diff --git a/freeipa.spec.in b/freeipa.spec.in
index 9165c7764e2..623731c5cc1 100755
--- a/freeipa.spec.in
+++ b/freeipa.spec.in
@@ -324,6 +324,11 @@ BuildRequires:  libunistring-devel
 # 0.13.0-2: fix for missing dependency on python-six
 BuildRequires:  python3-lesscpy >= 0.13.0-2
 BuildRequires:  cracklib-dicts
+%if 0%{?rhel}
+BuildRequires: python3-urllib3 >= 1.24.2-3
+%else
+BuildRequires: python3-urllib3 >= 1.25.8
+%endif
 # ONLY_CLIENT
 %endif
 
@@ -569,7 +574,7 @@ Requires: rpm-libs
 %if 0%{?rhel}
 Requires: python3-urllib3 >= 1.24.2-3
 %else
-Requires: python3-urllib3 >= 1.25.7
+Requires: python3-urllib3 >= 1.25.8
 %endif
 
 %description -n python3-ipaserver
diff --git a/ipalib/x509.py b/ipalib/x509.py
index 5adb511d8b0..0b65d347639 100644
--- a/ipalib/x509.py
+++ b/ipalib/x509.py
@@ -36,7 +36,6 @@
 import datetime
 import enum
 import ipaddress
-import ssl
 import base64
 import re
 
@@ -53,6 +52,11 @@
 from pyasn1_modules import rfc2315, rfc2459
 import six
 
+try:
+    from urllib3.util import ssl_match_hostname
+except ImportError:
+    from urllib3.packages import ssl_match_hostname
+
 from ipalib import errors
 from ipapython.dnsutil import DNSName
 
@@ -385,6 +389,7 @@ def san_a_label_dns_names(self):
         return result
 
     def match_hostname(self, hostname):
+        # The caller is expected to catch any exceptions
         match_cert = {}
 
         match_cert['subject'] = match_subject = []
@@ -401,8 +406,7 @@ def match_hostname(self, hostname):
             for value in values:
                 match_san.append(('DNS', value))
 
-        # deprecated in Python3.7 without replacement
-        ssl.match_hostname(  # pylint: disable=deprecated-method
+        ssl_match_hostname.match_hostname(
             match_cert, DNSName(hostname).ToASCII()
         )
 
diff --git a/ipaserver/install/cainstance.py b/ipaserver/install/cainstance.py
index fa8942d2ad8..cd7b6902447 100644
--- a/ipaserver/install/cainstance.py
+++ b/ipaserver/install/cainstance.py
@@ -30,7 +30,6 @@
 import os
 import re
 import shutil
-import ssl
 import sys
 import syslog
 import time
@@ -2378,7 +2377,7 @@ def check_ipa_ca_san(cert):
 
     try:
         cert.match_hostname(expect)
-    except ssl.CertificateError:
+    except x509.ssl_match_hostname.CertificateError:
         raise errors.ValidationError(
             name='certificate',
             error='Does not have a \'{}\' SAN'.format(expect)
diff --git a/ipaserver/install/server/upgrade.py b/ipaserver/install/server/upgrade.py
index 8f3d5735360..d208379d01d 100644
--- a/ipaserver/install/server/upgrade.py
+++ b/ipaserver/install/server/upgrade.py
@@ -12,7 +12,6 @@
 import glob
 import shutil
 import fileinput
-import ssl
 import stat
 import sys
 import tempfile
@@ -717,7 +716,7 @@ def http_certificate_ensure_ipa_ca_dnsname(http):
 
     try:
         cert.match_hostname(expect)
-    except ssl.CertificateError:
+    except x509.ssl_match_hostname.CertificateError:
         if certs.is_ipa_issued_cert(api, cert):
             request_id = certmonger.get_request_id(
                 {'cert-file': paths.HTTPD_CERT_FILE})