diff --git a/Formula/charm-tools.rb b/Formula/charm-tools.rb
index 0144f1c46f058..22da5f163bcb4 100644
--- a/Formula/charm-tools.rb
+++ b/Formula/charm-tools.rb
@@ -6,6 +6,7 @@ class CharmTools < Formula
   url "https://files.pythonhosted.org/packages/0f/ea/5fa9e1a11e560314e119765b9c7c32a9ffa85caf51769f3d8f812cbc9237/charm-tools-3.0.6.tar.gz"
   sha256 "e783d701d1e32d7b3b356d48238381d0f1f8aa2891d8548d48a921e778825b69"
   license "GPL-3.0-only"
+  revision 1
 
   bottle do
     sha256 cellar: :any,                 arm64_ventura:  "c7cf914b7fa8871bb1a99e32d41a907123115b697f3016e4764d2369a031fafb"
@@ -17,23 +18,23 @@ class CharmTools < Formula
     sha256 cellar: :any_skip_relocation, x86_64_linux:   "6c9dcfa6e8f45aea421281409adff7bf578666bbbcb1969b32a7e95af262a8ac"
   end
 
+  depends_on "pkg-config" => :build
   depends_on "rust" => :build
   depends_on "charm"
   depends_on "libyaml"
   depends_on "openssl@1.1"
-  depends_on "python@3.11"
+  depends_on "python@3.10"
   depends_on "six"
 
   uses_from_macos "libffi"
 
   on_linux do
-    depends_on "pkg-config" => :build
     depends_on "gmp"
   end
 
   resource "attrs" do
-    url "https://files.pythonhosted.org/packages/21/31/3f468da74c7de4fcf9b25591e682856389b3400b4b62f201e65f15ea3e07/attrs-22.2.0.tar.gz"
-    sha256 "c9227bfc2f01993c03f68db37d1d15c9690188323c067c641f1a35ca58185f99"
+    url "https://files.pythonhosted.org/packages/97/90/81f95d5f705be17872843536b1868f351805acf6971251ff07c1b8334dbb/attrs-23.1.0.tar.gz"
+    sha256 "6279836d581513a26f1bf235f9acd333bc9115683f14f7e8fae46c98fc50e015"
   end
 
   resource "blessings" do
@@ -42,8 +43,8 @@ class CharmTools < Formula
   end
 
   resource "certifi" do
-    url "https://files.pythonhosted.org/packages/37/f7/2b1b0ec44fdc30a3d31dfebe52226be9ddc40cd6c0f34ffc8923ba423b69/certifi-2022.12.7.tar.gz"
-    sha256 "35824b4c3a97115964b408844d64aa14db1cc518f6562e8d7261699d1350a9e3"
+    url "https://files.pythonhosted.org/packages/93/71/752f7a4dd4c20d6b12341ed1732368546bc0ca9866139fe812f6009d9ac7/certifi-2023.5.7.tar.gz"
+    sha256 "0f0d56dc5a6ad56fd4ba36484d6cc34451e1c6548c61daad8c320169f91eddc7"
   end
 
   resource "cffi" do
@@ -56,7 +57,7 @@ class CharmTools < Formula
     sha256 "34e0a2f9c370eb95597aae63bf85eb5e96826d81e3dcf88b8886012906f509b5"
   end
 
-  resource "Cheetah3" do
+  resource "cheetah3" do
     url "https://files.pythonhosted.org/packages/23/33/ace0250068afca106c1df34348ab0728e575dc9c61928d216de3e381c460/Cheetah3-3.2.6.post1.tar.gz"
     sha256 "58b5d84e5fbff6cf8e117414b3ea49ef51654c02ee887d155113c5b91d761967"
   end
@@ -67,8 +68,8 @@ class CharmTools < Formula
   end
 
   resource "cryptography" do
-    url "https://files.pythonhosted.org/packages/fa/f3/f4b8c175ea9a1de650b0085858059050b7953a93d66c97ed89b93b232996/cryptography-39.0.2.tar.gz"
-    sha256 "bc5b871e977c8ee5a1bbc42fa8d19bcc08baf0c51cbf1586b0e87a2694dde42f"
+    url "https://files.pythonhosted.org/packages/f7/80/04cc7637238b78f8e7354900817135c5a23cf66dfb3f3a216c6d630d6833/cryptography-40.0.2.tar.gz"
+    sha256 "c33c0d32b8594fa647d2e01dbccc303478e16fdd7cf98652d5b3ed11aa5e5c99"
   end
 
   resource "dict2colander" do
@@ -82,8 +83,8 @@ class CharmTools < Formula
   end
 
   resource "filelock" do
-    url "https://files.pythonhosted.org/packages/4f/1f/6e1b740698069650b245744957a25957d599b953550a959ab2a584a8825b/filelock-3.10.0.tar.gz"
-    sha256 "3199fd0d3faea8b911be52b663dfccceb84c95949dd13179aa21436d1a79c4ce"
+    url "https://files.pythonhosted.org/packages/24/85/cf4df939cc0a037ebfe18353005e775916faec24dcdbc7a2f6539ad9d943/filelock-3.12.0.tar.gz"
+    sha256 "fc03ae43288c013d2ea83c8597001b1129db351aad9c57fe2409327916b8e718"
   end
 
   resource "idna" do
@@ -92,8 +93,8 @@ class CharmTools < Formula
   end
 
   resource "importlib-metadata" do
-    url "https://files.pythonhosted.org/packages/90/07/6397ad02d31bddf1841c9ad3ec30a693a3ff208e09c2ef45c9a8a5f85156/importlib_metadata-6.0.0.tar.gz"
-    sha256 "e354bedeb60efa6affdcc8ae121b73544a7aa74156d047311948f6d711cd378d"
+    url "https://files.pythonhosted.org/packages/0b/1f/9de392c2b939384e08812ef93adf37684ec170b5b6e7ea302d9f163c2ea0/importlib_metadata-6.6.0.tar.gz"
+    sha256 "92501cdf9cc66ebd3e612f1b4f0c0765dfa42f0fa38ffb319b6bd84dd675d705"
   end
 
   resource "iso8601" do
@@ -101,7 +102,7 @@ class CharmTools < Formula
     sha256 "32811e7b81deee2063ea6d2e94f8819a86d1f3811e49d23623a41fa832bef03f"
   end
 
-  resource "jaraco.classes" do
+  resource "jaraco-classes" do
     url "https://files.pythonhosted.org/packages/bf/02/a956c9bfd2dfe60b30c065ed8e28df7fcf72b292b861dca97e951c145ef6/jaraco.classes-3.2.3.tar.gz"
     sha256 "89559fa5c1d3c34eff6f631ad80bb21f378dbcbb35dd161fd2c6b93f5be2f98a"
   end
@@ -146,7 +147,7 @@ class CharmTools < Formula
     sha256 "bea3816e1d54f4e33aac78d2031a0b0ed2f95e69db85b45d51f17df97071da69"
   end
 
-  resource "path.py" do
+  resource "path-py" do
     url "https://files.pythonhosted.org/packages/b6/e3/81be70016d58ade0f516191fa80152daba5453d0b07ce648d9daae86a188/path.py-12.5.0.tar.gz"
     sha256 "8d885e8b2497aed005703d94e0fd97943401f035e42a136810308bff034529a8"
   end
@@ -157,8 +158,8 @@ class CharmTools < Formula
   end
 
   resource "platformdirs" do
-    url "https://files.pythonhosted.org/packages/79/c4/f98a05535344f79699bbd494e56ac9efc986b7a253fe9f4dba7414a7f505/platformdirs-3.1.1.tar.gz"
-    sha256 "024996549ee88ec1a9aa99ff7f8fc819bb59e2c3477b410d90a16d32d6e707aa"
+    url "https://files.pythonhosted.org/packages/9c/0e/ae9ef1049d4b5697e79250c4b2e72796e4152228e67733389868229c92bb/platformdirs-3.5.1.tar.gz"
+    sha256 "412dae91f52a6f84830f39a8078cecd0e866cb72294a5c66808e74d5e88d251f"
   end
 
   resource "pycparser" do
@@ -171,14 +172,14 @@ class CharmTools < Formula
     sha256 "1a2994773706bbb4995c31a97bc94f1418314923bd1048c6d964837040376440"
   end
 
-  resource "PyYAML" do
+  resource "pyyaml" do
     url "https://files.pythonhosted.org/packages/a0/a4/d63f2d7597e1a4b55aa3b4d6c5b029991d3b824b5bd331af8d4ab1ed687d/PyYAML-5.4.1.tar.gz"
     sha256 "607774cbba28732bfa802b54baa7484215f530991055bb562efbed5b2f20a45e"
   end
 
   resource "requests" do
-    url "https://files.pythonhosted.org/packages/9d/ee/391076f5937f0a8cdf5e53b701ffc91753e87b07d66bae4a09aa671897bf/requests-2.28.2.tar.gz"
-    sha256 "98b1b2782e3c6c4904938b84c0eb932721069dfdb9134313beff7c83c2df24bf"
+    url "https://files.pythonhosted.org/packages/9d/be/10918a2eac4ae9f02f6cfe6414b7a155ccd8f7f9d4380d62fd5b955065c3/requests-2.31.0.tar.gz"
+    sha256 "942c5a758f98d790eaed1a29cb6eefc7ffb0d1cf7af05c3d2791656dbd6ad1e1"
   end
 
   resource "requirements-parser" do
@@ -186,12 +187,17 @@ class CharmTools < Formula
     sha256 "3336f3a3ae23e06d3f0f88595e4052396e3adf91688787f637e5d2ca1a904069"
   end
 
-  resource "ruamel.yaml" do
-    url "https://files.pythonhosted.org/packages/46/a9/6ed24832095b692a8cecc323230ce2ec3480015fbfa4b79941bd41b23a3c/ruamel.yaml-0.17.21.tar.gz"
-    sha256 "8b7ce697a2f212752a35c1ac414471dc16c424c9573be4926b56ff3f5d23b7af"
+  resource "ruamel-yaml" do
+    url "https://files.pythonhosted.org/packages/8c/0d/32f86bfad2755763b926f988252f57f4edbba32f876cb5e6d6f5c57b5f05/ruamel.yaml-0.17.26.tar.gz"
+    sha256 "baa2d0a5aad2034826c439ce61c142c07082b76f4791d54145e131206e998059"
   end
 
-  resource "SecretStorage" do
+  resource "ruamel-yaml-clib" do
+    url "https://files.pythonhosted.org/packages/d5/31/a3e6411947eb7a4f1c669f887e9e47d61a68f9d117f10c3c620296694a0b/ruamel.yaml.clib-0.2.7.tar.gz"
+    sha256 "1f08fd5a2bea9c4180db71678e850b995d2a5f4537be0e94557668cf0f5f9497"
+  end
+
+  resource "secretstorage" do
     url "https://files.pythonhosted.org/packages/53/a4/f48c9d79cb507ed1373477dbceaba7401fd8a23af63b837fa61f1dcd3691/SecretStorage-3.3.3.tar.gz"
     sha256 "2403533ef369eca6d2ba81718576c5e0f564d5cca1b58f73a8b23e7d4eeebd77"
   end
@@ -207,13 +213,13 @@ class CharmTools < Formula
   end
 
   resource "types-setuptools" do
-    url "https://files.pythonhosted.org/packages/9e/08/99563df1520cbea98ba0d9c2384d44f4b324092d7aeb99899b7455a9aafb/types-setuptools-67.6.0.0.tar.gz"
-    sha256 "70b5e6a379e9fccf6579871a93ca3301a46252e3ae66957ec64281a2b6a812d9"
+    url "https://files.pythonhosted.org/packages/9f/b1/01280c629276c7fec2580ba90b48955397a178d899936567a9ab98ba5afe/types-setuptools-67.8.0.0.tar.gz"
+    sha256 "95c9ed61871d6c0e258433373a4e1753c0a7c3627a46f4d4058c7b5a08ab844f"
   end
 
   resource "urllib3" do
-    url "https://files.pythonhosted.org/packages/21/79/6372d8c0d0641b4072889f3ff84f279b738cd8595b64c8e0496d4e848122/urllib3-1.26.15.tar.gz"
-    sha256 "8a388717b9476f934a21484e8c8e61875ab60644d29b9b39e11e4b9dc1c6b305"
+    url "https://files.pythonhosted.org/packages/fb/c0/1abba1a1233b81cf2e36f56e05194f5e8a0cec8c03c244cab56cc9dfb5bd/urllib3-2.0.2.tar.gz"
+    sha256 "61717a1095d7e155cdb737ac7bb2f4324a858a1e2e6466f6d03ff630ca68d3cc"
   end
 
   resource "vergit" do
@@ -222,8 +228,8 @@ class CharmTools < Formula
   end
 
   resource "virtualenv" do
-    url "https://files.pythonhosted.org/packages/87/14/ca9890d58cd33d9122eb87ffec2f3c6be0714785f992a0fd3b56a3b6c993/virtualenv-20.21.0.tar.gz"
-    sha256 "f50e3e60f990a0757c9b68333c9fdaa72d7188caa417f96af9e52407831a3b68"
+    url "https://files.pythonhosted.org/packages/d6/37/3ff25b2ad0d51cfd752dc68ee0ad4387f058a5ceba4d89b47ac478de3f59/virtualenv-20.23.0.tar.gz"
+    sha256 "a85caa554ced0c0afbd0d638e7e2d7b5f92d23478d05d17a76daeac8f279f924"
   end
 
   resource "wheel" do