diff --git a/chatcommands.py b/chatcommands.py
index c118c719ad..9288f9f0ff 100644
--- a/chatcommands.py
+++ b/chatcommands.py
@@ -4,6 +4,7 @@
     tell_rooms, tell_rooms_with, get_message
 # noinspection PyUnresolvedReferences
 from globalvars import GlobalVars
+exit_mode = GlobalVars.exit_mode
 import findspam
 # noinspection PyUnresolvedReferences
 from datetime import datetime
@@ -26,7 +27,7 @@
 from ast import literal_eval
 # noinspection PyCompatibility
 import regex
-from helpers import exit_mode, only_blacklists_changed, only_modules_changed, log, expand_shorthand_link, \
+from helpers import only_blacklists_changed, only_modules_changed, log, expand_shorthand_link, \
     reload_modules, chunk_list
 from classes import Post
 from classes.feedback import *
diff --git a/chatcommunicate.py b/chatcommunicate.py
index bdc1b4f06c..ae035e91bf 100644
--- a/chatcommunicate.py
+++ b/chatcommunicate.py
@@ -63,6 +63,39 @@ class CmdException(Exception):
 _pickle_run = threading.Event()
 
 
+# Ignore flake8 warning as this class is intended to be private.
+class _cleanup:  # noqa: N801
+    """ Utilities for cleaning up """
+    _counter = 0
+    _cv = threading.Condition(lock=threading.Lock())
+    terminate = threading.Event()
+    cleanup_finished = threading.Event()
+
+    @staticmethod
+    def t_started():
+        """ Indicate a new thread is started. """
+        with _cleanup._cv:
+            _cleanup._counter += 1
+
+    @staticmethod
+    def t_stopped():
+        """ Indicate a thread terminated. """
+        with _cleanup._cv:
+            if _cleanup._counter > 0:
+                _cleanup._counter -= 1
+            else:
+                raise ValueError("More threads terminated than started.")
+            _cleanup._cv.notify()
+
+    @staticmethod
+    def wait_t_terminate():
+        _cleanup.terminate.set()
+        with _cleanup._cv:
+            while _cleanup._counter != 0:
+                _cleanup._cv.wait()
+        return
+
+
 def init(username, password, try_cookies=True):
     global _clients
     global _rooms
@@ -119,13 +152,35 @@ def init(username, password, try_cookies=True):
             except EOFError:
                 pass
 
+    if os.path.isfile("messageQueue.p"):
+        # Restore previous session, if exists
+        with open("messageQueue.p", "rb") as queue_file:
+            try:
+                _msg_queue = pickle.load(queue_file)
+            except EOFError:
+                pass
+
+    # Tell GlobalVars that this process needs cleaning up.
+    with GlobalVars.need_cleanup_list_lock:
+        GlobalVars.need_cleanup.append(_cleanup.cleanup_finished)
+
     threading.Thread(name="pickle ---rick--- runner", target=pickle_last_messages, daemon=True).start()
     threading.Thread(name="message sender", target=send_messages, daemon=True).start()
+    threading.Thread(name="exit watcher", target=exit_watcher, daemon=True).start()
 
     if try_cookies:
         datahandling.dump_cookies()
 
 
+def exit_watcher():
+    """ Watch for the program termination event and dump current session at exit. """
+    GlobalVars.terminate.wait()
+    _cleanup.wait_t_terminate()
+    with open("messageQueue.p", "wb") as pickle_file:
+        pickle.dump(_msg_queue, pickle_file)
+    _cleanup.cleanup_finished.set()
+
+
 def join_command_rooms():
     for site, roomid in _command_rooms:
         room = _clients[site].get_room(roomid)
@@ -199,16 +254,20 @@ def add_room(room, roles):
 
 
 def pickle_last_messages():
-    while True:
+    _cleanup.t_started()
+    while not _cleanup.terminate.isSet():
         _pickle_run.wait()
         _pickle_run.clear()
 
         with open("messageData.p", "wb") as pickle_file:
             pickle.dump(_last_messages, pickle_file)
 
+    _cleanup.t_stopped()
+
 
 def send_messages():
-    while True:
+    _cleanup.t_started()
+    while not _cleanup.terminate.isSet():
         room, msg, report_data = _msg_queue.get()
         if len(msg) > 500 and "\n" not in msg:
             log('warn', 'Discarded the following message because it was over 500 characters')
@@ -255,6 +314,8 @@ def send_messages():
 
         _msg_queue.task_done()
 
+    _cleanup.t_stopped()
+
 
 def on_msg(msg, client):
     global _room_roles
@@ -323,6 +384,9 @@ def tell_rooms_without(prop, msg, notify_site="", report_data=None):
 def tell_rooms(msg, has, hasnt, notify_site="", report_data=None):
     global _rooms
 
+    if _cleanup.terminate.isSet():
+        return  # To prevent writing to _msg_queue while dumping
+
     msg = msg.rstrip()
     target_rooms = set()
 
diff --git a/excepthook.py b/excepthook.py
index 32f410dd2f..c5424b9f8c 100644
--- a/excepthook.py
+++ b/excepthook.py
@@ -7,8 +7,9 @@
 # noinspection PyPackageRequirements
 from websocket import WebSocketConnectionClosedException
 import requests
-from helpers import exit_mode, log, log_exception
+from helpers import log, log_exception
 from globalvars import GlobalVars
+exit_mode = GlobalVars.exit_mode
 
 
 # noinspection PyProtectedMember
diff --git a/globalvars.py b/globalvars.py
index 7ac49d451f..36c47a7f7d 100644
--- a/globalvars.py
+++ b/globalvars.py
@@ -19,6 +19,8 @@
 else:
     from sh.contrib import git
 
+from helpers import exit_mode
+
 
 CommitInfo = namedtuple('CommitInfo', ['id', 'id_full', 'author', 'message'])
 
@@ -180,6 +182,23 @@ class GlobalVars:
 
     valid_content = """This is a totally valid post that should never be caught. Any blacklist or watchlist item that triggers on this item should be avoided. java.io.BbbCccDddException: nothing wrong found. class Safe { perfect valid code(int float &#%$*v a b c =+ /* - 0 1 2 3 456789.EFGQ} English 中文Français Español Português Italiano Deustch ~@#%*-_/'()?!:;" vvv kkk www sss ttt mmm absolute std::adjacent_find (power).each do |s| bbb end ert zal l gsopsq kdowhs@ xjwk* %_sooqmzb xjwpqpxnf.  Please don't blacklist disk-partition.com, it's a valid domain (though it also gets spammed rather frequently)."""  # noqa: E501
 
+    # Any thread that need cleaning up before the program exits shall add an threading.Event()
+    # object to the following queue, and prior to all modification the lock must be acquired.
+    need_cleanup = []
+    need_cleanup_list_lock = threading.Lock()
+    # This event is set when the program is about to exit. Those need clean up shall be actively
+    # monitoring this event.
+    terminate = threading.Event()
+
+    @staticmethod
+    def exit_mode(*args, code=0):
+        GlobalVars.terminate.set()
+        with GlobalVars.need_cleanup_list_lock:
+            for item in GlobalVars.need_cleanup:
+                # Wait for every thread needing clean up to finish.
+                item.wait()
+            exit_mode(args, GlobalVars.standby_mode, code)
+
     @staticmethod
     def reload():
         GlobalVars.commit = commit = git_commit_info()
diff --git a/helpers.py b/helpers.py
index 70d82e5898..6cbf23425d 100644
--- a/helpers.py
+++ b/helpers.py
@@ -18,12 +18,11 @@
 import sqlite3
 
 
-def exit_mode(*args, code=0):
+def exit_mode(*args, standby_mode, code=0):
     args = set(args)
 
     if not (args & {'standby', 'no_standby'}):
-        from globalvars import GlobalVars
-        standby = 'standby' if GlobalVars.standby_mode else 'no_standby'
+        standby = 'standby' if standby_mode else 'no_standby'
         args.add(standby)
 
     with open("exit.txt", "w", encoding="utf-8") as f:
diff --git a/metasmoke.py b/metasmoke.py
index 80799226ae..f4fdc5a62f 100644
--- a/metasmoke.py
+++ b/metasmoke.py
@@ -3,6 +3,7 @@
 import requests
 import importlib  # for .reload()
 from globalvars import GlobalVars
+exit_mode = GlobalVars.exit_mode
 import threading
 # noinspection PyPackageRequirements
 import websocket
@@ -24,7 +25,7 @@
 import spamhandling
 import classes
 import chatcommunicate
-from helpers import log, exit_mode, only_blacklists_changed, \
+from helpers import log, only_blacklists_changed, \
     only_modules_changed, blacklist_integrity_check, reload_modules
 from gitmanager import GitManager
 import findspam
diff --git a/test/test_chatcommunicate.py b/test/test_chatcommunicate.py
index c5d634d262..e7706eb414 100644
--- a/test/test_chatcommunicate.py
+++ b/test/test_chatcommunicate.py
@@ -114,7 +114,7 @@ def test_init(room_config, client_constructor, thread):
     client_constructor.assert_any_call("stackoverflow.com")
     client_constructor.assert_any_call("meta.stackexchange.com")
 
-    assert thread.call_count == 2
+    assert thread.call_count == 3
     thread.assert_any_call(name="pickle ---rick--- runner", target=chatcommunicate.pickle_last_messages, daemon=True)
     thread.assert_any_call(name="message sender", target=chatcommunicate.send_messages, daemon=True)
 
@@ -145,7 +145,7 @@ def throw_every_other(*_):
     client_constructor.assert_any_call("stackoverflow.com")
     client_constructor.assert_any_call("meta.stackexchange.com")
 
-    assert thread.call_count == 2
+    assert thread.call_count == 3
     thread.assert_any_call(name="pickle ---rick--- runner", target=chatcommunicate.pickle_last_messages, daemon=True)
     thread.assert_any_call(name="message sender", target=chatcommunicate.send_messages, daemon=True)
 
diff --git a/ws.py b/ws.py
index 20729f3043..fbe26080b4 100755
--- a/ws.py
+++ b/ws.py
@@ -24,6 +24,7 @@
 from datetime import datetime
 from spamhandling import check_if_spam_json
 from globalvars import GlobalVars
+exit_mode = GlobalVars.exit_mode
 from datahandling import _load_pickle, PICKLE_STORAGE, load_files, filter_auto_ignored_posts
 from metasmoke import Metasmoke
 from metasmoke_cache import MetasmokeCache
@@ -33,7 +34,7 @@
 import requests
 # noinspection PyPackageRequirements
 from tld.utils import update_tld_names, TldIOError
-from helpers import exit_mode, log, Helpers, log_exception
+from helpers import log, Helpers, log_exception
 from flovis import Flovis
 from tasks import Tasks