diff --git a/CHANGES.md b/CHANGES.md
index 75888e5b..f191b955 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -2,6 +2,7 @@
 
 * Update html5lib 1.1 (f87487a) to 1.2-dev (3e500bb)
 * Update package resource API 63.2.0 (3ae44cd) to 67.3.2 (b9bf2ec)
+* Update urllib3 1.26.13 (25fbd5f) to 1.26.14 (a06c05c)
 * Change remove calls to legacy py2 fix encoding function
 * Change requirements for pure py3
 * Change codebase cleanups
diff --git a/lib/urllib3/_version.py b/lib/urllib3/_version.py
index 308d7f28..7c031661 100644
--- a/lib/urllib3/_version.py
+++ b/lib/urllib3/_version.py
@@ -1,2 +1,2 @@
 # This file is protected via CODEOWNERS
-__version__ = "1.26.13"
+__version__ = "1.26.14"
diff --git a/lib/urllib3/connection.py b/lib/urllib3/connection.py
index 10fb36c4..54b96b19 100644
--- a/lib/urllib3/connection.py
+++ b/lib/urllib3/connection.py
@@ -229,6 +229,11 @@ class HTTPConnection(_HTTPConnection, object):
             )
 
     def request(self, method, url, body=None, headers=None):
+        # Update the inner socket's timeout value to send the request.
+        # This only triggers if the connection is re-used.
+        if getattr(self, "sock", None) is not None:
+            self.sock.settimeout(self.timeout)
+
         if headers is None:
             headers = {}
         else:
diff --git a/lib/urllib3/connectionpool.py b/lib/urllib3/connectionpool.py
index 70873927..c23d736b 100644
--- a/lib/urllib3/connectionpool.py
+++ b/lib/urllib3/connectionpool.py
@@ -379,7 +379,7 @@ class HTTPConnectionPool(ConnectionPool, RequestMethods):
 
         timeout_obj = self._get_timeout(timeout)
         timeout_obj.start_connect()
-        conn.timeout = timeout_obj.connect_timeout
+        conn.timeout = Timeout.resolve_default_timeout(timeout_obj.connect_timeout)
 
         # Trigger any extra validation we need to do.
         try:
diff --git a/lib/urllib3/util/timeout.py b/lib/urllib3/util/timeout.py
index ff69593b..78e18a62 100644
--- a/lib/urllib3/util/timeout.py
+++ b/lib/urllib3/util/timeout.py
@@ -2,9 +2,8 @@ from __future__ import absolute_import
 
 import time
 
-# The default socket timeout, used by httplib to indicate that no timeout was
-# specified by the user
-from socket import _GLOBAL_DEFAULT_TIMEOUT
+# The default socket timeout, used by httplib to indicate that no timeout was; specified by the user
+from socket import _GLOBAL_DEFAULT_TIMEOUT, getdefaulttimeout
 
 from ..exceptions import TimeoutStateError
 
@@ -116,6 +115,10 @@ class Timeout(object):
     # __str__ provided for backwards compatibility
     __str__ = __repr__
 
+    @classmethod
+    def resolve_default_timeout(cls, timeout):
+        return getdefaulttimeout() if timeout is cls.DEFAULT_TIMEOUT else timeout
+
     @classmethod
     def _validate_timeout(cls, value, name):
         """Check that a timeout attribute is valid.
diff --git a/lib/urllib3/util/url.py b/lib/urllib3/util/url.py
index 3a169a43..e5682d3b 100644
--- a/lib/urllib3/util/url.py
+++ b/lib/urllib3/util/url.py
@@ -50,7 +50,7 @@ _variations = [
     "(?:(?:%(hex)s:){0,6}%(hex)s)?::",
 ]
 
-UNRESERVED_PAT = r"ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789._!\-~"
+UNRESERVED_PAT = r"ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789._\-~"
 IPV6_PAT = "(?:" + "|".join([x % _subs for x in _variations]) + ")"
 ZONE_ID_PAT = "(?:%25|%)(?:[" + UNRESERVED_PAT + "]|%[a-fA-F0-9]{2})+"
 IPV6_ADDRZ_PAT = r"\[" + IPV6_PAT + r"(?:" + ZONE_ID_PAT + r")?\]"
@@ -303,7 +303,7 @@ def _normalize_host(host, scheme):
 
 
 def _idna_encode(name):
-    if name and any([ord(x) > 128 for x in name]):
+    if name and any(ord(x) >= 128 for x in name):
         try:
             import idna
         except ImportError: