diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index b85873b00..f9aaa3723 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -54,6 +54,7 @@ jobs:
           - Windows
           - macOS
         python-version:
+          - "3.12"
           - "3.11"
           - "3.10"
           - "3.9"
diff --git a/pyproject.toml b/pyproject.toml
index ac3e04ee1..0d5bc63bc 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -20,10 +20,11 @@ classifiers = [
   "Operating System :: OS Independent",
   "Programming Language :: Python :: 3 :: Only",
   "Programming Language :: Python :: 3",
-  "Programming Language :: Python :: 3.10",
-  "Programming Language :: Python :: 3.11",
   "Programming Language :: Python :: 3.8",
   "Programming Language :: Python :: 3.9",
+  "Programming Language :: Python :: 3.10",
+  "Programming Language :: Python :: 3.11",
+  "Programming Language :: Python :: 3.12",
   "Programming Language :: Python :: Implementation :: CPython",
   "Programming Language :: Python :: Implementation :: PyPy",
   "Programming Language :: Python",
@@ -37,7 +38,7 @@ keywords = ["pip", "requirements", "packaging"]
 dependencies = [
   # direct dependencies
   "build >= 1.0.0",
-  "click >= 8",
+  "click >= 8, < 8.2",
   "pip >= 22.2",
   "pyproject_hooks",
   "tomli; python_version < '3.11'",
diff --git a/tests/test_cli_compile.py b/tests/test_cli_compile.py
index 2c939ab0f..afc9c8776 100644
--- a/tests/test_cli_compile.py
+++ b/tests/test_cli_compile.py
@@ -3,6 +3,7 @@
 import hashlib
 import os
 import pathlib
+import re
 import shutil
 import subprocess
 import sys
@@ -2664,7 +2665,7 @@ def test_error_in_pyproject_toml(
     captured = capfd.readouterr()
 
     assert (
-        "`project` must contain ['name'] properties" in captured.err
+        bool(re.search(r"`project` must contain \['[^']+'\] properties", captured.err))
     ) is verbose_option
 
 
diff --git a/tests/test_cli_sync.py b/tests/test_cli_sync.py
index 5e69770fe..cebfd7081 100644
--- a/tests/test_cli_sync.py
+++ b/tests/test_cli_sync.py
@@ -333,7 +333,9 @@ def test_invalid_pip_version_in_python_executable(
     with open(sync.DEFAULT_REQUIREMENTS_FILE, "w") as req_in:
         req_in.write("small-fake-a==1.10.0")
 
-    custom_executable = tmp_path / "custom_executable"
+    # a dummy executable on Windows needs to end in `.exe` in order for
+    # `shutil.which` to find it
+    custom_executable = tmp_path / "custom_executable.exe"
     custom_executable.write_text("")
 
     custom_executable.chmod(0o700)
diff --git a/tests/test_sync.py b/tests/test_sync.py
index e84b598ba..a6b19b83e 100644
--- a/tests/test_sync.py
+++ b/tests/test_sync.py
@@ -168,13 +168,19 @@ def test_diff_should_not_uninstall(fake_dist):
         "pip-tools==1.1.1",
         "pip-review==1.1.1",
         "pkg-resources==0.0.0",
-        "setuptools==34.0.0",
-        "wheel==0.29.0",
         "python==3.0",
-        "distribute==0.1",
         "wsgiref==0.1",
         "argparse==0.1",
     )
+    # on Python 3.12 and above, `ensurepip` and `venv` do not default to installing
+    # 'setuptools' -- as such, `pip` changes behavior on many Python 3.12 environments
+    # to use isolated builds
+    if sys.version_info < (3, 12):
+        ignored += (
+            "setuptools==34.0.0",
+            "wheel==0.29.0",
+            "distribute==0.1",
+        )
     installed = [fake_dist(pkg) for pkg in ignored]
     reqs = []
 
diff --git a/tox.ini b/tox.ini
index 85f3dc685..dba0b4bb2 100644
--- a/tox.ini
+++ b/tox.ini
@@ -15,7 +15,11 @@ extras =
     coverage: coverage
 deps =
     pipsupported: pip==24.2
-    piplowest: pip==22.2.*
+    pipsupported: setuptools <= 75.8.2
+
+    piplowest: pip == 22.2.* ; python_version < "3.12"
+    piplowest: pip == 23.2.* ; python_version >= "3.12"
+
     piplatest: pip
     pipmain: https://github.com/pypa/pip/archive/main.zip
 setenv =