diff --git a/src/discord_tools/message.py b/src/discord_tools/message.py
index feaf0cd..92f0088 100644
--- a/src/discord_tools/message.py
+++ b/src/discord_tools/message.py
@@ -1,9 +1,15 @@
 import math
 import os
+from tkinter.tix import IMAGE
+from turtle import Turtle
+from typing import List
 
 import discord
+from idna import intranges_contain
 
 TIPS_MESSAGE = ":bulb: TIPS: You can disable Discord's default preview for link by wrapping it around `<` `>`"
+IMAGE_NBR_LIMIT = 10
+DEFAULT_UPLOAD_SIZE_LIMIT = 209715200
 
 
 async def send_message(message: discord.Message, files, tmp_dir: str, muted: bool):
@@ -11,23 +17,29 @@ async def send_message(message: discord.Message, files, tmp_dir: str, muted: boo
     for file in files:
         joined = os.path.join(tmp_dir, file)
         to_send_files.append(discord.File(joined, file))
-    if len(to_send_files) > 10:
-        first = True
-        while len(to_send_files) > 10:
-            splited_file = to_send_files[:10]
-            to_send_files = to_send_files[10:]
-            if first:
-                await message.reply(
-                    files=splited_file, content=(TIPS_MESSAGE if not muted else None)
-                )
-                first = False
-            else:
-                await message.channel.send(files=splited_file)
-        await message.channel.send(files=to_send_files)
-    else:
-        await message.reply(
-            files=to_send_files, content=(TIPS_MESSAGE if not muted else None)
-        )
+
+    upload_size_limit = (
+        message.guild.filesize_limit
+        if message.guild is not None
+        else DEFAULT_UPLOAD_SIZE_LIMIT
+    )
+    first = True
+    while len(to_send_files) > 0:
+        nbr_file_to_send = get_max_files_number(to_send_files, upload_size_limit)
+        splited_file = to_send_files[:nbr_file_to_send]
+        to_send_files = to_send_files[nbr_file_to_send:]
+        if first and nbr_file_to_send <= 0:
+            return
+        elif nbr_file_to_send <= 0:
+            # Next file is to big to be sent, skip it
+            to_send_files = to_send_files[1:]
+        elif first:
+            await message.reply(
+                files=splited_file, content=(TIPS_MESSAGE if not muted else None)
+            )
+            first = False
+        else:
+            await message.channel.send(files=splited_file)  # type: ignore
 
 
 async def send_command_reply(
@@ -43,23 +55,48 @@ async def send_command_reply(
     for file in files:
         joined = os.path.join(tmp_dir, file)
         to_send_files.append(discord.File(joined, file))
-    if len(to_send_files) > 10:
-        if interaction.channel is not None:
-            first = True
-            while len(to_send_files) > 10:
-                splited_file = to_send_files[:10]
-                to_send_files = to_send_files[10:]
-                if first:
-                    await interaction.followup.send(
-                        files=splited_file,
-                        content=f"{title} - Submited by {author.mention} - <{url}> {chr(10) + TIPS_MESSAGE if not muted else ''}",
-                    )
-                    first = False
-                else:
-                    await interaction.channel.send(files=splited_file)  # type: ignore
-            await interaction.channel.send(files=to_send_files)  # type: ignore
-    else:
-        await interaction.followup.send(
-            files=to_send_files,
-            content=f"{title} - Submited by {author.mention} - <{url}> {chr(10) + TIPS_MESSAGE if not muted else ''}",
-        )
+
+    upload_size_limit = (
+        interaction.guild.filesize_limit
+        if interaction.guild is not None
+        else DEFAULT_UPLOAD_SIZE_LIMIT
+    )
+
+    first = True
+    while len(to_send_files) > 0:
+        nbr_file_to_send = get_max_files_number(to_send_files, upload_size_limit)
+        splited_file = to_send_files[:nbr_file_to_send]
+        to_send_files = to_send_files[nbr_file_to_send:]
+        if first and nbr_file_to_send <= 0:
+            await interaction.followup.send(
+                content=f"This image exceeds upload file size limit", ephemeral=True
+            )
+        elif nbr_file_to_send <= 0:
+            # Next file is to big to be sent, skip it
+            to_send_files = to_send_files[1:]
+        elif first:
+            await interaction.followup.send(
+                files=splited_file,
+                content=f"{title} - Submited by {author.mention} - <{url}> {chr(10) + TIPS_MESSAGE if not muted else ''}",
+            )
+            first = False
+        else:
+            await interaction.channel.send(files=splited_file)  # type: ignore
+
+
+def get_max_files_number(files: List[discord.File], size_limit: int):
+    size = 0
+    nbr = 0
+    for file in files:
+        size = size + os.path.getsize(file.fp.name)  # type: ignore
+        nbr = nbr + 1
+        if nbr >= IMAGE_NBR_LIMIT and size < size_limit:
+            return IMAGE_NBR_LIMIT
+        elif size > size_limit:
+            # We exceeds size limit, remove one image
+            if nbr >= IMAGE_NBR_LIMIT:
+                return IMAGE_NBR_LIMIT - 1
+            else:
+                return nbr - 1
+    # We didn't reach any limit
+    return nbr
diff --git a/src/pixiv/pixiv_api.py b/src/pixiv/pixiv_api.py
index bed34e1..0a507e7 100644
--- a/src/pixiv/pixiv_api.py
+++ b/src/pixiv/pixiv_api.py
@@ -8,7 +8,7 @@ from typing import List, Tuple, Union
 import pixivpy3
 
 cpu_count = os.cpu_count()
-max_thread_num = cpu_count * 4 if cpu_count is not None else 4
+max_thread_num = cpu_count * 2 if cpu_count is not None else 4
 
 
 def dowload_pixiv_images(
@@ -73,5 +73,5 @@ def download_thread(q: Queue[Union[Tuple[str, str, pixivpy3.AppPixivAPI], None]]
         (url, dest_folder, api) = data
         logging.debug(f"[{thread_name}] - Downloading {url}...")
         api.download(url=url, path=dest_folder)
-        logging.debug(f"[{thread_name}] - ... Done")
+        print(f"[{thread_name}] - ... Done")
         q.task_done()