diff --git a/changelogs/fragments/urls-cidr-no-proxy.yml b/changelogs/fragments/urls-cidr-no-proxy.yml
new file mode 100644
index 00000000000000..dfe11c8f6b63a4
--- /dev/null
+++ b/changelogs/fragments/urls-cidr-no-proxy.yml
@@ -0,0 +1,2 @@
+minor_changes:
+- urls.py - Support CIDR ranges for no_proxy
diff --git a/lib/ansible/module_utils/urls.py b/lib/ansible/module_utils/urls.py
index c4c8e3ab7dfaed..1e61cfe57bbb93 100644
--- a/lib/ansible/module_utils/urls.py
+++ b/lib/ansible/module_utils/urls.py
@@ -37,6 +37,7 @@
 import email.policy
 import email.utils
 import http.client
+import ipaddress
 import mimetypes
 import netrc
 import os
@@ -67,6 +68,7 @@
 from ansible.module_utils.basic import missing_required_lib
 from ansible.module_utils.common.collections import Mapping, is_sequence
 from ansible.module_utils.common.text.converters import to_bytes, to_native, to_text
+from ansible.module_utils.common import warnings
 
 try:
     import ssl
@@ -300,6 +302,49 @@ def http_open(self, req):
         return self.do_open(UnixHTTPConnection(self._unix_socket), req)
 
 
+class ProxyHandler(urllib.request.ProxyHandler):
+    _SPLITPORT_RE = re.compile('(.*):([0-9]{1,5})', re.DOTALL)
+
+    @classmethod
+    def _splitport(cls, host):
+        # Derived from cpython urllib.parse
+        port = None
+        if (match := cls._SPLITPORT_RE.fullmatch(host)):
+            host, port = match.groups()
+        return host, port or None
+
+    @staticmethod
+    def _matches(host, port, bypass_network, bypass_port, scheme):
+        if not port:
+            port = '443' if scheme == 'https' else '80'
+        if bypass_port and port != bypass_port:
+            return False
+        return host in bypass_network
+
+    def proxy_open(self, req, *args):
+        """Implements proxy bypassing for cidr ranges"""
+        hostonly, port = self._splitport(req.host)
+        try:
+            req_ip = ipaddress.ip_address(hostonly)
+        except ValueError:
+            return super().proxy_open(req, *args)
+
+        no_proxy = self.proxies.get('no') or ''
+        for bypass in map(str.strip, no_proxy.split(',')):
+            if '/' not in bypass:
+                continue
+            bypass_host, bypass_port = self._splitport(bypass)
+            try:
+                bypass_network = ipaddress.ip_network(bypass_host)
+            except ValueError as e:
+                warnings.warn(f'no_proxy entry appears to be a CIDR range, but could not be parsed: {e}')
+                continue
+            if self._matches(req_ip, port, bypass_network, bypass_port, req.type):
+                return None
+
+        return super().proxy_open(req, *args)
+
+
 class ParseResultDottedDict(dict):
     '''
     A dict that acts similarly to the ParseResult named tuple from urllib
@@ -844,9 +889,10 @@ def open(self, method, url, data=None, headers=None, use_proxy=None,
         headers.update(auth_headers)
         handlers.extend(auth_handlers)
 
+        proxies = None
         if not use_proxy:
-            proxyhandler = urllib.request.ProxyHandler({})
-            handlers.append(proxyhandler)
+            proxies = {}
+        handlers.append(ProxyHandler(proxies))
 
         if not context:
             context = make_context(
diff --git a/test/integration/targets/setup_proxy/files/hamsandwich.py b/test/integration/targets/setup_proxy/files/hamsandwich.py
new file mode 100644
index 00000000000000..d3c487b34cefc8
--- /dev/null
+++ b/test/integration/targets/setup_proxy/files/hamsandwich.py
@@ -0,0 +1,32 @@
+from __future__ import annotations
+
+from proxy.http.proxy import HttpProxyBasePlugin
+from proxy.http.parser import HttpParser, httpParserStates
+
+
+class HamSandwichPlugin(HttpProxyBasePlugin):
+
+    def __init__(self, *args, **kwargs):
+        super().__init__(*args, **kwargs)
+        self.parser = None
+        self.parsable = True
+
+    def handle_upstream_chunk(self, chunk):
+        if not self.parsable:
+            return chunk
+
+        if not self.parser:
+            self.parser = HttpParser.response(chunk)
+        else:
+            self.parser.parse(chunk)
+
+        if self.parser.state == httpParserStates.INITIALIZED:
+            # This is likely TLS without interception
+            self.parsable = False
+            return chunk
+
+        if not self.parser.is_complete:
+            return None
+
+        self.parser.add_header(b'X-Sandwich', b'ham')
+        return memoryview(bytearray(self.parser.build_response()))
diff --git a/test/integration/targets/setup_proxy/handlers/main.yml b/test/integration/targets/setup_proxy/handlers/main.yml
new file mode 100644
index 00000000000000..4e1e28e53244c4
--- /dev/null
+++ b/test/integration/targets/setup_proxy/handlers/main.yml
@@ -0,0 +1,2 @@
+- name: stop proxy.py
+  command: kill {{ proxy_py_pid }}
diff --git a/test/integration/targets/setup_proxy/meta/main.yml b/test/integration/targets/setup_proxy/meta/main.yml
new file mode 100644
index 00000000000000..1810d4bec988cb
--- /dev/null
+++ b/test/integration/targets/setup_proxy/meta/main.yml
@@ -0,0 +1,2 @@
+dependencies:
+  - setup_remote_tmp_dir
diff --git a/test/integration/targets/setup_proxy/tasks/main.yml b/test/integration/targets/setup_proxy/tasks/main.yml
new file mode 100644
index 00000000000000..7fbba38aaae665
--- /dev/null
+++ b/test/integration/targets/setup_proxy/tasks/main.yml
@@ -0,0 +1,43 @@
+- name: install proxy.py
+  pip:
+    name: proxy.py
+    virtualenv: '{{ remote_tmp_dir }}/proxy_py'
+    virtualenv_command: "{{ ansible_python_interpreter }} -m venv"
+  notify: stop proxy.py
+
+- name: get venv site-packages
+  command: >-
+    {{ remote_tmp_dir }}/proxy_py/bin/python -c 'import site; print(site.getsitepackages()[0])'
+  register: proxy_py_site_packages
+
+- name: install proxy.py plugin
+  copy:
+    src: hamsandwich.py
+    dest: '{{ proxy_py_site_packages.stdout }}/hamsandwich.py'
+
+- name: start proxy.py
+  command: >-
+    {{ remote_tmp_dir }}/proxy_py/bin/proxy --port 8080 --log-file "{{ remote_tmp_dir }}/proxy_py/proxy_py.log"
+    --plugins hamsandwich.HamSandwichPlugin --pid-file "{{ remote_tmp_dir }}/proxy_py/proxy_py.pid"
+  async: 120
+  poll: 0
+  register: proxy_py
+
+- name: wait for proxy.py to start
+  wait_for:
+    port: 8080
+    connect_timeout: 1
+    timeout: 10
+
+- name: get proxy.py pid
+  slurp:
+    path: '{{ remote_tmp_dir }}/proxy_py/proxy_py.pid'
+  register: proxy_py_slurp_pid
+
+- name: set fact for proxy.py pid
+  set_fact:
+    proxy_py_pid: '{{ proxy_py_slurp_pid.content|b64decode }}'
+
+- name: set fact for proxy host
+  set_fact:
+    http_proxy: 'http://127.0.0.1:8080'
diff --git a/test/integration/targets/uri/aliases b/test/integration/targets/uri/aliases
index 90ef161f598809..202ee5fc4a616c 100644
--- a/test/integration/targets/uri/aliases
+++ b/test/integration/targets/uri/aliases
@@ -1,3 +1,4 @@
 destructive
 shippable/posix/group1
 needs/httptester
+needs/target/setup_proxy
diff --git a/test/integration/targets/uri/tasks/main.yml b/test/integration/targets/uri/tasks/main.yml
index a818107d99ca46..1d4f37a0a109cd 100644
--- a/test/integration/targets/uri/tasks/main.yml
+++ b/test/integration/targets/uri/tasks/main.yml
@@ -727,6 +727,9 @@
 - name: Test unix socket
   import_tasks: install-socat-and-test-unix-socket.yml
 
+- name: Test proxy
+  import_tasks: proxy.yml
+
 - name: ensure skip action
   uri:
     url: http://example.com
diff --git a/test/integration/targets/uri/tasks/proxy.yml b/test/integration/targets/uri/tasks/proxy.yml
new file mode 100644
index 00000000000000..d92c4582165a40
--- /dev/null
+++ b/test/integration/targets/uri/tasks/proxy.yml
@@ -0,0 +1,117 @@
+- include_role:
+    name: setup_proxy
+
+- name: Get IP address for ansible.http.tests
+  command: >-
+    {{ ansible_python_interpreter }} -c 'import socket; print(socket.gethostbyname("{{ httpbin_host }}"))'
+  register: httpbin_ip
+
+- name: Test http over http proxy
+  uri:
+    url: http://{{ httpbin_host }}/get
+  environment:
+    http_proxy: '{{ http_proxy }}'
+  register: http_over_http
+  failed_when: http_over_http.x_sandwich is undefined
+
+- name: Test https over http proxy
+  uri:
+    url: https://{{ httpbin_host }}/get
+  environment:
+    https_proxy: '{{ http_proxy }}'
+  register: https_over_http
+  # failed_when:
+  # failure checking is handled by the assert at the bottom comparing logs
+  # because we aren't running a proxy that can inspect the https stream
+  # there won't be added headers
+
+- name: Test request without a proxy
+  uri:
+    url: http://{{ httpbin_host }}/get
+  register: request_without_proxy
+  failed_when: request_without_proxy.x_sandwich is defined
+
+- name: Test request with proxy and no_proxy=hostname
+  uri:
+    url: http://{{ httpbin_host }}/get
+  environment:
+    http_proxy: '{{ http_proxy }}'
+    no_proxy: '{{ httpbin_host }}'
+  register: no_proxy_hostname
+  failed_when: no_proxy_hostname.x_sandwich is defined
+
+- name: Test request with proxy and no_proxy=ip
+  uri:
+    url: http://{{ httpbin_ip.stdout }}/get
+  environment:
+    http_proxy: '{{ http_proxy }}'
+    no_proxy: '{{ httpbin_ip.stdout }}'
+  register: no_proxy_ip
+  failed_when: no_proxy_ip.x_sandwich is defined
+
+- name: Test request with proxy and no_proxy=cidr/32
+  uri:
+    url: http://{{ httpbin_ip.stdout }}/get
+  environment:
+    http_proxy: '{{ http_proxy }}'
+    no_proxy: '{{ httpbin_ip.stdout }}/32'
+  register: no_proxy_cidr_32
+  failed_when: no_proxy_cidr_32.x_sandwich is defined
+
+- name: Test request with proxy and no_proxy=cidr/24
+  uri:
+    url: http://{{ httpbin_ip.stdout }}/get
+  environment:
+    http_proxy: '{{ http_proxy }}'
+    no_proxy: '{{ httpbin_cidr }}'
+  register: no_proxy_cidr_24
+  vars:
+    httpbin_cidr: "{{ httpbin_ip.stdout.split('.')[:3]|join('.') }}.0/24"
+  failed_when: no_proxy_cidr_24.x_sandwich is defined
+
+- name: Test request with proxy and non-matching no_proxy=cidr
+  uri:
+    url: http://{{ httpbin_ip.stdout }}/get
+  environment:
+    http_proxy: '{{ http_proxy }}'
+    no_proxy: 1.2.3.0/24
+  register: no_proxy_non_matching_cidr
+  failed_when: no_proxy_non_matching_cidr.x_sandwich is undefined
+
+- name: Test request with proxy and no_proxy=cidr:port
+  uri:
+    url: http://{{ httpbin_ip.stdout }}/get
+  environment:
+    http_proxy: '{{ http_proxy }}'
+    no_proxy: '{{ httpbin_ip.stdout }}/32:80'
+  register: no_proxy_cidr_port
+  failed_when: no_proxy_cidr_port.x_sandwich is defined
+
+- name: Test request with proxy and non-matching no_proxy=cidr:port
+  uri:
+    url: http://{{ httpbin_ip.stdout }}/get
+  environment:
+    http_proxy: '{{ http_proxy }}'
+    no_proxy: '{{ httpbin_ip.stdout }}/32:8080'
+  register: no_proxy_non_matching_cidr_port
+  failed_when: no_proxy_non_matching_cidr_port.x_sandwich is undefined
+
+- slurp:
+    path: "{{ remote_tmp_dir }}/proxy_py/proxy_py.log"
+  register: proxy_py_logs
+
+- debug:
+    msg: '{{ proxy_py_logs.content|b64decode }}'
+
+- assert:
+    that:
+      - >-
+        log_content is contains "CONNECT " ~ httpbin_host ~ ":443"
+      # https over http
+      - >-
+        log_content|regex_findall("CONNECT ")|length == 1
+      # 3 http over http
+      - >-
+        log_content|regex_findall('GET')|length == 3
+  vars:
+    log_content: '{{ proxy_py_logs.content|b64decode }}'