diff --git a/django/utils/html.py b/django/utils/html.py
index a0ad5f3d00..207620ed86 100644
--- a/django/utils/html.py
+++ b/django/utils/html.py
@@ -23,6 +23,8 @@ word_split_re = re.compile(r'(\s+)')
 punctuation_re = re.compile('^(?P<lead>(?:%s)*)(?P<middle>.*?)(?P<trail>(?:%s)*)$' % \
     ('|'.join([re.escape(x) for x in LEADING_PUNCTUATION]),
     '|'.join([re.escape(x) for x in TRAILING_PUNCTUATION])))
+simple_url_re = re.compile(r'^https?://\w')
+simple_url_2_re = re.compile(r'^www\.|^(?!http)\w[^@]+\.(com|net|org)$')
 simple_email_re = re.compile(r'^\S+@\S+\.\S+$')
 link_target_attribute_re = re.compile(r'(<a [^>]*?)target=[^\s>]+')
 html_gunk_re = re.compile(r'(?:<br clear="all">|<i><\/i>|<b><\/b>|<em><\/em>|<strong><\/strong>|<\/?smallcaps>|<\/?uppercase>)', re.IGNORECASE)
@@ -150,11 +152,9 @@ def urlize(text, trim_url_limit=None, nofollow=False, autoescape=False):
             # Make URL we want to point to.
             url = None
             nofollow_attr = ' rel="nofollow"' if nofollow else ''
-            if middle.startswith('http://') or middle.startswith('https://'):
+            if simple_url_re.match(middle):
                 url = smart_urlquote(middle)
-            elif middle.startswith('www.') or ('@' not in middle and \
-                    middle and middle[0] in string.ascii_letters + string.digits and \
-                    (middle.endswith('.org') or middle.endswith('.net') or middle.endswith('.com'))):
+            elif simple_url_2_re.match(middle):
                 url = smart_urlquote('http://%s' % middle)
             elif not ':' in middle and simple_email_re.match(middle):
                 local, domain = middle.rsplit('@', 1)
diff --git a/tests/regressiontests/defaultfilters/tests.py b/tests/regressiontests/defaultfilters/tests.py
index 2c7cdb17a6..2f3d012346 100644
--- a/tests/regressiontests/defaultfilters/tests.py
+++ b/tests/regressiontests/defaultfilters/tests.py
@@ -268,6 +268,14 @@ class DefaultFiltersTests(TestCase):
         self.assertEqual(urlize('info@c✶.org'),
             u'<a href="mailto:info@xn--c-lgq.org">info@c✶.org</a>')
 
+        # Check urlize doesn't highlight malformed URIs - see #16395
+        self.assertEqual(urlize('http:///www.google.com'),
+           u'http:///www.google.com')
+        self.assertEqual(urlize('http://.google.com'),
+            u'http://.google.com')
+        self.assertEqual(urlize('http://@foo.com'),
+            u'http://@foo.com')
+
     def test_wordcount(self):
         self.assertEqual(wordcount(''), 0)
         self.assertEqual(wordcount(u'oneword'), 1)