diff --git a/src/conf_mode/dns_dynamic.py b/src/conf_mode/dns_dynamic.py
index 809c650d9..99fa8feee 100755
--- a/src/conf_mode/dns_dynamic.py
+++ b/src/conf_mode/dns_dynamic.py
@@ -1,177 +1,187 @@
 #!/usr/bin/env python3
 #
 # Copyright (C) 2018-2023 VyOS maintainers and contributors
 #
 # This program is free software; you can redistribute it and/or modify
 # it under the terms of the GNU General Public License version 2 or later as
 # published by the Free Software Foundation.
 #
 # This program is distributed in the hope that it will be useful,
 # but WITHOUT ANY WARRANTY; without even the implied warranty of
 # MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
 # GNU General Public License for more details.
 #
 # You should have received a copy of the GNU General Public License
 # along with this program.  If not, see <http://www.gnu.org/licenses/>.
 
 import os
-
+import re
 from sys import exit
 
 from vyos.base import Warning
 from vyos.config import Config
 from vyos.configverify import verify_interface_exists
 from vyos.template import render
 from vyos.utils.process import call
 from vyos import ConfigError
 from vyos import airbag
 airbag.enable()
 
 config_file = r'/run/ddclient/ddclient.conf'
 systemd_override = r'/run/systemd/system/ddclient.service.d/override.conf'
 
 # Dynamic interfaces that might not exist when the configuration is loaded
 dynamic_interfaces = ('pppoe', 'sstpc')
 
 # Protocols that require zone
 zone_necessary = ['cloudflare', 'digitalocean', 'godaddy', 'hetzner', 'gandi',
                   'nfsn', 'nsupdate']
 zone_supported = zone_necessary + ['dnsexit2', 'zoneedit1']
 
 # Protocols that do not require username
 username_unnecessary = ['1984', 'cloudflare', 'cloudns', 'digitalocean', 'dnsexit2',
                         'duckdns', 'freemyip', 'hetzner', 'keysystems', 'njalla',
                         'nsupdate', 'regfishde']
 
 # Protocols that support TTL
 ttl_supported = ['cloudflare', 'dnsexit2', 'gandi', 'hetzner', 'godaddy', 'nfsn',
                  'nsupdate']
 
 # Protocols that support both IPv4 and IPv6
 dualstack_supported = ['cloudflare', 'digitalocean', 'dnsexit2', 'duckdns',
                        'dyndns2', 'easydns', 'freedns', 'hetzner', 'infomaniak',
                        'njalla']
 
 # dyndns2 protocol in ddclient honors dual stack for selective servers
 # because of the way it is implemented in ddclient
 dyndns_dualstack_servers = ['members.dyndns.org', 'dynv6.com']
 
 def get_config(config=None):
     if config:
         conf = config
     else:
         conf = Config()
 
     base = ['service', 'dns', 'dynamic']
     if not conf.exists(base):
         return None
 
     dyndns = conf.get_config_dict(base, key_mangling=('-', '_'),
                                   no_tag_node_value_mangle=True,
                                   get_first_key=True,
                                   with_recursive_defaults=True)
 
     dyndns['config_file'] = config_file
     return dyndns
 
 def verify(dyndns):
     # bail out early - looks like removal from running config
     if not dyndns or 'name' not in dyndns:
         return None
 
     # Dynamic DNS service provider - configuration validation
     for service, config in dyndns['name'].items():
 
         error_msg_req = f'is required for Dynamic DNS service "{service}"'
         error_msg_uns = f'is not supported for Dynamic DNS service "{service}"'
 
         for field in ['protocol', 'address', 'host_name']:
             if field not in config:
                 raise ConfigError(f'"{field.replace("_", "-")}" {error_msg_req}')
 
         # If dyndns address is an interface, ensure
         # that the interface exists (or just warn if dynamic interface)
         # and that web-options are not set
         if config['address'] != 'web':
             # exclude check interface for dynamic interfaces
             if config['address'].startswith(dynamic_interfaces):
                 Warning(f'Interface "{config["address"]}" does not exist yet and cannot '
                         f'be used for Dynamic DNS service "{service}" until it is up!')
             else:
                 verify_interface_exists(config['address'])
             if 'web_options' in config:
                 raise ConfigError(f'"web-options" is applicable only when using HTTP(S) '
                                   f'web request to obtain the IP address')
 
+        # Warn if using checkip.dyndns.org, as it does not support HTTPS
+        # See: https://github.com/ddclient/ddclient/issues/597
+        if 'web_options' in config:
+            if 'url' not in config['web_options']:
+                raise ConfigError(f'"url" in "web-options" {error_msg_req} '
+                                  f'with protocol "{config["protocol"]}"')
+            elif re.search("^(https?://)?checkip\.dyndns\.org", config['web_options']['url']):
+                Warning(f'"checkip.dyndns.org" does not support HTTPS requests for IP address '
+                        f'lookup. Please use a different IP address lookup service.')
+
         # RFC2136 uses 'key' instead of 'password'
         if config['protocol'] != 'nsupdate' and 'password' not in config:
             raise ConfigError(f'"password" {error_msg_req}')
 
         # Other RFC2136 specific configuration validation
         if config['protocol'] == 'nsupdate':
             if 'password' in config:
                 raise ConfigError(f'"password" {error_msg_uns} with protocol "{config["protocol"]}"')
             for field in ['server', 'key']:
                 if field not in config:
                     raise ConfigError(f'"{field}" {error_msg_req} with protocol "{config["protocol"]}"')
 
         if config['protocol'] in zone_necessary and 'zone' not in config:
             raise ConfigError(f'"zone" {error_msg_req} with protocol "{config["protocol"]}"')
 
         if config['protocol'] not in zone_supported and 'zone' in config:
             raise ConfigError(f'"zone" {error_msg_uns} with protocol "{config["protocol"]}"')
 
         if config['protocol'] not in username_unnecessary and 'username' not in config:
             raise ConfigError(f'"username" {error_msg_req} with protocol "{config["protocol"]}"')
 
         if config['protocol'] not in ttl_supported and 'ttl' in config:
             raise ConfigError(f'"ttl" {error_msg_uns} with protocol "{config["protocol"]}"')
 
         if config['ip_version'] == 'both':
             if config['protocol'] not in dualstack_supported:
                 raise ConfigError(f'Both IPv4 and IPv6 at the same time {error_msg_uns} '
                                   f'with protocol "{config["protocol"]}"')
             # dyndns2 protocol in ddclient honors dual stack only for dyn.com (dyndns.org)
             if config['protocol'] == 'dyndns2' and 'server' in config and config['server'] not in dyndns_dualstack_servers:
                 raise ConfigError(f'Both IPv4 and IPv6 at the same time {error_msg_uns} '
                                   f'for "{config["server"]}" with protocol "{config["protocol"]}"')
 
         if {'wait_time', 'expiry_time'} <= config.keys() and int(config['expiry_time']) < int(config['wait_time']):
                 raise ConfigError(f'"expiry-time" must be greater than "wait-time" for '
                                   f'Dynamic DNS service "{service}"')
 
     return None
 
 def generate(dyndns):
     # bail out early - looks like removal from running config
     if not dyndns or 'name' not in dyndns:
         return None
 
     render(config_file, 'dns-dynamic/ddclient.conf.j2', dyndns, permission=0o600)
     render(systemd_override, 'dns-dynamic/override.conf.j2', dyndns)
     return None
 
 def apply(dyndns):
     systemd_service = 'ddclient.service'
     # Reload systemd manager configuration
     call('systemctl daemon-reload')
 
     # bail out early - looks like removal from running config
     if not dyndns or 'name' not in dyndns:
         call(f'systemctl stop {systemd_service}')
         if os.path.exists(config_file):
             os.unlink(config_file)
     else:
         call(f'systemctl reload-or-restart {systemd_service}')
 
     return None
 
 if __name__ == '__main__':
     try:
         c = get_config()
         verify(c)
         generate(c)
         apply(c)
     except ConfigError as e:
         print(e)
         exit(1)