diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9b17979c60..191ceb258b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -35,11 +35,11 @@ v3.10 adds group conversations while resolving other bugs and QOL changes. It is
 ### Breaking
 
 - `Thread.recipient` (`str`) is now `Thread.recipients` (`List[str]`).
-- `Thread.reply` now returns mod_message, user_message1, user_message2... It is no longer limited at a size 2 tuple.
+- `Thread.reply` now returns `mod_message, user_message1, user_message2`... It is no longer limited at a size 2 tuple.
 
 ### Added
 
-- Ability to have group conversations. ([GH #143](https://github.com/kyb3r/modmail/issues/143))
+- Ability to have group conversations with up to 5 users. ([GH #143](https://github.com/kyb3r/modmail/issues/143))
 - Snippets are invoked case insensitively. ([GH #3077](https://github.com/kyb3r/modmail/issues/3077), [PR #3080](https://github.com/kyb3r/modmail/pull/3080))
 - Default tags now use top hoisted role. ([GH #3014](https://github.com/kyb3r/modmail/issues/3014))
 - New thread-related config - `thread_show_roles`, `thread_show_account_age`, `thread_show_join_age`, `thread_cancelled`, `thread_creation_contact_title`, `thread_creation_self_contact_response`, `thread_creation_contact_response`. ([GH #3072](https://github.com/kyb3r/modmail/issues/3072))
diff --git a/cogs/modmail.py b/cogs/modmail.py
index 42eb297a6d..b071cfc8ff 100644
--- a/cogs/modmail.py
+++ b/cogs/modmail.py
@@ -725,6 +725,16 @@ async def adduser(self, ctx, *users_arg: Union[discord.Member, discord.Role, str
             ctx.command.reset_cooldown(ctx)
             return
 
+        if len(users + ctx.thread.recipients) > 5:
+            em = discord.Embed(
+                title="Error",
+                description="Only 5 users are allowed in a group conversation",
+                color=self.bot.error_color,
+            )
+            await ctx.send(embed=em)
+            ctx.command.reset_cooldown(ctx)
+            return
+
         if not silent:
             description = self.bot.formatter.format(
                 self.bot.config["private_added_to_group_response"], moderator=ctx.author
@@ -1327,14 +1337,14 @@ async def edit(self, ctx, message_id: Optional[int] = None, *, message: str):
     @checks.has_permissions(PermissionLevel.REGULAR)
     async def selfcontact(self, ctx):
         """Creates a thread with yourself"""
-        await ctx.invoke(self.contact, user=ctx.author)
+        await ctx.invoke(self.contact, users=[ctx.author])
 
     @commands.command(usage="<user> [category] [options]")
     @checks.has_permissions(PermissionLevel.SUPPORTER)
     async def contact(
         self,
         ctx,
-        user: Union[discord.Member, discord.User],
+        users: commands.Greedy[Union[discord.Member, discord.User, discord.Role]],
         *,
         category: Union[SimilarCategoryConverter, str] = None,
         manual_trigger=True,
@@ -1346,7 +1356,8 @@ async def contact(
         will be created in that specified category.
 
         `category`, if specified, may be a category ID, mention, or name.
-        `user` may be a user ID, mention, or name.
+        `users` may be a user ID, mention, or name. If multiple users are specified, a group thread will start.
+        A maximum of 5 users are allowed.
         `options` can be `silent` or `silently`.
         """
         silent = False
@@ -1371,74 +1382,97 @@ async def contact(
             if isinstance(category, str):
                 category = None
 
-        if user.bot:
-            embed = discord.Embed(color=self.bot.error_color, description="Cannot start a thread with a bot.")
-            return await ctx.send(embed=embed, delete_after=3)
+        errors = []
+        for u in list(users):
+            if isinstance(u, discord.Role):
+                users += u.members
+                users.remove(u)
+
+        for u in list(users):
+            exists = await self.bot.threads.find(recipient=u)
+            if exists:
+                errors.append(f"A thread for {u} already exists.")
+                if exists.channel:
+                    errors[-1] += f" in {exists.channel.mention}"
+                errors[-1] += "."
+                users.remove(u)
+            elif u.bot:
+                errors.append(f"{u} is a bot, cannot add to thread.")
+                users.remove(u)
+            elif await self.bot.is_blocked(u):
+                ref = f"{u.mention} is" if ctx.author != u else "You are"
+                errors.append(f"{ref} currently blocked from contacting {self.bot.user.name}.")
+                users.remove(u)
 
-        exists = await self.bot.threads.find(recipient=user)
-        if exists:
-            desc = "A thread for this user already exists"
-            if exists.channel:
-                desc += f" in {exists.channel.mention}"
-            desc += "."
-            embed = discord.Embed(color=self.bot.error_color, description=desc)
-            await ctx.channel.send(embed=embed, delete_after=3)
+        if len(users) > 5:
+            errors.append("Group conversations only support 5 users.")
+            users = []
 
-        else:
-            creator = ctx.author if manual_trigger else user
-            if await self.bot.is_blocked(user):
-                if not manual_trigger:  # react to contact
-                    return
+        if errors or not users:
+            if not users:
+                # no users left
+                title = "Thread not created"
+            else:
+                title = None
 
-                ref = f"{user.mention} is" if creator != user else "You are"
-                embed = discord.Embed(
-                    color=self.bot.error_color,
-                    description=f"{ref} currently blocked from contacting {self.bot.user.name}.",
-                )
-                return await ctx.send(embed=embed)
+            if manual_trigger:  # not react to contact
+                embed = discord.Embed(title=title, color=self.bot.error_color, description="\n".join(errors))
+                await ctx.send(embed=embed, delete_after=10)
 
-            thread = await self.bot.threads.create(
-                recipient=user,
-                creator=creator,
-                category=category,
-                manual_trigger=manual_trigger,
-            )
-            if thread.cancelled:
+            if not users:
+                # end
                 return
 
-            if self.bot.config["dm_disabled"] in (DMDisabled.NEW_THREADS, DMDisabled.ALL_THREADS):
-                logger.info("Contacting user %s when Modmail DM is disabled.", user)
+        creator = ctx.author if manual_trigger else users[0]
 
-            if not silent and not self.bot.config.get("thread_contact_silently"):
-                if creator.id == user.id:
-                    description = self.bot.config["thread_creation_self_contact_response"]
-                else:
-                    description = self.bot.formatter.format(
-                        self.bot.config["thread_creation_contact_response"], creator=creator
-                    )
+        thread = await self.bot.threads.create(
+            recipient=users[0],
+            creator=creator,
+            category=category,
+            manual_trigger=manual_trigger,
+        )
 
-                em = discord.Embed(
-                    title=self.bot.config["thread_creation_contact_title"],
-                    description=description,
-                    color=self.bot.main_color,
+        if thread.cancelled:
+            return
+
+        if self.bot.config["dm_disabled"] in (DMDisabled.NEW_THREADS, DMDisabled.ALL_THREADS):
+            logger.info("Contacting user %s when Modmail DM is disabled.", users[0])
+
+        if not silent and not self.bot.config.get("thread_contact_silently"):
+            if creator.id == users[0].id:
+                description = self.bot.config["thread_creation_self_contact_response"]
+            else:
+                description = self.bot.formatter.format(
+                    self.bot.config["thread_creation_contact_response"], creator=creator
                 )
-                if self.bot.config["show_timestamp"]:
-                    em.timestamp = datetime.utcnow()
-                em.set_footer(text=f"{creator}", icon_url=creator.avatar_url)
-                await user.send(embed=em)
 
-            embed = discord.Embed(
-                title="Created Thread",
-                description=f"Thread started by {creator.mention} for {user.mention}.",
+            em = discord.Embed(
+                title=self.bot.config["thread_creation_contact_title"],
+                description=description,
                 color=self.bot.main_color,
             )
-            await thread.wait_until_ready()
-            await thread.channel.send(embed=embed)
+            if self.bot.config["show_timestamp"]:
+                em.timestamp = datetime.utcnow()
+            em.set_footer(text=f"{creator}", icon_url=creator.avatar_url)
+
+            for u in users:
+                await u.send(embed=em)
+
+        embed = discord.Embed(
+            title="Created Thread",
+            description=f"Thread started by {creator.mention} for {', '.join(u.mention for u in users)}.",
+            color=self.bot.main_color,
+        )
+        await thread.wait_until_ready()
+
+        if users[1:]:
+            await thread.add_users(users[1:])
+
+        await thread.channel.send(embed=embed)
 
-            if manual_trigger:
-                sent_emoji, _ = await self.bot.retrieve_emoji()
-                await self.bot.add_reaction(ctx.message, sent_emoji)
-                await asyncio.sleep(5)
+        if manual_trigger:
+            sent_emoji, _ = await self.bot.retrieve_emoji()
+            await self.bot.add_reaction(ctx.message, sent_emoji)
 
     @commands.group(invoke_without_command=True)
     @checks.has_permissions(PermissionLevel.MODERATOR)
diff --git a/cogs/utility.py b/cogs/utility.py
index bbeb8cffe0..bc813e9d6e 100644
--- a/cogs/utility.py
+++ b/cogs/utility.py
@@ -694,7 +694,7 @@ async def mention(self, ctx, *user_or_role: Union[discord.Role, discord.Member,
             option = user_or_role[0].lower()
             if option == "disable":
                 embed = discord.Embed(
-                    description=f"Disabled mention on thread creation.",
+                    description="Disabled mention on thread creation.",
                     color=self.bot.main_color,
                 )
                 self.bot.config["mention"] = None
@@ -892,7 +892,7 @@ async def config_help(self, ctx, key: str.lower = None):
                 description=f"`{key}` is an invalid key.",
             )
             if closest:
-                embed.add_field(name=f"Perhaps you meant:", value="\n".join(f"`{x}`" for x in closest))
+                embed.add_field(name="Perhaps you meant:", value="\n".join(f"`{x}`" for x in closest))
             return await ctx.send(embed=embed)
 
         config_help = self.bot.config.config_help
@@ -1861,7 +1861,7 @@ async def autotrigger_test(self, ctx, *, text):
         embed = discord.Embed(
             title="Keyword Not Found",
             color=self.bot.error_color,
-            description=f"No autotrigger keyword found.",
+            description="No autotrigger keyword found.",
         )
         return await ctx.send(embed=embed)