diff --git a/jinja2/utils.py b/jinja2/utils.py

index 49e9e9a..0e67d88 100644

--- a/jinja2/utils.py

+++ b/jinja2/utils.py

@@ -11,6 +11,8 @@

 import re

 import sys

 import errno

+from string import ascii_letters as _letters

+from string import digits as _digits

 try:

     from thread import allocate_lock

 except ImportError:

@@ -19,19 +21,6 @@ from collections import deque

 from itertools import imap

-_word_split_re = re.compile(r'(\s+)')

-_punctuation_re = re.compile(

-    '^(?P<lead>(?:%s)*)(?P<middle>.*?)(?P<trail>(?:%s)*)$' % (

-        '|'.join(imap(re.escape, ('(', '<', '<'))),

-        '|'.join(imap(re.escape, ('.', ',', ')', '>', '\n', '>')))

-    )

-)

-_simple_email_re = re.compile(r'^\S+@[a-zA-Z0-9._-]+\.[a-zA-Z0-9._-]+$')

-_striptags_re = re.compile(r'(|<[^>]*>)')

-_entity_re = re.compile(r'&([^;]+);')

-_letters = 'abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ'

-_digits = '0123456789'

-

 # special singleton representing missing values for the runtime

 missing = type('MissingType', (), {'__repr__': lambda x: 'missing'})()

@@ -271,32 +260,61 @@ def urlize(text, trim_url_limit=None, nofollow=False):

     trim_url = lambda x, limit=trim_url_limit: limit is not None \

                          and (x[:limit] + (len(x) >=limit and '...'

                          or '')) or x

-    words = _word_split_re.split(unicode(escape(text)))

+    words = re.split(r"(\s+)", unicode(escape(text)))

     nofollow_attr = nofollow and ' rel="nofollow"' or ''

     for i, word in enumerate(words):

-        match = _punctuation_re.match(word)

+        head, middle, tail = "", word, ""

+        match = re.match(r"^([(<]|<)+", middle)

+

         if match:

-            lead, middle, trail = match.groups()

-            if middle.startswith('www.') or (

-                '@' not in middle and

-                not middle.startswith('http://') and

-                len(middle) > 0 and

-                middle[0] in _letters + _digits and (

-                    middle.endswith('.org') or

-                    middle.endswith('.net') or

-                    middle.endswith('.com')

-                )):

-                middle = '%s' % (middle,

-                    nofollow_attr, trim_url(middle))

-            if middle.startswith('http://') or \

-               middle.startswith('https://'):

-                middle = '%s' % (middle,

-                    nofollow_attr, trim_url(middle))

-            if '@' in middle and not middle.startswith('www.') and \

-               not ':' in middle and _simple_email_re.match(middle):

-                middle = '%s' % (middle, middle)

-            if lead + middle + trail != word:

-                words[i] = lead + middle + trail

+            head = match.group()

+            middle = middle[match.end() :]

+

+        # Unlike lead, which is anchored to the start of the string,

+        # need to check that the string ends with any of the characters

+        # before trying to match all of them, to avoid backtracking.

+        if middle.endswith((")", ">", ".", ",", "\n", ">")):

+            match = re.search(r"([)>.,\n]|>)+$", middle)

+

+            if match:

+                tail = match.group()

+                middle = middle[: match.start()]

+

+        if middle.startswith("www.") or (

+            "@" not in middle

+            and not middle.startswith("http://")

+            and not middle.startswith("https://")

+            and len(middle) > 0

+            and middle[0] in _letters + _digits

+            and (

+                middle.endswith(".org")

+                or middle.endswith(".net")

+                or middle.endswith(".com")

+            )

+        ):

+            middle = '%s' % (

+                middle,

+                nofollow_attr,

+                trim_url(middle),

+            )

+

+        if middle.startswith("http://") or middle.startswith("https://"):

+            middle = '%s' % (

+                middle,

+                nofollow_attr,

+                trim_url(middle),

+            )

+

+        if (

+            "@" in middle

+            and not middle.startswith("www.")

+            and ":" not in middle

+            and re.match(r"^\S@\w[\w.-]*\.\w$", middle)

+        ):

+            middle = '%s' % (middle, middle)

+

+        words[i] = head + middle + tail

+

     return u''.join(words)