diff --git a/cogs/pin.py b/cogs/pin.py
index 4f169e4..61e6e6f 100644
--- a/cogs/pin.py
+++ b/cogs/pin.py
@@ -1,7 +1,11 @@
 import config
 from discord.ext.commands import Cog
 from discord.enums import MessageType
-
+from discord import Embed
+import aiohttp
+import gidgethub.aiohttp
+from helpers.checks import check_if_collaborator
+from helpers.checks import check_if_pin_channel
 
 class Pin(Cog):
     """
@@ -11,16 +15,37 @@ class Pin(Cog):
     def __init__(self, bot):
         self.bot = bot
 
+    async def get_pinboard(self, gh, channel):
+        # Find pinboard pin
+        pinboard_msg = None
+        for msg in reversed(await channel.pins()):
+            if msg.author == self.bot.user and len(msg.embeds) > 0 and msg.embeds[0].title == "Pinboard":
+                # Found pinboard, return content and gist id
+                id = msg.embeds[0].url.split("/")[-1]
+                data = await gh.getitem(f"/gists/{id}")
+                return (id, data["files"]["pinboard.md"]["content"])
+
+        # Create pinboard pin if it does not exist
+        data = await gh.post("/gists", data={"files": {"pinboard.md": {"content": "Old pins are available here:\n\n"}}, "description": f"Pinboard for SwitchRoot #{channel.name}", "public": True})
+        msg = await channel.send(embed=Embed(title="Pinboard", description="Old pins are moved to the pinboard to make space for new ones. Check it out!", url=data["html_url"]))
+        await msg.pin()
+        return (data["id"], data["files"]["pinboard.md"]["content"])
+
+    async def add_pin_to_pinboard(self, channel, data):
+        if config.github_oauth_token == "":
+            # Don't add to gist pinboard if we don't have an oauth token
+            return
+
+        async with aiohttp.ClientSession() as session:
+            gh = gidgethub.aiohttp.GitHubAPI(session, "RoboCop-NG", oauth_token=config.github_oauth_token)
+            (id, content) = await self.get_pinboard(gh, channel)
+            content += "- " + data + "\n"
+
+            await gh.patch(f"/gists/{id}", data={"files": {"pinboard.md": {"content": content}}})
+
     # Use raw_reaction to allow pinning old messages.
     @Cog.listener()
     async def on_raw_reaction_add(self, payload):
-        # TODO: handle more than 50 pinned message
-        # BODY: If there are more than 50 pinned messages,
-        # BODY: we should move the oldest pin to a pinboard
-        # BODY: channel to make room for the new pin.
-        # BODY: This is why we use the pin reaction to remember
-        # BODY: that a message is pinned.
-
         # Check that the user wants to pin this message
         if payload.emoji.name not in ["📌", "📍"]:
             return
@@ -45,17 +70,24 @@ class Pin(Cog):
                     if reaction.emoji == "📌":
                         if reaction.me:
                             return
-                        break
+                        else:
+                            break
 
-                # Wait for the automated "Pinned" message so we can delete it
-                waitable = self.bot.wait_for('message', check=check)
+                # Add pin to pinboard, create one if none is found
+                await self.add_pin_to_pinboard(target_chan, target_msg.jump_url)
 
-                # Pin the message
-                await target_msg.pin()
+                # Avoid staying "stuck" waiting for the pin message if message
+                # was already manually pinned
+                if not target_msg.pinned:
+                    # Wait for the automated "Pinned" message so we can delete it
+                    waitable = self.bot.wait_for('message', check=check)
 
-                # Delete the automated Pinned message
-                msg = await waitable
-                await msg.delete()
+                    # Pin the message
+                    await target_msg.pin()
+
+                    # Delete the automated Pinned message
+                    msg = await waitable
+                    await msg.delete()
 
                 # Add a Pin reaction so we remember that the message is pinned
                 await target_msg.add_reaction("📌")
diff --git a/config_template.py b/config_template.py
index 9c69127..46caaba 100644
--- a/config_template.py
+++ b/config_template.py
@@ -94,3 +94,6 @@ spy_channels = general_channels
 # Channels and roles where users can pin messages
 allowed_pin_channels = []
 allowed_pin_roles = []
+
+# Used for the pinboard. Leave empty if you don't wish for a gist pinboard.
+github_oauth_token = ""
diff --git a/requirements.txt b/requirements.txt
index de97058..1a0200c 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -3,4 +3,6 @@ git+https://github.com/Rapptz/discord.py@rewrite
 asyncio
 python-dateutil
 humanize
-parsedatetime
\ No newline at end of file
+parsedatetime
+aiohttp
+gidgethub