diff --git a/.gitignore b/.gitignore
index 096c31dd2..9ccbae27f 100644
--- a/.gitignore
+++ b/.gitignore
@@ -62,3 +62,6 @@ certbot-dns*/certbot-dns*_arm*.txt
 /certbot_arm*.txt
 certbot-dns*/snap
 snapcraft.cfg
+
+# pyenv files
+.python-version
diff --git a/certbot-dns-digitalocean/setup.py b/certbot-dns-digitalocean/setup.py
index bfe2f60e6..1e5045448 100644
--- a/certbot-dns-digitalocean/setup.py
+++ b/certbot-dns-digitalocean/setup.py
@@ -5,7 +5,7 @@ from setuptools import setup
 version = '5.0.0.dev0'
 
 install_requires = [
-    'python-digitalocean>=1.11', # 1.15.0 or newer is recommended for TTL support
+    'python-digitalocean>=1.15.0', # 1.15.0 or newer is recommended for TTL support
 ]
 
 if os.environ.get('SNAP_BUILD'):
diff --git a/certbot/pyproject.toml b/certbot/pyproject.toml
index 578cacb23..fb6e6f107 100644
--- a/certbot/pyproject.toml
+++ b/certbot/pyproject.toml
@@ -68,6 +68,7 @@ test = [
     "types-pywin32",
     "types-requests",
     "types-setuptools",
+    "uv",
     "wheel",
 ]
 all = [
diff --git a/certbot/setup.py b/certbot/setup.py
index 71bb62540..39d869db6 100644
--- a/certbot/setup.py
+++ b/certbot/setup.py
@@ -33,7 +33,7 @@ install_requires = [
     'distro>=1.0.1',
     'importlib_metadata>=8.6.1; python_version < "3.10"',
     'josepy>=2.0.0',
-    'parsedatetime>=2.4',
+    'parsedatetime>=2.6',
     'pyrfc3339',
     # This dependency needs to be added using environment markers to avoid its
     # installation on Linux.
diff --git a/newsfragments/10428.added b/newsfragments/10428.added
new file mode 100644
index 000000000..7e50dbc70
--- /dev/null
+++ b/newsfragments/10428.added
@@ -0,0 +1 @@
+Added `uv` as a test dependency, and switched most `pip` invocations to `uv pip` for faster installs.
diff --git a/tools/oldest_constraints.txt b/tools/oldest_constraints.txt
index 753fb22e8..d24c4f36d 100644
--- a/tools/oldest_constraints.txt
+++ b/tools/oldest_constraints.txt
@@ -15,7 +15,7 @@ cloudflare==2.19.0 ; python_version == "3.10"
 colorama==0.4.6 ; (sys_platform == "win32" or platform_system == "Windows") and python_version == "3.10"
 configargparse==1.5.3 ; python_version == "3.10"
 configobj==5.0.6 ; python_version == "3.10"
-coverage==7.10.3 ; python_version == "3.10"
+coverage==7.10.4 ; python_version == "3.10"
 cryptography==43.0.0 ; python_version == "3.10"
 cython==0.29.37 ; python_version == "3.10"
 dill==0.4.0 ; python_version == "3.10"
@@ -25,9 +25,8 @@ dns-lexicon==3.15.1 ; python_version == "3.10"
 dnspython==2.6.1 ; python_version == "3.10"
 exceptiongroup==1.3.0 ; python_version == "3.10"
 execnet==2.1.1 ; python_version == "3.10"
-filelock==3.18.0 ; python_version == "3.10"
+filelock==3.19.1 ; python_version == "3.10"
 funcsigs==0.4 ; python_version == "3.10"
-future==1.0.0 ; python_version == "3.10"
 google-api-python-client==1.6.5 ; python_version == "3.10"
 google-auth==2.16.0 ; python_version == "3.10"
 httplib2==0.9.2 ; python_version == "3.10"
@@ -38,13 +37,14 @@ isort==6.0.1 ; python_version == "3.10"
 jmespath==0.10.0 ; python_version == "3.10"
 josepy==2.1.0 ; python_version == "3.10"
 jsonlines==4.0.0 ; python_version == "3.10"
+jsonpickle==4.1.1 ; python_version == "3.10"
 mccabe==0.7.0 ; python_version == "3.10"
 mypy-extensions==1.1.0 ; python_version == "3.10"
 mypy==1.17.1 ; python_version == "3.10"
 ndg-httpsclient==0.3.2 ; python_version == "3.10"
 oauth2client==4.1.3 ; python_version == "3.10"
 packaging==25.0 ; python_version == "3.10"
-parsedatetime==2.4 ; python_version == "3.10"
+parsedatetime==2.6 ; python_version == "3.10"
 pathspec==0.12.1 ; python_version == "3.10"
 pbr==1.8.0 ; python_version == "3.10"
 pip==25.2 ; python_version == "3.10"
@@ -66,14 +66,14 @@ pytest-xdist==3.8.0 ; python_version == "3.10"
 pytest==8.4.1 ; python_version == "3.10"
 python-augeas==0.5.0 ; python_version == "3.10"
 python-dateutil==2.9.0.post0 ; python_version == "3.10"
-python-digitalocean==1.11 ; python_version == "3.10"
+python-digitalocean==1.15.0 ; python_version == "3.10"
 pytz==2025.2 ; python_version == "3.10"
 pywin32==311 ; python_version == "3.10" and sys_platform == "win32"
 pyyaml==6.0.2 ; python_version == "3.10"
 requests-file==2.1.0 ; python_version == "3.10"
 requests==2.25.1 ; python_version == "3.10"
 rsa==4.9.1 ; python_version == "3.10"
-ruff==0.12.8 ; python_version == "3.10"
+ruff==0.12.9 ; python_version == "3.10"
 s3transfer==0.5.2 ; python_version == "3.10"
 setuptools==80.9.0 ; python_version == "3.10"
 six==1.16.0 ; python_version == "3.10"
@@ -92,5 +92,6 @@ types-urllib3==1.26.25.14 ; python_version == "3.10"
 typing-extensions==4.14.1 ; python_version == "3.10"
 uritemplate==3.0.1 ; python_version == "3.10"
 urllib3==1.26.5 ; python_version == "3.10"
+uv==0.8.11 ; python_version == "3.10"
 virtualenv==20.34.0 ; python_version == "3.10"
 wheel==0.45.1 ; python_version == "3.10"
diff --git a/tools/pinning/oldest/pyproject.toml b/tools/pinning/oldest/pyproject.toml
index 38510921f..ec027247c 100644
--- a/tools/pinning/oldest/pyproject.toml
+++ b/tools/pinning/oldest/pyproject.toml
@@ -72,7 +72,7 @@ httplib2 = "0.9.2"
 idna = "2.6"
 ipaddress = "1.0.16"
 ndg-httpsclient = "0.3.2"
-parsedatetime = "2.4"
+parsedatetime = "2.6"
 pbr = "1.8.0"
 ply = "3.4"
 pyOpenSSL = "25.0.0"
@@ -81,7 +81,7 @@ pyasn1 = "0.4.8"
 pycparser = "2.14"
 pyparsing = "2.4.7"
 python-augeas = "0.5.0"
-python-digitalocean = "1.11"
+python-digitalocean = "1.15.0"
 requests = "2.25.1"
 six = "1.16.0"
 urllib3 = "1.26.5"
diff --git a/tools/pip_install.py b/tools/pip_install.py
index ebec4baef..dc74f2ed5 100755
--- a/tools/pip_install.py
+++ b/tools/pip_install.py
@@ -28,6 +28,10 @@ def call_with_print(command, env):
     subprocess.check_call(command, shell=True, env=env)
 
 
+def uv_install_with_print(args_str, env):
+    command = ['"', sys.executable, '" -m uv pip install ', args_str]
+    call_with_print(''.join(command), env=env)
+
 def pip_install_with_print(args_str, env):
     command = ['"', sys.executable, '" -m pip install --disable-pip-version-check --use-pep517 ', args_str]
     call_with_print(''.join(command), env=env)
@@ -49,19 +53,21 @@ def pip_constrained_environ():
     # are also used when installing build dependencies. See
     # https://github.com/certbot/certbot/pull/8443 for more info.
     env["PIP_CONSTRAINT"] = constraints_path
+    env["UV_CONSTRAINT"] = constraints_path
+    env["UV_BUILD_CONSTRAINT"] = constraints_path
     return env
 
 
 def pipstrap(env=None):
     if env is None:
         env = pip_constrained_environ()
-    pip_install_with_print('pip setuptools wheel', env=env)
+    pip_install_with_print('pip setuptools wheel uv', env=env)
 
 
 def main(args):
     env = pip_constrained_environ()
     pipstrap(env)
-    pip_install_with_print(' '.join(args), env=env)
+    uv_install_with_print(' '.join(args), env=env)
 
 
 if __name__ == '__main__':
diff --git a/tools/requirements.txt b/tools/requirements.txt
index 0fee425a3..5a96e9d63 100644
--- a/tools/requirements.txt
+++ b/tools/requirements.txt
@@ -17,8 +17,8 @@ babel==2.17.0 ; python_version >= "3.10" and python_version < "4.0"
 backports-tarfile==1.2.0 ; python_version >= "3.10" and python_version < "3.12"
 bcrypt==4.3.0 ; python_version >= "3.10" and python_version < "4.0"
 beautifulsoup4==4.13.4 ; python_version >= "3.10" and python_version < "4.0"
-boto3==1.40.8 ; python_version >= "3.10" and python_version < "4.0"
-botocore==1.40.8 ; python_version >= "3.10" and python_version < "4.0"
+boto3==1.40.11 ; python_version >= "3.10" and python_version < "4.0"
+botocore==1.40.11 ; python_version >= "3.10" and python_version < "4.0"
 build==1.3.0 ; python_version >= "3.10" and python_version < "4.0"
 cachecontrol==0.14.3 ; python_version >= "3.10" and python_version < "4.0"
 cachetools==5.5.2 ; python_version >= "3.10" and python_version < "4.0"
@@ -32,7 +32,7 @@ cloudflare==2.19.4 ; python_version >= "3.10" and python_version < "4.0"
 colorama==0.4.6 ; python_version >= "3.10" and python_version < "4.0"
 configargparse==1.7.1 ; python_version >= "3.10" and python_version < "4.0"
 configobj==5.0.9 ; python_version >= "3.10" and python_version < "4.0"
-coverage==7.10.3 ; python_version >= "3.10" and python_version < "4.0"
+coverage==7.10.4 ; python_version >= "3.10" and python_version < "4.0"
 crashtest==0.4.1 ; python_version >= "3.10" and python_version < "4.0"
 cryptography==45.0.6 ; python_version >= "3.10" and python_version < "4.0"
 cython==0.29.37 ; python_version >= "3.10" and python_version < "4.0"
@@ -49,11 +49,11 @@ exceptiongroup==1.3.0 ; python_version == "3.10"
 execnet==2.1.1 ; python_version >= "3.10" and python_version < "4.0"
 executing==2.2.0 ; python_version >= "3.10" and python_version < "4.0"
 fabric==3.2.2 ; python_version >= "3.10" and python_version < "4.0"
-fastjsonschema==2.21.1 ; python_version >= "3.10" and python_version < "4.0"
-filelock==3.18.0 ; python_version >= "3.10" and python_version < "4.0"
+fastjsonschema==2.21.2 ; python_version >= "3.10" and python_version < "4.0"
+filelock==3.19.1 ; python_version >= "3.10" and python_version < "4.0"
 findpython==0.6.3 ; python_version >= "3.10" and python_version < "4.0"
 google-api-core==2.25.1 ; python_version >= "3.10" and python_version < "4.0"
-google-api-python-client==2.178.0 ; python_version >= "3.10" and python_version < "4.0"
+google-api-python-client==2.179.0 ; python_version >= "3.10" and python_version < "4.0"
 google-auth-httplib2==0.2.0 ; python_version >= "3.10" and python_version < "4.0"
 google-auth==2.40.3 ; python_version >= "3.10" and python_version < "4.0"
 googleapis-common-protos==1.70.0 ; python_version >= "3.10" and python_version < "4.0"
@@ -101,7 +101,7 @@ packaging==25.0 ; python_version >= "3.10" and python_version < "4.0"
 paramiko==4.0.0 ; python_version >= "3.10" and python_version < "4.0"
 parsedatetime==2.6 ; python_version >= "3.10" and python_version < "4.0"
 parso==0.8.4 ; python_version >= "3.10" and python_version < "4.0"
-pbs-installer==2025.8.8 ; python_version >= "3.10" and python_version < "4.0"
+pbs-installer==2025.8.14 ; python_version >= "3.10" and python_version < "4.0"
 pexpect==4.9.0 ; python_version >= "3.10" and python_version < "4.0" and sys_platform != "win32" and sys_platform != "emscripten"
 pip==25.2 ; python_version >= "3.10" and python_version < "4.0"
 pkginfo==1.12.1.2 ; python_version >= "3.10" and python_version < "4.0"
@@ -113,7 +113,7 @@ poetry-plugin-export==1.9.0 ; python_version >= "3.10" and python_version < "4.0
 poetry==2.1.4 ; python_version >= "3.10" and python_version < "4.0"
 prompt-toolkit==3.0.51 ; python_version >= "3.10" and python_version < "4.0"
 proto-plus==1.26.1 ; python_version >= "3.10" and python_version < "4.0"
-protobuf==6.31.1 ; python_version >= "3.10" and python_version < "4.0"
+protobuf==6.32.0 ; python_version >= "3.10" and python_version < "4.0"
 ptyprocess==0.7.0 ; python_version >= "3.10" and python_version < "4.0" and sys_platform != "win32" and sys_platform != "emscripten"
 pure-eval==0.2.3 ; python_version >= "3.10" and python_version < "4.0"
 pyasn1-modules==0.4.2 ; python_version >= "3.10" and python_version < "4.0"
@@ -147,7 +147,7 @@ rfc3986==2.0.0 ; python_version >= "3.10" and python_version < "4.0"
 rich==14.1.0 ; python_version >= "3.10" and python_version < "4.0"
 roman-numerals-py==3.1.0 ; python_version >= "3.11" and python_version < "4.0"
 rsa==4.9.1 ; python_version >= "3.10" and python_version < "4.0"
-ruff==0.12.8 ; python_version >= "3.10" and python_version < "4.0"
+ruff==0.12.9 ; python_version >= "3.10" and python_version < "4.0"
 s3transfer==0.13.1 ; python_version >= "3.10" and python_version < "4.0"
 secretstorage==3.3.3 ; python_version >= "3.10" and python_version < "4.0" and sys_platform == "linux"
 semantic-version==2.10.0 ; python_version >= "3.10" and python_version < "4.0"
@@ -186,10 +186,11 @@ types-setuptools==80.9.0.20250809 ; python_version >= "3.10" and python_version
 typing-extensions==4.14.1 ; python_version >= "3.10" and python_version < "4.0"
 uritemplate==4.2.0 ; python_version >= "3.10" and python_version < "4.0"
 urllib3==2.5.0 ; python_version >= "3.10" and python_version < "4.0"
+uv==0.8.11 ; python_version >= "3.10" and python_version < "4.0"
 virtualenv==20.32.0 ; python_version >= "3.10" and python_version < "4.0"
 wcwidth==0.2.13 ; python_version >= "3.10" and python_version < "4.0"
 wheel==0.45.1 ; python_version >= "3.10" and python_version < "4.0"
 wrapt==1.17.3 ; python_version >= "3.10" and python_version < "4.0"
 xattr==1.2.0 ; python_version >= "3.10" and python_version < "4.0" and sys_platform == "darwin"
 zipp==3.23.0 ; python_version >= "3.10" and python_version < "3.12"
-zstandard==0.23.0 ; python_version >= "3.10" and python_version < "4.0"
+zstandard==0.24.0 ; python_version >= "3.10" and python_version < "4.0"