diff --git a/README.md b/README.md
index 9d81e678..d367a549 100644
--- a/README.md
+++ b/README.md
@@ -47,10 +47,9 @@ Onionr ships with various application plugins ready for use out of the box:
 Currently usable:
 
 * Mail
-* Public anonymous chat
+* Public anonymous chat/message board
 * Simple webpage hosting - Will be greatly extended
 * File sharing (Work in progress)
-* Simple Message board
 
 Not yet usable:
 
diff --git a/onionr/httpapi/directconnections/__init__.py b/onionr/httpapi/directconnections/__init__.py
index 80e3b82a..b0a75f72 100644
--- a/onionr/httpapi/directconnections/__init__.py
+++ b/onionr/httpapi/directconnections/__init__.py
@@ -17,11 +17,11 @@
     You should have received a copy of the GNU General Public License
     along with this program.  If not, see <https://www.gnu.org/licenses/>.
 '''
-import threading
+import threading # For the client creation thread
 
-from flask import Response
-from flask import Blueprint
-from flask import g
+from flask import Response # For direct connection management HTTP endpoints
+from flask import Blueprint # To make the direct connection management blueprint in the webUI
+from flask import g # Mainly to access the shared toomanyobjs object
 import deadsimplekv
 
 import filepaths
@@ -49,12 +49,16 @@ class DirectConnectionManagement:
         def make_new_connection(pubkey):
             communicator = _get_communicator(g)
             resp = "pending"
+            if pubkey in communicator.shared_state.get_by_string("ServicePool").bootstrap_pending:
+                return Response(resp)
+                
             if pubkey in communicator.direct_connection_clients:
                 resp = communicator.direct_connection_clients[pubkey]
             else:
                 """Spawn a thread that will create the client and eventually add it to the
                 communicator.active_services 
                 """
-                threading.Thread(target=onionrservices.OnionrServices().create_client, args=[pubkey, communicator], daemon=True).start()
+                threading.Thread(target=onionrservices.OnionrServices().create_client, 
+                                 args=[pubkey, communicator], daemon=True).start()
 
             return Response(resp)
\ No newline at end of file
diff --git a/onionr/onionrexceptions.py b/onionr/onionrexceptions.py
index f19a4c62..b510dee8 100755
--- a/onionr/onionrexceptions.py
+++ b/onionr/onionrexceptions.py
@@ -84,6 +84,9 @@ class InvalidAddress(Exception):
 class InvalidAPIVersion(Exception):
     pass
 
+class Timeout(Exception):
+    pass
+
 # file exceptions
 
 class DiskAllocationReached(Exception):
diff --git a/onionr/onionrservices/__init__.py b/onionr/onionrservices/__init__.py
index a2a6a26a..2aefbc07 100755
--- a/onionr/onionrservices/__init__.py
+++ b/onionr/onionrservices/__init__.py
@@ -31,7 +31,6 @@ class OnionrServices:
         self.servers = {}
         self.clients = {}
         self.shutdown = False
-        return
     
     def create_server(self, peer, address, comm_inst):
         '''
@@ -55,7 +54,7 @@ class OnionrServices:
 
     @staticmethod
     def create_client(peer, comm_inst=None):
-        # Create ephemeral onion service to bootstrap connection
+        # Create ephemeral onion service to bootstrap connection to server
         if not comm_inst == None:
             try:
                 return comm_inst.direct_connection_clients[peer]
diff --git a/onionr/onionrservices/bootstrapservice.py b/onionr/onionrservices/bootstrapservice.py
index 4304cf6f..0ef8b42a 100755
--- a/onionr/onionrservices/bootstrapservice.py
+++ b/onionr/onionrservices/bootstrapservice.py
@@ -25,7 +25,16 @@ from netcontroller import get_open_port
 from . import httpheaders
 from onionrutils import stringvalidators, epoch
 import config, onionrblocks, filepaths
+import onionrexceptions
 import deadsimplekv as simplekv
+import warden
+from . import pool
+
+def __bootstrap_timeout(server: WSGIServer, timeout: int, signal_object):
+    time.sleep(timeout)
+    signal_object.timed_out = True
+    server.stop()
+
 def bootstrap_client_service(peer, comm_inst=None, bootstrap_timeout=300):
     '''
         Bootstrap client services
@@ -33,9 +42,17 @@ def bootstrap_client_service(peer, comm_inst=None, bootstrap_timeout=300):
     
     if not stringvalidators.validate_pub_key(peer):
         raise ValueError('Peer must be valid base32 ed25519 public key')
+    
+    connection_pool = None
+
+    # here we use a lambda for the timeout thread to set to true
+    timed_out = lambda: None
+    timed_out.timed_out = False
 
     bootstrap_port = get_open_port()
     bootstrap_app = Flask(__name__)
+    bootstrap_app.config['MAX_CONTENT_LENGTH'] = 1 * 1024
+
     http_server = WSGIServer(('127.0.0.1', bootstrap_port), bootstrap_app, log=None)
     try:
         assert comm_inst is not None
@@ -43,6 +60,7 @@ def bootstrap_client_service(peer, comm_inst=None, bootstrap_timeout=300):
         pass
     else:
         comm_inst.service_greenlets.append(http_server)
+        connection_pool = comm_inst.shared_state.get(pool.ServicePool)
     
     bootstrap_address = ''
     shutdown = False
@@ -71,12 +89,16 @@ def bootstrap_client_service(peer, comm_inst=None, bootstrap_timeout=300):
             return Response("")
 
     with Controller.from_port(port=config.get('tor.controlPort')) as controller:
+        connection_pool.bootstrap_pending.append(peer)
         # Connect to the Tor process for Onionr
         controller.authenticate(config.get('tor.controlpassword'))
         # Create the v3 onion service
         response = controller.create_ephemeral_hidden_service({80: bootstrap_port}, key_type = 'NEW', key_content = 'ED25519-V3', await_publication = True)
         onionrblocks.insert(response.service_id, header='con', sign=True, encryptType='asym', 
         asymPeer=peer, disableForward=True, expire=(epoch.get_epoch() + bootstrap_timeout))
+        
+        threading.Thread(target=__bootstrap_timeout, args=[http_server, bootstrap_timeout], daemon=True)
+
         # Run the bootstrap server
         try:
             http_server.serve_forever()
@@ -86,5 +108,10 @@ def bootstrap_client_service(peer, comm_inst=None, bootstrap_timeout=300):
     # Add the address to the client pool
     if not comm_inst is None:
         comm_inst.direct_connection_clients[peer] = response.service_id
+    
+    connection_pool.bootstrap_pending.remove(peer)
+
+    if timed_out.timed_out:
+        raise onionrexceptions.Timeout
     # Now that the bootstrap server has received a server, return the address
     return key_store.get(bs_id)
diff --git a/onionr/onionrservices/pool.py b/onionr/onionrservices/pool.py
new file mode 100644
index 00000000..4f26029c
--- /dev/null
+++ b/onionr/onionrservices/pool.py
@@ -0,0 +1,29 @@
+'''
+    Onionr - Private P2P Communication
+
+    Holds active onionrservices clients and servers
+'''
+'''
+    This program is free software: you can redistribute it and/or modify
+    it under the terms of the GNU General Public License as published by
+    the Free Software Foundation, either version 3 of the License, or
+    (at your option) any later version.
+
+    This program is distributed in the hope that it will be useful,
+    but WITHOUT ANY WARRANTY; without even the implied warranty of
+    MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+    GNU General Public License for more details.
+
+    You should have received a copy of the GNU General Public License
+    along with this program.  If not, see <https://www.gnu.org/licenses/>.
+'''
+from onionrutils import epoch
+class ServicePool:
+    def __init__(self):
+        self.servers = []
+        self.clients = []
+        self.bootstrap_pending = []
+    
+    def add_server(self, service):
+        self.servers.append((service, epoch.get_epoch()))
+        
\ No newline at end of file
diff --git a/onionr/onionrservices/warden/__init__.py b/onionr/onionrservices/warden/__init__.py
new file mode 100644
index 00000000..7173f75c
--- /dev/null
+++ b/onionr/onionrservices/warden/__init__.py
@@ -0,0 +1,3 @@
+from . import client # Client connection warden. Monitors & validates connection security.
+from . import server # Server connection warden. Monitors and validates server security
+from . import watchdog # Watchdog. Oversees running services for statistic collection and TTL control
diff --git a/onionr/onionrservices/warden/bootstrap.py b/onionr/onionrservices/warden/bootstrap.py
new file mode 100644
index 00000000..bd37e0a7
--- /dev/null
+++ b/onionr/onionrservices/warden/bootstrap.py
@@ -0,0 +1,19 @@
+'''
+    Onionr - Private P2P Communication
+
+    Bootstrap warden monitors the bootstrap server
+'''
+'''
+    This program is free software: you can redistribute it and/or modify
+    it under the terms of the GNU General Public License as published by
+    the Free Software Foundation, either version 3 of the License, or
+    (at your option) any later version.
+
+    This program is distributed in the hope that it will be useful,
+    but WITHOUT ANY WARRANTY; without even the implied warranty of
+    MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+    GNU General Public License for more details.
+
+    You should have received a copy of the GNU General Public License
+    along with this program.  If not, see <https://www.gnu.org/licenses/>.
+'''
diff --git a/onionr/onionrservices/warden/client.py b/onionr/onionrservices/warden/client.py
new file mode 100644
index 00000000..e69de29b
diff --git a/onionr/onionrservices/warden/server.py b/onionr/onionrservices/warden/server.py
new file mode 100644
index 00000000..e69de29b