diff --git a/CHANGES.rst b/CHANGES.rst
index b2b8ae6..0150d85 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -1,6 +1,9 @@
 Changes
 =======
 
+* Accept ``iPAddress`` subject alternative name fields in TLS certificates.
+  (Issue #258)
+
 1.10.2 (2015-02-25)
 +++++++++++++++++++
 
diff --git a/dummyserver/certs/server.ip_san.crt b/dummyserver/certs/server.ip_san.crt
new file mode 100644
index 000000000..58689d64d
--- /dev/null
+++ b/dummyserver/certs/server.ip_san.crt
@@ -0,0 +1,21 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/dummyserver/server.py b/dummyserver/server.py
index 18d81e1..3190835 100755
--- a/dummyserver/server.py
+++ b/dummyserver/server.py
@@ -32,6 +32,10 @@ NO_SAN_CERTS = {
     'certfile': os.path.join(CERTS_PATH, 'server.no_san.crt'),
     'keyfile': DEFAULT_CERTS['keyfile']
 }
+IP_SAN_CERTS = {
+    'certfile': os.path.join(CERTS_PATH, 'server.ip_san.crt'),
+    'keyfile': DEFAULT_CERTS['keyfile']
+}
 DEFAULT_CA = os.path.join(CERTS_PATH, 'cacert.pem')
 DEFAULT_CA_BAD = os.path.join(CERTS_PATH, 'client_bad.pem')
 NO_SAN_CA = os.path.join(CERTS_PATH, 'cacert.no_san.pem')
diff --git a/urllib3/packages/ssl_match_hostname/__init__.py b/urllib3/packages/ssl_match_hostname/__init__.py
index dd59a75fd..d6594eb26 100644
--- a/urllib3/packages/ssl_match_hostname/__init__.py
+++ b/urllib3/packages/ssl_match_hostname/__init__.py
@@ -1,5 +1,11 @@
+import sys
+
 try:
-    # Python 3.2+
+    # Our match_hostname function is the same as 3.5's, so we only want to
+    # import the match_hostname function if it's at least that good.
+    if sys.version_info < (3, 5):
+        raise ImportError("Fallback to vendored code")
+
     from ssl import CertificateError, match_hostname
 except ImportError:
     try:
diff --git a/urllib3/packages/ssl_match_hostname/_implementation.py b/urllib3/packages/ssl_match_hostname/_implementation.py
index 52f428733..1fd42f38a 100644
--- a/urllib3/packages/ssl_match_hostname/_implementation.py
+++ b/urllib3/packages/ssl_match_hostname/_implementation.py
@@ -4,8 +4,20 @@
 # stdlib.   http://docs.python.org/3/license.html
 
 import re
+import sys
+
+# ipaddress has been backported to 2.6+ in pypi.  If it is installed on the
+# system, use it to handle IPAddress ServerAltnames (this was added in
+# python-3.5) otherwise only do DNS matching.  This allows
+# backports.ssl_match_hostname to continue to be used all the way back to
+# python-2.4.
+try:
+    import ipaddress
+except ImportError:
+    ipaddress = None
+
+__version__ = '3.5.0.1'
 
-__version__ = '3.4.0.2'
 
 class CertificateError(ValueError):
     pass
@@ -64,6 +76,23 @@ def _dnsname_match(dn, hostname, max_wildcards=1):
     return pat.match(hostname)
 
 
+def _to_unicode(obj):
+    if isinstance(obj, str) and sys.version_info < (3,):
+        obj = unicode(obj, encoding='ascii', errors='strict')
+    return obj
+
+def _ipaddress_match(ipname, host_ip):
+    """Exact matching of IP addresses.
+
+    RFC 6125 explicitly doesn't define an algorithm for this
+    (section 1.7.2 - "Out of Scope").
+    """
+    # OpenSSL may add a trailing newline to a subjectAltName's IP address
+    # Divergence from upstream: ipaddress can't handle byte str
+    ip = ipaddress.ip_address(_to_unicode(ipname).rstrip())
+    return ip == host_ip
+
+
 def match_hostname(cert, hostname):
     """Verify that *cert* (in decoded format as returned by
     SSLSocket.getpeercert()) matches the *hostname*.  RFC 2818 and RFC 6125
@@ -73,12 +102,35 @@ def match_hostname(cert, hostname):
     returns nothing.
     """
     if not cert:
-        raise ValueError("empty or no certificate")
+        raise ValueError("empty or no certificate, match_hostname needs a "
+                         "SSL socket or SSL context with either "
+                         "CERT_OPTIONAL or CERT_REQUIRED")
+    try:
+        # Divergence from upstream: ipaddress can't handle byte str
+        host_ip = ipaddress.ip_address(_to_unicode(hostname))
+    except ValueError:
+        # Not an IP address (common case)
+        host_ip = None
+    except UnicodeError:
+        # Divergence from upstream: Have to deal with ipaddress not taking
+        # byte strings.  addresses should be all ascii, so we consider it not
+        # an ipaddress in this case
+        host_ip = None
+    except AttributeError:
+        # Divergence from upstream: Make ipaddress library optional
+        if ipaddress is None:
+            host_ip = None
+        else:
+            raise
     dnsnames = []
     san = cert.get('subjectAltName', ())
     for key, value in san:
         if key == 'DNS':
-            if _dnsname_match(value, hostname):
+            if host_ip is None and _dnsname_match(value, hostname):
+                return
+            dnsnames.append(value)
+        elif key == 'IP Address':
+            if host_ip is not None and _ipaddress_match(value, host_ip):
                 return
             dnsnames.append(value)
     if not dnsnames: