diff --git a/tools/pinning/current/pyproject.toml b/tools/pinning/current/pyproject.toml
index 0625c1a9a..ef97fb455 100644
--- a/tools/pinning/current/pyproject.toml
+++ b/tools/pinning/current/pyproject.toml
@@ -64,10 +64,6 @@ mypy = "<0.900"
 # needed. This dependency can be removed here once Certbot's support for the
 # 3rd party mock library has been dropped.
 mock = "*"
-# pip's new dependency resolver fails on local packages that depend on each
-# other when those packages are requested with extras such as 'certbot[dev]' so
-# let's pin it back for now. See https://github.com/pypa/pip/issues/9204.
-pip = "20.2.4"
 # poetry 1.2.0+ is required for it to pin pip, setuptools, and wheel. See
 # https://github.com/python-poetry/poetry/issues/1584. This version is required
 # here in addition to certbot/setup.py because otherwise the pre-release
diff --git a/tools/requirements.txt b/tools/requirements.txt
index 81843cab0..93e7c6112 100644
--- a/tools/requirements.txt
+++ b/tools/requirements.txt
@@ -9,18 +9,18 @@ alabaster==0.7.12; python_version >= "3.6"
 apacheconfig==0.3.2; python_version >= "3.6"
 appdirs==1.4.4; python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" or python_version >= "3.6" and python_version < "4.0" and python_full_version >= "3.4.0"
 appnope==0.1.2; python_version == "3.6" and sys_platform == "darwin" or python_version >= "3.7" and sys_platform == "darwin"
-astroid==2.6.5; python_version >= "3.6" and python_version < "4.0"
+astroid==2.6.6; python_version >= "3.6" and python_version < "4.0"
 atomicwrites==1.4.0; python_version >= "3.6" and python_full_version < "3.0.0" and sys_platform == "win32" or sys_platform == "win32" and python_version >= "3.6" and python_full_version >= "3.4.0"
 attrs==21.2.0; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.5.0" and python_version >= "3.6"
-awscli==1.20.12; python_version >= "3.6"
+awscli==1.20.22; python_version >= "3.6"
 azure-devops==6.0.0b4; python_version >= "3.6"
 babel==2.9.1; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.4.0"
 backcall==0.2.0; python_version == "3.6" or python_version >= "3.7"
 bcrypt==3.2.0; python_version >= "3.6"
 beautifulsoup4==4.9.3; python_version >= "3.6" and python_version < "4.0" or python_version >= "3.6"
-bleach==3.3.1; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.5.0"
-boto3==1.18.12; python_version >= "3.6"
-botocore==1.21.12; python_version >= "3.6"
+bleach==4.0.0; python_version >= "3.6"
+boto3==1.18.22; python_version >= "3.6"
+botocore==1.21.22; python_version >= "3.6"
 cachecontrol==0.12.6; python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" or python_version >= "3.6" and python_version < "4.0" and python_full_version >= "3.4.0"
 cached-property==1.5.2; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.4.0" and python_version >= "3.6"
 cachetools==4.2.2; python_version >= "3.5" and python_version < "4.0" and (python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.6.0" and python_version >= "3.6")
@@ -32,7 +32,7 @@ charset-normalizer==2.0.4; python_full_version >= "3.6.0" and python_version >=
 cleo==1.0.0a4; python_version >= "3.6" and python_version < "4.0"
 cloudflare==2.8.15; python_version >= "3.6"
 colorama==0.4.3; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.5.0" and python_version >= "3.6" or python_version >= "3.6" and python_full_version < "3.0.0" and sys_platform == "win32" or sys_platform == "win32" and python_version >= "3.6" and python_full_version >= "3.5.0" or python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" and sys_platform == "win32" or python_version >= "3.6" and python_version < "4.0" and sys_platform == "win32" and python_full_version >= "3.5.0" or python_version >= "3.6" and python_full_version < "3.0.0" and platform_system == "Windows" or python_version >= "3.6" and python_full_version >= "3.5.0" and platform_system == "Windows" or python_version == "3.6" and python_full_version < "3.0.0" and sys_platform == "win32" or python_version == "3.6" and sys_platform == "win32" and python_full_version >= "3.5.0" or python_version >= "3.7" and python_full_version < "3.0.0" and sys_platform == "win32" or python_version >= "3.7" and sys_platform == "win32" and python_full_version >= "3.5.0"
-configargparse==1.5.1; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.5.0" and python_version >= "3.6"
+configargparse==1.5.2; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.5.0" and python_version >= "3.6"
 configobj==5.0.6; python_version >= "3.6"
 coverage==5.5; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.5.0" and python_version < "4" and python_version >= "3.6"
 crashtest==0.3.1; python_version >= "3.6" and python_version < "4.0"
@@ -43,7 +43,7 @@ decorator==5.0.9; python_version == "3.6" or python_version > "3.6" or python_ve
 deprecated==1.2.12; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.4.0"
 distlib==0.3.2; python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" or python_version >= "3.6" and python_version < "4.0" and python_full_version >= "3.4.0" or python_version >= "3.6"
 distro==1.6.0; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.4.0" and python_version >= "3.6" or python_version >= "3.6"
-dns-lexicon==3.6.1; python_version >= "3.6" and python_version < "4.0"
+dns-lexicon==3.7.0; python_version >= "3.6" and python_version < "4.0"
 dnspython==2.1.0; python_version >= "3.6"
 docker-compose==1.26.2; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.4.0" and python_version >= "3.6"
 docker==4.2.2; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.5.0" and python_version >= "3.6"
@@ -101,13 +101,13 @@ parso==0.8.2; python_version == "3.6"
 pathlib2==2.3.6; python_version >= "3.6"
 pexpect==4.8.0; python_version >= "3.6" and python_version < "4.0" or python_version == "3.6" and sys_platform != "win32" or python_version >= "3.7" and sys_platform != "win32"
 pickleshare==0.7.5; python_version == "3.6" or python_version >= "3.7"
-pip==20.2.4; (python_version >= "2.7" and python_full_version < "3.0.0") or (python_full_version >= "3.5.0")
+pip==21.2.4; python_version >= "3.6"
 pkginfo==1.7.1; python_version >= "3.6" and python_version < "4.0" or python_version >= "3.6"
 pluggy==0.13.1; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.4.0" and python_version >= "3.6" or python_version >= "3.6" and python_full_version >= "3.5.0"
 ply==3.11; python_version >= "3.6"
 poetry-core==1.1.0a6; python_version >= "3.6" and python_version < "4.0"
 poetry==1.2.0a2; python_version >= "3.6" and python_version < "4.0"
-prompt-toolkit==3.0.3; python_version == "3.6" or python_version >= "3.7"
+prompt-toolkit==3.0.19; python_version == "3.6" and python_full_version >= "3.6.1" or python_version >= "3.7" and python_full_version >= "3.6.1"
 protobuf==3.17.3; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.6.0" and python_version >= "3.6"
 ptyprocess==0.7.0; python_version >= "3.6" and python_version < "4.0"
 py==1.10.0; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.4.0" and python_version >= "3.6" or python_version >= "3.6" and python_full_version >= "3.5.0"
@@ -115,7 +115,7 @@ pyasn1-modules==0.2.8; python_version >= "3.6" and python_full_version < "3.0.0"
 pyasn1==0.4.8; python_version >= "3.6" and python_version < "4" or python_version >= "3.6"
 pycparser==2.20; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.4.0" and python_version >= "3.6"
 pygithub==1.55; python_version >= "3.6"
-pygments==2.9.0; python_version >= "3.6" or python_version == "3.6" or python_version >= "3.7"
+pygments==2.10.0; python_version >= "3.6" or python_version == "3.6" or python_version >= "3.7"
 pyjwt==2.1.0; python_version >= "3.6"
 pylev==1.4.0; python_version >= "3.6" and python_version < "4.0"
 pylint==2.9.6; python_version >= "3.6" and python_version < "4.0"
@@ -167,7 +167,7 @@ tldextract==3.1.0; python_version >= "3.6" and python_version < "4.0"
 toml==0.10.2; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.3.0" and python_version >= "3.6" or python_full_version >= "3.5.0" and python_version >= "3.6" or python_version == "3.6" and python_full_version < "3.0.0" or python_version > "3.6" and python_full_version < "3.0.0" or python_version == "3.6" and python_full_version >= "3.3.0" or python_version > "3.6" and python_full_version >= "3.3.0" or python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" or python_version >= "3.6" and python_version < "4.0" and python_full_version >= "3.3.0"
 tomlkit==0.7.2; python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" or python_version >= "3.6" and python_version < "4.0" and python_full_version >= "3.5.0"
 tox==3.24.1; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.5.0"
-tqdm==4.62.0; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.4.0"
+tqdm==4.62.1; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.4.0"
 traitlets==4.3.3
 twine==3.3.0; python_version >= "3.6"
 typed-ast==1.4.3; python_version >= "3.6" or implementation_name == "cpython" and python_version < "3.8" and python_version >= "3.6"
@@ -175,10 +175,10 @@ typing-extensions==3.10.0.0; python_version >= "3.6" or python_version >= "3.6"
 uritemplate==3.0.1; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.4.0" and python_version >= "3.6"
 urllib3==1.26.6; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.6.0" and python_version < "4" and python_version >= "3.6" or python_full_version >= "3.5.0" and python_version < "4" and python_version >= "3.6"
 virtualenv==20.4.4; python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" or python_version >= "3.6" and python_version < "4.0" and python_full_version >= "3.4.0" or python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.5.0"
-wcwidth==0.2.5; python_version == "3.6"
-webencodings==0.5.1; python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" or python_version >= "3.6" and python_version < "4.0" and python_full_version >= "3.5.0" or python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.5.0"
+wcwidth==0.2.5; python_version == "3.6" and python_full_version >= "3.6.1"
+webencodings==0.5.1; python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "4.0" or python_version >= "3.6" and python_version < "4.0" and python_full_version >= "3.5.0" or python_version >= "3.6"
 websocket-client==0.59.0; python_version >= "3.6" and python_full_version < "3.0.0" or python_full_version >= "3.4.0" and python_version >= "3.6" or python_full_version >= "3.5.0" and python_version >= "3.6"
-wheel==0.36.2; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.5.0"
+wheel==0.37.0; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.5.0"
 wrapt==1.12.1; python_version >= "3.6" and python_full_version < "3.0.0" or python_version >= "3.6" and python_full_version >= "3.4.0" or python_version >= "3.6" and python_version < "4.0"
 yarg==0.1.9; python_version >= "3.6"
 zipp==3.5.0; python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "3.8" or python_version >= "3.6" and python_version < "3.8" and python_full_version >= "3.5.0" or python_version >= "3.6" and python_full_version < "3.0.0" and python_version < "3.7" or python_version >= "3.6" and python_version < "3.7" and python_full_version >= "3.4.0"