diff --git a/docs/cog_guides/core.rst b/docs/cog_guides/core.rst
index 69e1895494f..71bc5113dc8 100644
--- a/docs/cog_guides/core.rst
+++ b/docs/cog_guides/core.rst
@@ -1475,9 +1475,6 @@ helpset maxpages
 
 Set the maximum number of help pages sent in a server channel.
 
-.. Note:: This setting does not apply to menu help.
-
-
 If a help message contains more pages than this value, the help message will
 be sent to the command author via DM. This is to help reduce spam in server
 text channels.
@@ -4378,4 +4375,4 @@ uptime
 
 **Description**
 
-Shows Red's uptime.
\ No newline at end of file
+Shows Red's uptime.
diff --git a/redbot/core/commands/help.py b/redbot/core/commands/help.py
index dcff3f0410e..66920780d59 100644
--- a/redbot/core/commands/help.py
+++ b/redbot/core/commands/help.py
@@ -856,23 +856,36 @@ async def send_pages(
         if help_settings.use_menus.value >= HelpMenuSetting.buttons.value:
             use_select = help_settings.use_menus.value == 3
             select_only = help_settings.use_menus.value == 4
-            await SimpleMenu(
+            menu = SimpleMenu(
                 pages,
                 timeout=help_settings.react_timeout,
                 use_select_menu=use_select,
                 use_select_only=select_only,
-            ).start(ctx)
+            )
+            # Send menu to DMs if max pages is 0
+            if help_settings.max_pages_in_guild == 0:
+                await menu.start_dm(ctx.author)
+            else:
+                await menu.start(ctx)
 
         elif (
             can_user_react_in(ctx.me, ctx.channel)
             and help_settings.use_menus is HelpMenuSetting.reactions
         ):
+            use_DMs = help_settings.max_pages_in_guild == 0
+            destination = ctx.author if use_DMs else ctx.channel
             # Specifically ensuring the menu's message is sent prior to returning
-            m = await (ctx.send(embed=pages[0]) if embed else ctx.send(pages[0]))
+            m = await (destination.send(embed=pages[0]) if embed else destination.send(pages[0]))
             c = menus.DEFAULT_CONTROLS if len(pages) > 1 else {"\N{CROSS MARK}": menus.close_menu}
             # Allow other things to happen during menu timeout/interaction.
+            if use_DMs:
+                menu_ctx = await ctx.bot.get_context(m)
+                # Monkeypatch so help listens for reactions from the original author, not the bot
+                menu_ctx.author = ctx.author
+            else:
+                menu_ctx = ctx
             asyncio.create_task(
-                menus.menu(ctx, pages, c, message=m, timeout=help_settings.react_timeout)
+                menus.menu(menu_ctx, pages, c, message=m, timeout=help_settings.react_timeout)
             )
             # menu needs reactions added manually since we fed it a message
             menus.start_adding_reactions(m, c.keys())
diff --git a/redbot/core/core_commands.py b/redbot/core/core_commands.py
index 944e9ff059e..1b780b1ff7d 100644
--- a/redbot/core/core_commands.py
+++ b/redbot/core/core_commands.py
@@ -4446,8 +4446,6 @@ async def helpset_pagecharlimt(self, ctx: commands.Context, limit: int):
     async def helpset_maxpages(self, ctx: commands.Context, pages: int):
         """Set the maximum number of help pages sent in a server channel.
 
-        Note: This setting does not apply to menu help.
-
         If a help message contains more pages than this value, the help message will
         be sent to the command author via DM. This is to help reduce spam in server
         text channels.