diff --git a/NEWS b/NEWS
index cd3c31efd7..2a3ebe6c11 100644
--- a/NEWS
+++ b/NEWS
@@ -2,6 +2,23 @@ This file is used to auto-generate the "Changelog" section of Sopel's website.
 When adding new entries, follow the style guide in NEWS.spec.md to avoid causing
 problems with the site build.
 
+Changes between 6.6.4 and 6.6.5
+===============================
+
+Module changes
+--------------
+
+* Fixed url module not cleaning punctuation when auto-titling [[#1515][]]
+* Fixed url module's punctuation-cleaning on Python 2 [[#1517][]]
+* Fixed `.redditor` command with newer `praw` versions (4.0+) [[#1506][]]
+* Reloading modules now runs their `shutdown()` routines [[#1412][]]
+
+  [#1412]: https://github.com/sopel-irc/sopel/pull/1412
+  [#1506]: https://github.com/sopel-irc/sopel/pull/1506
+  [#1515]: https://github.com/sopel-irc/sopel/pull/1515
+  [#1517]: https://github.com/sopel-irc/sopel/pull/1517
+
+
 Changes between 6.6.3 and 6.6.4
 ===============================
 
diff --git a/sopel/__init__.py b/sopel/__init__.py
index 5e9213fee7..8cf89be400 100644
--- a/sopel/__init__.py
+++ b/sopel/__init__.py
@@ -26,7 +26,7 @@
 from collections import namedtuple
 import re
 
-__version__ = '6.6.4'
+__version__ = '6.6.5'
 
 
 def _version_info(version=__version__):
diff --git a/sopel/bot.py b/sopel/bot.py
index 8b6e41a71a..7e0fefc866 100644
--- a/sopel/bot.py
+++ b/sopel/bot.py
@@ -578,6 +578,8 @@ def _shutdown(self):
                         shutdown_method.__module__, e
                     )
                 )
+        # Avoid calling shutdown methods if we already have.
+        self.shutdown_methods = []
 
     def cap_req(self, module_name, capability, arg=None, failure_callback=None,
                 success_callback=None):
diff --git a/sopel/modules/reddit.py b/sopel/modules/reddit.py
index e6ab1d9fa0..263f7c215b 100644
--- a/sopel/modules/reddit.py
+++ b/sopel/modules/reddit.py
@@ -119,8 +119,10 @@ def redditor_info(bot, trigger, match=None):
         client_secret=None,
     )
     match = match or trigger
-    try:
+    try:  # praw <4.0 style
         u = r.get_redditor(match.group(2))
+    except AttributeError:  # praw >=4.0 style
+        u = r.redditor(match.group(2))
     except Exception:  # TODO: Be specific
         if commanded:
             bot.say('No such Redditor.')
diff --git a/sopel/modules/reload.py b/sopel/modules/reload.py
index 87c428ada8..9b4592880a 100644
--- a/sopel/modules/reload.py
+++ b/sopel/modules/reload.py
@@ -11,7 +11,7 @@
 import collections
 import sys
 import time
-from sopel.tools import iteritems
+from sopel.tools import stderr, iteritems
 import sopel.loader
 import sopel.module
 import subprocess
@@ -65,6 +65,22 @@ def reload_module_tree(bot, name, seen=None, silent=False):
     old_callables = {}
     for obj_name, obj in iteritems(vars(old_module)):
         if callable(obj):
+            if (getattr(obj, '__name__', None) == 'shutdown' and
+                        obj in bot.shutdown_methods):
+                # If this is a shutdown method, call it first.
+                try:
+                    stderr(
+                        "calling %s.%s" % (
+                            obj.__module__, obj.__name__,
+                        )
+                    )
+                    obj(bot)
+                except Exception as e:
+                    stderr(
+                        "Error calling shutdown method for module %s:%s" % (
+                            obj.__module__, e
+                        )
+                    )
             bot.unregister(obj)
         elif (type(obj) is ModuleType and
               obj.__name__.startswith(name + '.') and
diff --git a/sopel/modules/url.py b/sopel/modules/url.py
index be7ce04fa4..fc45a75b29 100644
--- a/sopel/modules/url.py
+++ b/sopel/modules/url.py
@@ -100,7 +100,7 @@ def trim_url(url):
 
             # clean unmatched parentheses/braces/brackets
             for (opener, closer) in [('(', ')'), ('[', ']'), ('{', '}'), ('<', '>')]:
-                if url[-1] is closer and url.count(opener) < url.count(closer):
+                if (url[-1] == closer) and (url.count(opener) < url.count(closer)):
                     url = url[:-1]
 
             return url
@@ -167,7 +167,7 @@ def title_auto(bot, trigger):
         if bot.memory['safety_cache'][trigger]['positives'] > 1:
             return
 
-    urls = find_urls(trigger)
+    urls = find_urls(trigger, clean=True)
     if len(urls) == 0:
         return