diff --git a/.envrc.sample b/.envrc.sample
index 0b4dae2..6bf1d37 100644
--- a/.envrc.sample
+++ b/.envrc.sample
@@ -1,6 +1,6 @@
+export NODE_OPTIONS=--openssl-legacy-provider # Option for OpenSSL error prevention for libraries in use
 export SLACK_BOT_TOKEN="" # SlackBot OAuth Token
 export DISCORD_BOT_TOKEN="" # DiscordBot OAuth Token
 export DISCORD_SERVER_ID="" # DiscordBot OAuth Token
-export NODE_OPTIONS=--openssl-legacy-provider # Prevent OpenSSL compatibility errors
 export MIGRATE_ARCHIVE="true" # Whether to migrate archive channel
 export SHOW_CUT_LINE="true" # Whether to show cut line between message
diff --git a/command/build/message.mts b/command/build/message.mts
index 2cdc276..04a9718 100644
--- a/command/build/message.mts
+++ b/command/build/message.mts
@@ -71,6 +71,12 @@ interface Options {
     process.exit(0)
   }
   spinner.success()
+  // メッセージに最大ファイルサイズを超えているファイルがある場合は警告を出力する
+  if (buildAllMessageFileResult.isMaxFileSizeOver) {
+    spinner.warning(
+      "Message has attachments that exceed Discord's maximum file size.\nAttachments that exceed Discord's maximum file size will be appended to the message as a file URL.\nConsider releasing the maximum file upload size limit with Discord's server boost."
+    )
+  }
 
   process.exit(0)
 })()
diff --git a/command/deploy/message.mts b/command/deploy/message.mts
index f469351..1f0fad4 100644
--- a/command/deploy/message.mts
+++ b/command/deploy/message.mts
@@ -73,6 +73,12 @@ interface Options {
     process.exit(0)
   }
   spinner.success()
+  // メッセージに最大ファイルサイズを超えているファイルがある場合は警告を出力する
+  if (createAllMessageResult.isMaxFileSizeOver) {
+    spinner.warning(
+      "Message has attachments that exceed Discord's maximum file size.\nAttachments that exceed Discord's maximum file size will be appended to the message as a file URL.\nConsider releasing the maximum file upload size limit with Discord's server boost."
+    )
+  }
 
   process.exit(0)
 })()
diff --git a/libs/channel.mts b/libs/channel.mts
index 637d14c..a88f28f 100644
--- a/libs/channel.mts
+++ b/libs/channel.mts
@@ -19,6 +19,11 @@ export interface Channel {
     channel_name: string
     is_archived: boolean
     is_deleted: boolean
+    guild: {
+      boost_level: 0 | 1 | 2 | 3
+      boost_count: number
+      max_file_size: 8000000 | 50000000 | 100000000
+    }
     topic: string
     message_file_paths: string[]
   }
@@ -119,6 +124,11 @@ export const buildChannelFile = async (
             channel_name: channel.name || "",
             is_archived: channel.is_archived || false,
             is_deleted: false,
+            guild: {
+              boost_level: 0,
+              boost_count: 0,
+              max_file_size: 8000000,
+            },
             topic: channel.purpose?.value ? channel.purpose.value : "",
             message_file_paths: distMessageFilePaths,
           },
@@ -177,13 +187,34 @@ export const createChannel = async (
             ? archiveCategory.id
             : defaultCategory.id,
         })
-        // チャンネルのIDを更新する
-        channel.discord.channel_id = result.id
-        newChannels.push(channel)
+
+        // サーバーブーストレベルとファイルサイズを算出する
+        const boostCount = result.guild.premiumSubscriptionCount || 0
+        let boostLevel: Channel["discord"]["guild"]["boost_level"] = 0
+        if (boostCount >= 2 && boostCount < 7) {
+          boostLevel = 1
+        } else if (boostCount >= 7 && boostCount < 14) {
+          boostLevel = 2
+        } else if (boostCount >= 14) {
+          boostLevel = 3
+        }
+        let maxFileSize: Channel["discord"]["guild"]["max_file_size"] = 8000000
+        if (boostLevel === 2) {
+          maxFileSize = 50000000
+        } else if (boostLevel === 3) {
+          maxFileSize = 100000000
+        }
+
+        const newChannel = { ...channel }
+        newChannel.discord.channel_id = result.id
+        newChannel.discord.guild.boost_level = boostLevel
+        newChannel.discord.guild.boost_count = boostCount
+        newChannel.discord.guild.max_file_size = maxFileSize
+        newChannels.push(newChannel)
       }
     }
 
-    // チャンネルファイルを作成する
+    // チャンネルファイルを更新する
     const createChannelFileResult = await createChannelFile(
       distChannelFilePath,
       newChannels
diff --git a/libs/message.mts b/libs/message.mts
index 67a81ba..38c23b9 100644
--- a/libs/message.mts
+++ b/libs/message.mts
@@ -90,9 +90,11 @@ export const buildMessageFile = async (
   srcMessageFilePath: string,
   distMessageFilePath: string,
   users: User[],
+  maxFileSize: number,
   showCutLine: boolean
 ): Promise<{
   messages: Message[]
+  isMaxFileSizeOver?: boolean
   status: "success" | "failed"
   message?: any
 }> => {
@@ -101,6 +103,7 @@ export const buildMessageFile = async (
     await access(srcMessageFilePath, constants.R_OK)
     const messageFile = await readFile(srcMessageFilePath, "utf8")
     const messages = JSON.parse(messageFile) as SlackMessage[]
+    let isMaxFileSizeOver = false
     for (const message of messages) {
       let text = ""
 
@@ -140,6 +143,9 @@ export const buildMessageFile = async (
 
       // 添付ファイルがあれば追加
       const files: Message["files"] = message.files?.map((file) => {
+        if (file.size && file.size > maxFileSize && !isMaxFileSizeOver) {
+          isMaxFileSizeOver = true
+        }
         return {
           id: file.id || "",
           file_type: file.filetype || "",
@@ -168,7 +174,11 @@ export const buildMessageFile = async (
       }
     }
 
-    return { messages: newMessages, status: "success" }
+    return {
+      messages: newMessages,
+      isMaxFileSizeOver: isMaxFileSizeOver,
+      status: "success",
+    }
   } catch (error) {
     return { messages: [], status: "failed", message: error }
   }
@@ -185,10 +195,12 @@ export const buildAllMessageFile = async (
   users: User[],
   showCutLine: boolean
 ): Promise<{
+  isMaxFileSizeOver?: boolean
   status: "success" | "failed"
   message?: any
 }> => {
   try {
+    let isMaxFileSizeOver = false
     await Promise.all(
       channels.map(
         async (channel) =>
@@ -197,21 +209,28 @@ export const buildAllMessageFile = async (
               async (srcMessageFilePath, index) => {
                 const distMessageFilePath =
                   channel.discord.message_file_paths[index]
-                const { status, message } = await buildMessageFile(
+                const buildMessageFileResult = await buildMessageFile(
                   srcMessageFilePath,
                   distMessageFilePath,
                   users,
+                  channel.discord.guild.max_file_size,
                   showCutLine
                 )
-                if (status === "failed") {
-                  throw new Error(message)
+                if (
+                  buildMessageFileResult.isMaxFileSizeOver &&
+                  !isMaxFileSizeOver
+                ) {
+                  isMaxFileSizeOver = true
+                }
+                if (buildMessageFileResult.status === "failed") {
+                  throw new Error(buildMessageFileResult.message)
                 }
               }
             )
           )
       )
     )
-    return { status: "success" }
+    return { isMaxFileSizeOver: isMaxFileSizeOver, status: "success" }
   } catch (error) {
     return { status: "failed", message: error }
   }
@@ -240,6 +259,7 @@ export const getMessageFilePaths = async (messageDirPath: string) => {
  *  Create message
  * @param discordGuild
  * @param channelId
+ * @param maxFileSize
  * @param distMessageFilePath
  * @param messages
  */
@@ -247,9 +267,11 @@ export const createMessage = async (
   discordGuild: Guild,
   messages: Message[],
   channelId: string,
+  maxFileSize: number,
   distMessageFilePath: string
 ): Promise<{
   messages: Message[]
+  isMaxFileSizeOver?: boolean
   status: "success" | "failed"
   message?: any
 }> => {
@@ -257,9 +279,31 @@ export const createMessage = async (
     // メッセージを作成
     const channelGuild = discordGuild.channels.cache.get(channelId)
     const newMessages: Message[] = []
+    let isMaxFileSizeOver = false
     if (channelGuild && channelGuild.type === ChannelType.GuildText) {
       for (const message of messages) {
-        const result = await channelGuild.send(message.text)
+        /**
+         * サーバーブーストレベルに応じて、最大ファイルサイズを超過したファイルは、
+         * ファイルをアップロードせず、ファイルURLを添付するようにする
+         */
+        const maxSizeOverFileUrls = message.files?.filter(
+          (file) => file.size > maxFileSize
+        )
+        const uploadFileUrls = message.files
+          ?.filter((file) => file.size < maxFileSize)
+          .map((file) => file.url)
+        let content = message.text
+        if (maxSizeOverFileUrls) {
+          isMaxFileSizeOver = true
+          for (const file of maxSizeOverFileUrls) {
+            content += `\n${file.url}`
+          }
+        }
+
+        const result = await channelGuild.send({
+          content: content,
+          files: uploadFileUrls,
+        })
         newMessages.push({
           ...message,
           ...{
@@ -290,7 +334,11 @@ export const createMessage = async (
       }
     }
 
-    return { messages: newMessages, status: "success" }
+    return {
+      messages: newMessages,
+      isMaxFileSizeOver: isMaxFileSizeOver,
+      status: "success",
+    }
   } catch (error) {
     return { messages: [], status: "failed", message: error }
   }
@@ -303,10 +351,12 @@ export const createAllMessage = async (
   discordGuild: Guild,
   channels: Channel[]
 ): Promise<{
+  isMaxFileSizeOver?: boolean
   status: "success" | "failed"
   message?: any
 }> => {
   try {
+    let isMaxFileSizeOver = false
     await Promise.all(
       channels.map(async (channel) => {
         await Promise.all(
@@ -319,16 +369,20 @@ export const createAllMessage = async (
               discordGuild,
               getMessageFileResult.messages,
               channel.discord.channel_id,
+              channel.discord.guild.max_file_size,
               messageFilePath
             )
             if (createMessageResult.status === "failed") {
               throw new Error(createMessageResult.message)
             }
+            if (createMessageResult.isMaxFileSizeOver && !isMaxFileSizeOver) {
+              isMaxFileSizeOver = true
+            }
           })
         )
       })
     )
-    return { status: "success" }
+    return { isMaxFileSizeOver: isMaxFileSizeOver, status: "success" }
   } catch (error) {
     return { status: "failed", message: error }
   }
diff --git a/libs/util/spinner.mts b/libs/util/spinner.mts
index e44476b..fed5cc0 100644
--- a/libs/util/spinner.mts
+++ b/libs/util/spinner.mts
@@ -8,8 +8,9 @@ export class Spinner {
     loading: "⠋⠙⠹⠸⠼⠴⠦⠧⠇⠏",
     success: "✔️",
     failed: "×",
+    warning: "⚠️",
   }
-  private charsType: "loading" | "success" | "failed" = "loading"
+  private charsType: "loading" | "success" | "failed" | "warning" = "loading"
   private charIndex: number = 0
   private delay: number = 60
   private id?: NodeJS.Timer
@@ -29,6 +30,8 @@ export class Spinner {
       char = pc.green(char)
     } else if (this.charsType === "failed") {
       char = pc.red(char)
+    } else if (this.charsType === "warning") {
+      char = pc.yellow(char)
     }
     this.stream.write(char + " " + pc.blue(this.text))
     this.charIndex = (this.charIndex + 1) % chars.length
@@ -54,7 +57,6 @@ export class Spinner {
   success(text?: string | null, message?: any) {
     this.stop()
     if (text) this.text = text
-    if (this.text === "") this.text = "Success"
     this.charsType = "success"
     console.log(pc.green(this.chars.success) + " " + pc.blue(this.text))
     if (message) console.log(message)
@@ -63,9 +65,12 @@ export class Spinner {
   failed(text?: string | null, message?: any) {
     this.stop()
     if (text) this.text = text
-    if (this.text === "") this.text = "Failed"
     this.charsType = "failed"
     console.log(pc.red(this.chars.failed) + " " + pc.blue(this.text))
     if (message) console.error(message)
   }
+
+  warning(text: string) {
+    console.log(pc.yellow(this.chars.warning) + " " + pc.yellow(text))
+  }
 }