_connection() {
+                    connection.channel_id.is_some()
+                } else {
+                    false
+                }
+            } else {
+                false
+            };
+
+            if !is_connected {
+                warn!("Bot disconnected from voice channel in guild {}", guild_id);
+
+                // Check if there are users in the voice channel
+                let should_reconnect = match Self::check_voice_channel_users(ctx, instance).await {
+                    Ok(has_users) => has_users,
+                    Err(_) => {
+                        // If we can't check users, don't reconnect
+                        false
+                    }
+                };
+
+                if should_reconnect {
+                    // Try to reconnect
+                    match instance.reconnect(ctx, true).await {
+                        Ok(_) => {
+                            info!(
+                                "Successfully reconnected to voice channel in guild {}",
+                                guild_id
+                            );
+                            
+                            // Send notification message to text channel with embed
+                            let embed = CreateEmbed::new()
+                                .title("🔄 自動再接続しました")
+                                .description("読み上げを停止したい場合は `/stop` コマンドを使用してください。")
+                                .color(0x00ff00);
+                            if let Err(e) = instance.text_channel.send_message(&ctx.http, CreateMessage::new().embed(embed)).await {
+                                error!("Failed to send reconnection message to text channel: {}", e);
+                            }
+                        }
+                        Err(e) => {
+                            error!(
+                                "Failed to reconnect to voice channel in guild {}: {}",
+                                guild_id, e
+                            );
+                            guilds_to_remove.push(*guild_id);
+                        }
+                    }
+                } else {
+                    info!(
+                        "No users in voice channel, removing instance for guild {}",
+                        guild_id
+                    );
+                    guilds_to_remove.push(*guild_id);
+                }
+            }
+        }
+
+        // Remove disconnected instances
+        for guild_id in guilds_to_remove {
+            storage.remove(&guild_id);
+
+            // Remove from database
+            if let Err(e) = database.remove_tts_instance(guild_id).await {
+                error!("Failed to remove TTS instance from database: {}", e);
+            }
+
+            // Ensure bot leaves voice channel
+            if let Some(manager) = songbird::get(ctx).await {
+                let _ = manager.remove(guild_id).await;
+            }
+        }
+    }
+
+    /// Check if there are users in the voice channel
+    async fn check_voice_channel_users(
+        ctx: &Context,
+        instance: &crate::tts::instance::TTSInstance,
+    ) -> Result<bool, Box<dyn std::error::Error + Send + Sync>> {
+        let channels = instance.guild.channels(&ctx.http).await?;
+
+        if let Some(channel) = channels.get(&instance.voice_channel) {
+            let members = channel.members(&ctx.cache)?;
+            let user_count = members.iter().filter(|member| !member.user.bot).count();
+            Ok(user_count > 0)
+        } else {
+            // Channel doesn't exist anymore
+            Ok(false)
+        }
+    }
+}
diff --git a/src/events/ready.rs b/src/events/ready.rs
index f22b410..c2dbb37 100644
--- a/src/events/ready.rs
+++ b/src/events/ready.rs
@@ -5,7 +5,10 @@ use serenity::{
 };
 use tracing::info;
 
-use crate::data::{DatabaseClientData, TTSData};
+use crate::{
+    connection_monitor::ConnectionMonitor,
+    data::{DatabaseClientData, TTSData},
+};
 
 #[tracing::instrument]
 pub async fn ready(ctx: Context, ready: Ready) {
@@ -35,6 +38,9 @@ pub async fn ready(ctx: Context, ready: Ready) {
 
     // Restore TTS instances from database
     restore_tts_instances(&ctx).await;
+
+    // Start connection monitor
+    ConnectionMonitor::start(ctx.clone());
 }
 
 /// Restore TTS instances from database and reconnect to voice channels
@@ -107,7 +113,7 @@ async fn restore_tts_instances(ctx: &Context) {
                 }
 
                 // Try to reconnect to voice channel
-                match instance.reconnect(ctx).await {
+                match instance.reconnect(ctx, true).await {
                     Ok(_) => {
                         // Add to in-memory storage
                         let mut tts_data = tts_data.write().await;
diff --git a/src/main.rs b/src/main.rs
index 35fad26..9de9d17 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -1,5 +1,6 @@
 mod commands;
 mod config;
+mod connection_monitor;
 mod data;
 mod database;
 mod event_handler;
diff --git a/src/tts/instance.rs b/src/tts/instance.rs
index 786ea53..fd44034 100644
--- a/src/tts/instance.rs
+++ b/src/tts/instance.rs
@@ -31,18 +31,40 @@ impl TTSInstance {
         }
     }
 
+    pub async fn check_connection(&self, ctx: &Context) -> bool {
+        let manager = match songbird::get(ctx).await {
+            Some(manager) => manager,
+            None => {
+                tracing::error!("Cannot get songbird manager");
+                return false;
+            }
+        };
+
+        let call = manager.get(self.guild);
+        if let Some(call) = call {
+            if let Some(connection) = call.lock().await.current_connection() {
+                connection.channel_id.is_some()
+            } else {
+                false
+            }
+        } else {
+            false
+        }
+    }
+
     /// Reconnect to the voice channel after bot restart
     #[tracing::instrument]
     pub async fn reconnect(
         &self,
         ctx: &Context,
+        skip_check: bool,
     ) -> Result<(), Box<dyn std::error::Error + Send + Sync>> {
         let manager = songbird::get(&ctx)
             .await
             .ok_or("Songbird manager not available")?;
 
         // Check if we're already connected
-        if manager.get(self.guild).is_some() {
+        if self.check_connection(&ctx).await {
             tracing::info!("Already connected to guild {}", self.guild);
             return Ok(());
         }