diff --git a/setup.py b/setup.py
index 9951dfcd..7c829265 100644
--- a/setup.py
+++ b/setup.py
@@ -47,6 +47,13 @@ def run_tests(self):
     "wrapt",
     "six>=1.5",
     "yarl",
+    # Support for urllib3 >=2 needs Python >=3.10
+    # so we need to block urllib3 >=2 for Python <3.10 for now.
+    # Note that vcrpy would work fine without any urllib3 around,
+    # so this block and the dependency can be dropped at some point
+    # in the future. For more Details:
+    # https://github.com/kevin1024/vcrpy/pull/699#issuecomment-1551439663
+    "urllib3 <2; python_version <'3.10'",
 ]
 
 tests_require = [
diff --git a/tox.ini b/tox.ini
index 6faa3e8c..0c4dd706 100644
--- a/tox.ini
+++ b/tox.ini
@@ -3,8 +3,9 @@ skip_missing_interpreters=true
 envlist =
   cov-clean,
   lint,
-  {py37,py38,py39,py310,py311}-{requests-urllib3-1,requests-urllib3-2,httplib2,urllib3-1,urllib3-2,tornado4,boto3,aiohttp,httpx},
-  {pypy3}-{requests-urllib3-1,requests-urllib3-2,httplib2,urllib3-1,urllib3-2,tornado4,boto3},
+  {py37,py38,py39,py310,py311}-{requests-urllib3-1,httplib2,urllib3-1,tornado4,boto3,aiohttp,httpx},
+  {py310,py311}-{requests-urllib3-2,urllib3-2},
+  {pypy3}-{requests-urllib3-1,httplib2,urllib3-1,tornado4,boto3},
   {py310}-httpx019,
   cov-report
 
@@ -100,8 +101,8 @@ deps =
     httpx019: httpx==0.19
     {py37,py38,py39,py310}-{httpx}: pytest-asyncio
 depends =
-  lint,{py37,py38,py39,py310,py311,pypy3}-{requests-urllib3-1,requests-urllib3-2,httplib2,urllib3-1,urllib3-2,tornado4,boto3},{py37,py38,py39,py310,py311}-{aiohttp},{py37,py38,py39,py310,py311}-{httpx}: cov-clean
-  cov-report: lint,{py37,py38,py39,py310,py311,pypy3}-{requests-urllib3-1,requests-urllib3-2,httplib2,urllib3-1,urllib3-2,tornado4,boto3},{py37,py38,py39,py310,py311}-{aiohttp}
+  lint,{py37,py38,py39,py310,py311,pypy3}-{requests-urllib3-1,httplib2,urllib3-1,tornado4,boto3},{py310,py311}-{requests-urllib3-2,urllib3-2},{py37,py38,py39,py310,py311}-{aiohttp},{py37,py38,py39,py310,py311}-{httpx}: cov-clean
+  cov-report: lint,{py37,py38,py39,py310,py311,pypy3}-{requests-urllib3-1,httplib2,urllib3-1,tornado4,boto3},{py310,py311}-{requests-urllib3-2,urllib3-2},{py37,py38,py39,py310,py311}-{aiohttp}
 passenv =
     AWS_ACCESS_KEY_ID
     AWS_DEFAULT_REGION