diff --git a/CHANGES/6002.misc b/CHANGES/6002.misc
new file mode 100644
index 00000000000..5df927cf65d
--- /dev/null
+++ b/CHANGES/6002.misc
@@ -0,0 +1,2 @@
+Implemented end-to-end testing of sending HTTP and HTTPS requests
+via ``proxy.py``.
diff --git a/requirements/dev.txt b/requirements/dev.txt
index 59ca566d7fe..9364ad351e6 100644
--- a/requirements/dev.txt
+++ b/requirements/dev.txt
@@ -163,6 +163,8 @@ pluggy==0.13.1
     #   pytest
 pre-commit==2.15.0
     # via -r requirements/lint.txt
+proxy.py==2.3.1
+    # via -r requirements/test.txt
 py==1.10.0
     # via
     #   -r requirements/lint.txt
@@ -277,6 +279,7 @@ typing-extensions==3.7.4.3
     #   -r requirements/lint.txt
     #   async-timeout
     #   mypy
+    #   proxy.py
 uritemplate==3.0.1
     # via gidgethub
 urllib3==1.26.5
diff --git a/requirements/test.txt b/requirements/test.txt
index 8ba2b11d792..d5c4f2d271c 100644
--- a/requirements/test.txt
+++ b/requirements/test.txt
@@ -6,6 +6,7 @@ cryptography==3.3.1; platform_machine!="i686" and python_version<"3.9" # no 32-b
 freezegun==1.1.0
 mypy==0.910; implementation_name=="cpython"
 mypy-extensions==0.4.3; implementation_name=="cpython"
+proxy.py==2.3.1
 pytest==6.2.2
 pytest-cov==2.12.1
 pytest-mock==3.6.1
diff --git a/tests/test_proxy_functional.py b/tests/test_proxy_functional.py
index e1c3c0095e7..bde34b2ba8f 100644
--- a/tests/test_proxy_functional.py
+++ b/tests/test_proxy_functional.py
@@ -5,12 +5,142 @@
 from typing import Any
 from unittest import mock
 
+import proxy
 import pytest
 from yarl import URL
 
 import aiohttp
 from aiohttp import web
 
+ASYNCIO_SUPPORTS_TLS_IN_TLS = hasattr(
+    asyncio.sslproto._SSLProtocolTransport,
+    "_start_tls_compatible",
+)
+
+
+@pytest.fixture
+def secure_proxy_url(monkeypatch, tls_certificate_pem_path):
+    """Return the URL of an instance of a running secure proxy.
+
+    This fixture also spawns that instance and tears it down after the test.
+    """
+    proxypy_args = [
+        "--threadless",  # use asyncio
+        "--num-workers",
+        "1",  # the tests only send one query anyway
+        "--hostname",
+        "127.0.0.1",  # network interface to listen to
+        "--port",
+        0,  # ephemeral port, so that kernel allocates a free one
+        "--cert-file",
+        tls_certificate_pem_path,  # contains both key and cert
+        "--key-file",
+        tls_certificate_pem_path,  # contains both key and cert
+    ]
+
+    class PatchedAccetorPool(proxy.core.acceptor.AcceptorPool):
+        def listen(self):
+            super().listen()
+            self.socket_host, self.socket_port = self.socket.getsockname()[:2]
+
+    monkeypatch.setattr(proxy.proxy, "AcceptorPool", PatchedAccetorPool)
+
+    with proxy.Proxy(input_args=proxypy_args) as proxy_instance:
+        yield URL.build(
+            scheme="https",
+            host=proxy_instance.acceptors.socket_host,
+            port=proxy_instance.acceptors.socket_port,
+        )
+
+
+@pytest.fixture
+def web_server_endpoint_payload():
+    return "Test message"
+
+
+@pytest.fixture(params=("http", "https"))
+def web_server_endpoint_type(request):
+    return request.param
+
+
+@pytest.fixture
+async def web_server_endpoint_url(
+    aiohttp_server,
+    ssl_ctx,
+    web_server_endpoint_payload,
+    web_server_endpoint_type,
+):
+    server_kwargs = (
+        {
+            "ssl": ssl_ctx,
+        }
+        if web_server_endpoint_type == "https"
+        else {}
+    )
+
+    async def handler(*args, **kwargs):
+        return web.Response(text=web_server_endpoint_payload)
+
+    app = web.Application()
+    app.router.add_route("GET", "/", handler)
+    server = await aiohttp_server(app, **server_kwargs)
+
+    return URL.build(
+        scheme=web_server_endpoint_type,
+        host=server.host,
+        port=server.port,
+    )
+
+
+@pytest.fixture
+def _pretend_asyncio_supports_tls_in_tls(
+    monkeypatch,
+    web_server_endpoint_type,
+):
+    if web_server_endpoint_type != "https" or ASYNCIO_SUPPORTS_TLS_IN_TLS:
+        return
+
+    # for https://github.com/python/cpython/pull/28073
+    # and https://bugs.python.org/issue37179
+    monkeypatch.setattr(
+        asyncio.sslproto._SSLProtocolTransport,
+        "_start_tls_compatible",
+        True,
+        raising=False,
+    )
+
+
+@pytest.mark.parametrize(
+    "web_server_endpoint_type",
+    (
+        "http",
+        pytest.param("https", marks=pytest.mark.xfail),
+    ),
+)
+@pytest.mark.usefixtures("_pretend_asyncio_supports_tls_in_tls", "loop")
+async def test_secure_https_proxy_absolute_path(
+    client_ssl_ctx,
+    secure_proxy_url,
+    web_server_endpoint_url,
+    web_server_endpoint_payload,
+) -> None:
+    """Test urls can be requested through a secure proxy."""
+    conn = aiohttp.TCPConnector()
+    sess = aiohttp.ClientSession(connector=conn)
+
+    response = await sess.get(
+        web_server_endpoint_url,
+        proxy=secure_proxy_url,
+        ssl=client_ssl_ctx,  # used for both proxy and endpoint connections
+    )
+
+    assert response.status == 200
+    assert await response.text() == web_server_endpoint_payload
+
+    response.close()
+    await sess.close()
+    await conn.close()
+
 
 @pytest.fixture
 def proxy_test_server(aiohttp_raw_server: Any, loop: Any, monkeypatch: Any):