diff --git a/src/wormhole/db-schemas/v1.sql b/src/wormhole/db-schemas/v1.sql
index 27262ea..43785de 100644
--- a/src/wormhole/db-schemas/v1.sql
+++ b/src/wormhole/db-schemas/v1.sql
@@ -15,4 +15,11 @@ CREATE TABLE `messages`
  `message` VARCHAR,
  `when` INTEGER
 );
-CREATE INDEX `lookup` ON `messages` (`channel_id`, `side`, `msgnum`);
+CREATE INDEX `messages_idx` ON `messages` (`channel_id`, `side`, `msgnum`);
+
+CREATE TABLE `allocations`
+(
+ `channel_id` INTEGER,
+ `side` VARCHAR
+);
+CREATE INDEX `allocations_idx` ON `allocations` (`channel_id`);
diff --git a/src/wormhole/servers/relay.py b/src/wormhole/servers/relay.py
index dafba87..bedac04 100644
--- a/src/wormhole/servers/relay.py
+++ b/src/wormhole/servers/relay.py
@@ -66,8 +66,6 @@ class Channel(resource.Resource):
         self.db = db
         self.welcome = welcome
         self.expire_at = time.time() + CHANNEL_EXPIRATION_TIME
-        self.sides = set()
-        self.messages = [] # (side, msgnum, str)
         self.event_channels = set() # (side, msgnum, ep)
 
 
@@ -87,8 +85,12 @@ class Channel(resource.Resource):
         handle = (their_side, their_msgnum, ep)
         self.event_channels.add(handle)
         request.notifyFinish().addErrback(self._shutdown, handle)
-        for (msg_side, msg_msgnum, msg_str) in self.messages:
-            self.message_added(msg_side, msg_msgnum, msg_str, channels=[handle])
+        for row in self.db.execute("SELECT * FROM `messages`"
+                                   " WHERE `channel_id`=?"
+                                   " ORDER BY `when` ASC",
+                                   (self.channel_id,)).fetchall():
+            self.message_added(row["side"], row["msgnum"], row["message"],
+                               channels=[handle])
         return server.NOT_DONE_YET
 
     def _shutdown(self, _, handle):
@@ -107,12 +109,17 @@ class Channel(resource.Resource):
     def render_POST(self, request):
         # rest of URL is: SIDE/(MSGNUM|deallocate)/(post|poll)
         side = request.postpath[0]
-        self.sides.add(side)
         verb = request.postpath[1]
 
         if verb == "deallocate":
-            self.sides.remove(side)
-            if self.sides:
+            self.db.execute("DELETE FROM `allocations`"
+                            " WHERE `channel_id`=? AND `side`=?",
+                            (self.channel_id, side))
+            self.db.commit()
+            remaining = self.db.execute("SELECT COUNT(*) FROM `allocations`"
+                                        " WHERE `channel_id`=?",
+                                        (self.channel_id,)).fetchone()[0]
+            if remaining:
                 return "waiting\n"
             self.relay.free_child(self.channel_id)
             return "deleted\n"
@@ -124,13 +131,25 @@ class Channel(resource.Resource):
         msgnum = request.postpath[2]
 
         other_messages = []
-        for (msg_side, msg_msgnum, msg_str) in self.messages:
-            if msg_side != side and msg_msgnum == msgnum:
-                other_messages.append(msg_str)
+        for row in self.db.execute("SELECT `message` FROM `messages`"
+                                   " WHERE `channel_id`=? AND `side`!=?"
+                                   "       AND `msgnum`=?"
+                                   " ORDER BY `when` ASC",
+                                   (self.channel_id, side, msgnum)).fetchall():
+            other_messages.append(row["message"])
 
         if verb == "post":
             data = json.load(request.content)
-            self.messages.append( (side, msgnum, data["message"]) )
+            self.db.execute("INSERT INTO `messages`"
+                            " (`channel_id`, `side`, `msgnum`, `message`, `when`)"
+                            " VALUES (?,?,?,?,?)",
+                            (self.channel_id, side, msgnum, data["message"],
+                             time.time()))
+            self.db.execute("INSERT INTO `allocations`"
+                            " (`channel_id`, `side`)"
+                            " VALUES (?,?)",
+                            (self.channel_id, side))
+            self.db.commit()
             self.message_added(side, msgnum, data["message"])
 
         request.setHeader("content-type", "application/json; charset=utf-8")
@@ -213,6 +232,9 @@ class Relay(resource.Resource):
         return self.channels[channel_id]
 
     def free_child(self, channel_id):
+        self.db.execute("DELETE FROM `messages` WHERE `channel_id`=?",
+                        (channel_id,))
+        self.db.commit()
         self.channels.pop(channel_id)
         log.msg("freed #%d, now have %d channels" %
                 (channel_id, len(self.channels)))