diff --git a/tests/core/customcert/main.py b/tests/core/customcert/main.py
index 72bda60f1..0037eae3a 100644
--- a/tests/core/customcert/main.py
+++ b/tests/core/customcert/main.py
@@ -1,7 +1,8 @@
+from contextlib import suppress
 from os import getenv
-from requests import get
-from requests.exceptions import RequestException
+from requests import RequestException, get
 from traceback import format_exc
+from time import sleep
 
 try:
 
diff --git a/tests/core/customcert/requirements.in b/tests/core/customcert/requirements.in
index 2c24336eb..e63824704 100644
--- a/tests/core/customcert/requirements.in
+++ b/tests/core/customcert/requirements.in
@@ -1 +1,3 @@
 requests==2.31.0
+selenium==4.14.0
+urllib3[socks]==2.0.7
diff --git a/tests/core/customcert/requirements.txt b/tests/core/customcert/requirements.txt
index 99a4d0cfb..dd857f945 100644
--- a/tests/core/customcert/requirements.txt
+++ b/tests/core/customcert/requirements.txt
@@ -4,10 +4,18 @@
 #
 #    pip-compile --allow-unsafe --generate-hashes --strip-extras requirements.in
 #
+attrs==23.1.0 \
+    --hash=sha256:1f28b4522cdc2fb4256ac1a020c78acf9cba2c6b461ccd2c126f3aa8e8335d04 \
+    --hash=sha256:6279836d581513a26f1bf235f9acd333bc9115683f14f7e8fae46c98fc50e015
+    # via
+    #   outcome
+    #   trio
 certifi==2023.7.22 \
     --hash=sha256:539cc1d13202e33ca466e88b2807e29f4c13049d6d87031a3c110744495cb082 \
     --hash=sha256:92d6037539857d8206b8f6ae472e8b77db8058fec5937a1ef3f54304089edbb9
-    # via requests
+    # via
+    #   requests
+    #   selenium
 charset-normalizer==3.3.1 \
     --hash=sha256:06cf46bdff72f58645434d467bf5228080801298fbba19fe268a01b4534467f5 \
     --hash=sha256:0c8c61fb505c7dad1d251c284e712d4e0372cef3b067f7ddf82a7fa82e1e9a93 \
@@ -100,15 +108,66 @@ charset-normalizer==3.3.1 \
     --hash=sha256:f6a02a3c7950cafaadcd46a226ad9e12fc9744652cc69f9e5534f98b47f3bbcf \
     --hash=sha256:fe81b35c33772e56f4b6cf62cf4aedc1762ef7162a31e6ac7fe5e40d0149eb67
     # via requests
+exceptiongroup==1.1.3 \
+    --hash=sha256:097acd85d473d75af5bb98e41b61ff7fe35efe6675e4f9370ec6ec5126d160e9 \
+    --hash=sha256:343280667a4585d195ca1cf9cef84a4e178c4b6cf2274caef9859782b567d5e3
+    # via
+    #   trio
+    #   trio-websocket
+h11==0.14.0 \
+    --hash=sha256:8f19fbbe99e72420ff35c00b27a34cb9937e902a8b810e2c88300c6f0a3b699d \
+    --hash=sha256:e3fe4ac4b851c468cc8363d500db52c2ead036020723024a109d37346efaa761
+    # via wsproto
 idna==3.4 \
     --hash=sha256:814f528e8dead7d329833b91c5faa87d60bf71824cd12a7530b5526063d02cb4 \
     --hash=sha256:90b77e79eaa3eba6de819a0c442c0b4ceefc341a7a2ab77d7562bf49f425c5c2
-    # via requests
+    # via
+    #   requests
+    #   trio
+outcome==1.3.0 \
+    --hash=sha256:588ef4dc10b64e8df160d8d1310c44e1927129a66d6d2ef86845cef512c5f24c \
+    --hash=sha256:7b688fd82db72f4b0bc9e883a00359d4d4179cd97d27f09c9644d0c842ba7786
+    # via trio
+pysocks==1.7.1 \
+    --hash=sha256:08e69f092cc6dbe92a0fdd16eeb9b9ffbc13cadfe5ca4c7bd92ffb078b293299 \
+    --hash=sha256:2725bd0a9925919b9b51739eea5f9e2bae91e83288108a9ad338b2e3a4435ee5 \
+    --hash=sha256:3f8804571ebe159c380ac6de37643bb4685970655d3bba243530d6558b799aa0
+    # via urllib3
 requests==2.31.0 \
     --hash=sha256:58cd2187c01e70e6e26505bca751777aa9f2ee0b7f4300988b709f44e013003f \
     --hash=sha256:942c5a758f98d790eaed1a29cb6eefc7ffb0d1cf7af05c3d2791656dbd6ad1e1
     # via -r requirements.in
+selenium==4.14.0 \
+    --hash=sha256:0d14b0d9842366f38fb5f8f842cf7c042bcfa062affc6a0a86e4d634bdd0fe54 \
+    --hash=sha256:be9824a9354a7fe288e3fad9ceb6a9c65ddc7c44545d23ad0ebf4ce202b19893
+    # via -r requirements.in
+sniffio==1.3.0 \
+    --hash=sha256:e60305c5e5d314f5389259b7f22aaa33d8f7dee49763119234af3755c55b9101 \
+    --hash=sha256:eecefdce1e5bbfb7ad2eeaabf7c1eeb404d7757c379bd1f7e5cce9d8bf425384
+    # via trio
+sortedcontainers==2.4.0 \
+    --hash=sha256:25caa5a06cc30b6b83d11423433f65d1f9d76c4c6a0c90e3379eaa43b9bfdb88 \
+    --hash=sha256:a163dcaede0f1c021485e957a39245190e74249897e2ae4b2aa38595db237ee0
+    # via trio
+trio==0.22.2 \
+    --hash=sha256:3887cf18c8bcc894433420305468388dac76932e9668afa1c49aa3806b6accb3 \
+    --hash=sha256:f43da357620e5872b3d940a2e3589aa251fd3f881b65a608d742e00809b1ec38
+    # via
+    #   selenium
+    #   trio-websocket
+trio-websocket==0.11.1 \
+    --hash=sha256:18c11793647703c158b1f6e62de638acada927344d534e3c7628eedcb746839f \
+    --hash=sha256:520d046b0d030cf970b8b2b2e00c4c2245b3807853ecd44214acd33d74581638
+    # via selenium
 urllib3==2.0.7 \
     --hash=sha256:c97dfde1f7bd43a71c8d2a58e369e9b2bf692d1334ea9f9cae55add7d0dd0f84 \
     --hash=sha256:fdb6d215c776278489906c2f8916e6e7d4f5a9b602ccbcfdf7f016fc8da0596e
-    # via requests
+    # via
+    #   -r requirements.in
+    #   requests
+    #   selenium
+    #   urllib3
+wsproto==1.2.0 \
+    --hash=sha256:ad565f26ecb92588a3e43bc3d96164de84cd9902482b130d0ddbaa9664a85065 \
+    --hash=sha256:b9acddd652b585d75b20477888c56642fdade28bdfd3579aa24a4d2c037dd736
+    # via trio-websocket
diff --git a/tests/core/misc/main.py b/tests/core/misc/main.py
index c7ee48251..93f1f909c 100644
--- a/tests/core/misc/main.py
+++ b/tests/core/misc/main.py
@@ -1,12 +1,36 @@
 from os import getenv
+from contextlib import suppress
 from subprocess import run
-from requests import ConnectionError, get, head, post
+from requests import RequestException, ConnectionError, get, head, post
 from socket import create_connection
 from ssl import CERT_NONE, create_default_context
 from time import sleep
 from traceback import format_exc
 
 try:
+
+    ready = False
+    retries = 0
+    while not ready:
+        with suppress(RequestException):
+            resp = get("http://www.example.com/ready", headers={"Host": "www.example.com"})
+            status_code = resp.status_code
+            text = resp.text
+
+            if resp.status_code >= 500:
+                print("❌ An error occurred with the server, exiting ...", flush=True)
+                exit(1)
+
+            ready = status_code < 400 and text == "ready"
+
+        if retries > 10:
+            print("❌ The service took too long to be ready, exiting ...", flush=True)
+            exit(1)
+        elif not ready:
+            retries += 1
+            print("⚠️ Waiting for the service to be ready, retrying in 5s ...", flush=True)
+            sleep(5)
+
     ssl_generated = getenv("GENERATE_SELF_SIGNED_SSL", "no") == "yes"
     disabled_default_server = getenv("DISABLE_DEFAULT_SERVER", "no") == "yes"
     deny_http_status = getenv("DENY_HTTP_STATUS", "403")