diff --git a/Doc/library/ssl.rst b/Doc/library/ssl.rst
index 9b3bdd5489d..45bb65ff071 100644
--- a/Doc/library/ssl.rst
+++ b/Doc/library/ssl.rst
@@ -429,6 +429,10 @@ Certificate handling
       Matching of IP addresses, when present in the subjectAltName field
       of the certificate, is now supported.
 
+   .. versionchanged:: 3.7
+      Allow wildcard when it is the leftmost and the only character
+      in that segment.
+
 .. function:: cert_time_to_seconds(cert_time)
 
    Return the time in seconds since the Epoch, given the ``cert_time``
diff --git a/Lib/ssl.py b/Lib/ssl.py
index 75caae0c440..fa83606e7cd 100644
--- a/Lib/ssl.py
+++ b/Lib/ssl.py
@@ -221,7 +221,7 @@ class CertificateError(ValueError):
     pass
 
 
-def _dnsname_match(dn, hostname, max_wildcards=1):
+def _dnsname_match(dn, hostname):
     """Matching according to RFC 6125, section 6.4.3
 
     http://tools.ietf.org/html/rfc6125#section-6.4.3
@@ -233,7 +233,12 @@ def _dnsname_match(dn, hostname, max_wildcards=1):
     leftmost, *remainder = dn.split(r'.')
 
     wildcards = leftmost.count('*')
-    if wildcards > max_wildcards:
+    if wildcards == 1 and len(leftmost) > 1:
+        # Only match wildcard in leftmost segment.
+        raise CertificateError(
+            "wildcard can only be present in the leftmost segment: " + repr(dn))
+
+    if wildcards > 1:
         # Issue #17980: avoid denials of service by refusing more
         # than one wildcard per fragment.  A survey of established
         # policy among SSL implementations showed it to be a
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index aa2429ac982..c65290b945f 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -512,10 +512,11 @@ class BasicSocketTests(unittest.TestCase):
         fail(cert, 'Xa.com')
         fail(cert, '.a.com')
 
-        # only match one left-most wildcard
+        # only match wildcards when they are the only thing
+        # in left-most segment
         cert = {'subject': ((('commonName', 'f*.com'),),)}
-        ok(cert, 'foo.com')
-        ok(cert, 'f.com')
+        fail(cert, 'foo.com')
+        fail(cert, 'f.com')
         fail(cert, 'bar.com')
         fail(cert, 'foo.a.com')
         fail(cert, 'bar.foo.com')
@@ -552,8 +553,8 @@ class BasicSocketTests(unittest.TestCase):
         # are supported.
         idna = 'www*.pythön.org'.encode("idna").decode("ascii")
         cert = {'subject': ((('commonName', idna),),)}
-        ok(cert, 'www.pythön.org'.encode("idna").decode("ascii"))
-        ok(cert, 'www1.pythön.org'.encode("idna").decode("ascii"))
+        fail(cert, 'www.pythön.org'.encode("idna").decode("ascii"))
+        fail(cert, 'www1.pythön.org'.encode("idna").decode("ascii"))
         fail(cert, 'ftp.pythön.org'.encode("idna").decode("ascii"))
         fail(cert, 'pythön.org'.encode("idna").decode("ascii"))
 
@@ -637,7 +638,7 @@ class BasicSocketTests(unittest.TestCase):
         # Issue #17980: avoid denials of service by refusing more than one
         # wildcard per fragment.
         cert = {'subject': ((('commonName', 'a*b.com'),),)}
-        ok(cert, 'axxb.com')
+        fail(cert, 'axxb.com')
         cert = {'subject': ((('commonName', 'a*b.co*'),),)}
         fail(cert, 'axxb.com')
         cert = {'subject': ((('commonName', 'a*b*.com'),),)}
diff --git a/Misc/ACKS b/Misc/ACKS
index fc7154f762e..54d8d62b633 100644
--- a/Misc/ACKS
+++ b/Misc/ACKS
@@ -1467,6 +1467,7 @@ Nathan Paul Simons
 Guilherme Simões
 Adam Simpkins
 Ravi Sinha
+Mandeep Singh
 Janne Sinkkonen
 Ng Pheng Siong
 Yann Sionneau
diff --git a/Misc/NEWS.d/next/Library/2017-11-26-17-00-52.bpo-23033.YGXRWT.rst b/Misc/NEWS.d/next/Library/2017-11-26-17-00-52.bpo-23033.YGXRWT.rst
new file mode 100644
index 00000000000..cecc10aebb9
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2017-11-26-17-00-52.bpo-23033.YGXRWT.rst
@@ -0,0 +1,3 @@
+Wildcard is now supported in hostname when it is one and only character in
+the left most segment of hostname in second argument of
+:meth:`ssl.match_hostname`.  Patch by Mandeep Singh.