diff --git a/pkgs/by-name/aw/awscli/package.nix b/pkgs/by-name/aw/awscli/package.nix
index 311201f73d07..39cc67df9f87 100644
--- a/pkgs/by-name/aw/awscli/package.nix
+++ b/pkgs/by-name/aw/awscli/package.nix
@@ -14,14 +14,14 @@ let
     pname = "awscli";
     # N.B: if you change this, change botocore and boto3 to a matching version too
     # check e.g. https://github.com/aws/aws-cli/blob/1.33.21/setup.py
-    version = "1.40.8";
+    version = "1.40.31";
     pyproject = true;
 
     src = fetchFromGitHub {
       owner = "aws";
       repo = "aws-cli";
       tag = version;
-      hash = "sha256-gldyfko4yrpq/U8w87qxRzqXEfUxfCTEjsRO8bPJOAc=";
+      hash = "sha256-BjQyA7uK9F/5myPXsMpD0HZK69Se3WveYMHNCzhVNKc=";
     };
 
     pythonRelaxDeps = [
diff --git a/pkgs/by-name/aw/awscli2/package.nix b/pkgs/by-name/aw/awscli2/package.nix
index 068d6790304c..763e992b5594 100644
--- a/pkgs/by-name/aw/awscli2/package.nix
+++ b/pkgs/by-name/aw/awscli2/package.nix
@@ -23,11 +23,11 @@ let
             "test_check_link_response_only" # fails on hydra https://hydra.nixos.org/build/242624087/nixlog/1
           ];
         });
-        python-dateutil = prev.python-dateutil.overridePythonAttrs (prev: {
+        python-dateutil = prev.python-dateutil.overridePythonAttrs (prev: rec {
           version = "2.8.2";
           pyproject = null;
           src = prev.src.override {
-            version = "2.8.2";
+            inherit version;
             hash = "sha256-ASPKzBYnrhnd88J6XeW9Z+5FhvvdZEDZdI+Ku0g9PoY=";
           };
           patches = [
@@ -40,16 +40,16 @@ let
           ];
           postPatch = null;
         });
-        ruamel-yaml = prev.ruamel-yaml.overridePythonAttrs (prev: {
+        ruamel-yaml = prev.ruamel-yaml.overridePythonAttrs (prev: rec {
+          version = "0.17.21";
           src = prev.src.override {
-            version = "0.17.21";
+            inherit version;
             hash = "sha256-i3zml6LyEnUqNcGsQURx3BbEJMlXO+SSa1b/P10jt68=";
           };
         });
         urllib3 = prev.urllib3.overridePythonAttrs (prev: rec {
-          pyproject = true;
           version = "1.26.18";
-          nativeBuildInputs = with final; [
+          build-system = with final; [
             setuptools
           ];
           src = prev.src.override {
@@ -64,21 +64,20 @@ let
 in
 py.pkgs.buildPythonApplication rec {
   pname = "awscli2";
-  version = "2.27.8"; # N.B: if you change this, check if overrides are still up-to-date
+  version = "2.27.31"; # N.B: if you change this, check if overrides are still up-to-date
   pyproject = true;
 
   src = fetchFromGitHub {
     owner = "aws";
     repo = "aws-cli";
     tag = version;
-    hash = "sha256-AluBRKB5HKK+8Pb2UooUWqrE48ZNGffkW1z3mLHzVRg=";
+    hash = "sha256-0d7VdlX3xZkw1SVjbKErFhhoC2owI/JfBQOJ/GfIWyg=";
   };
 
   postPatch = ''
     substituteInPlace pyproject.toml \
       --replace-fail 'flit_core>=3.7.1,<3.9.1' 'flit_core>=3.7.1' \
       --replace-fail 'awscrt==' 'awscrt>=' \
-      --replace-fail 'cryptography>=40.0.0,<43.0.2' 'cryptography>=43.0.0' \
       --replace-fail 'distro>=1.5.0,<1.9.0' 'distro>=1.5.0' \
       --replace-fail 'docutils>=0.10,<0.20' 'docutils>=0.10' \
       --replace-fail 'prompt-toolkit>=3.0.24,<3.0.39' 'prompt-toolkit>=3.0.24' \
@@ -103,19 +102,14 @@ py.pkgs.buildPythonApplication rec {
 
   dependencies = with py.pkgs; [
     awscrt
-    bcdoc
-    botocore
     colorama
-    cryptography
     distro
     docutils
     jmespath
     prompt-toolkit
     python-dateutil
-    pyyaml
     ruamel-yaml
     urllib3
-    zipp
   ];
 
   propagatedBuildInputs = [
diff --git a/pkgs/development/python-modules/boto3/default.nix b/pkgs/development/python-modules/boto3/default.nix
index 5d58a7171c12..39b5dd0c3cad 100644
--- a/pkgs/development/python-modules/boto3/default.nix
+++ b/pkgs/development/python-modules/boto3/default.nix
@@ -25,7 +25,7 @@ buildPythonPackage rec {
     owner = "boto";
     repo = "boto3";
     tag = version;
-    hash = "sha256-OYD/PC/UO6jqBBlMwXJE+5kdIIX72C1Bpz4iswmQ/IA=";
+    hash = "sha256-3NK9xp58w+Wrhs/i7eXLF/P9Dwadptrr4LlpV6MRbGM=";
   };
 
   build-system = [
diff --git a/pkgs/development/python-modules/botocore/default.nix b/pkgs/development/python-modules/botocore/default.nix
index 2fb38ef93148..742b4bc893d8 100644
--- a/pkgs/development/python-modules/botocore/default.nix
+++ b/pkgs/development/python-modules/botocore/default.nix
@@ -19,14 +19,14 @@
 
 buildPythonPackage rec {
   pname = "botocore";
-  version = "1.38.9"; # N.B: if you change this, change boto3 and awscli to a matching version
+  version = "1.38.32"; # N.B: if you change this, change boto3 and awscli to a matching version
   pyproject = true;
 
   src = fetchFromGitHub {
     owner = "boto";
     repo = "botocore";
     tag = version;
-    hash = "sha256-rFLnSM7SwzXS08+Qde2FqU+sP5SIVAawP34iG8keAtM=";
+    hash = "sha256-KW9EAeunL3+pccGsrFitonc5EHdm2Cd+7dM3kdvdkvM=";
   };
 
   build-system = [
diff --git a/pkgs/development/python-modules/prompt-toolkit/default.nix b/pkgs/development/python-modules/prompt-toolkit/default.nix
index d468634e5be5..415d869aa48a 100644
--- a/pkgs/development/python-modules/prompt-toolkit/default.nix
+++ b/pkgs/development/python-modules/prompt-toolkit/default.nix
@@ -18,6 +18,12 @@ buildPythonPackage rec {
     hash = "sha256-kxoWLjsn/JDIbxtIux+yxSjCdhR15XycBt4TMRx7VO0=";
   };
 
+  postPatch = ''
+    # https://github.com/prompt-toolkit/python-prompt-toolkit/issues/1988
+    substituteInPlace src/prompt_toolkit/__init__.py \
+      --replace-fail 'metadata.version("prompt_toolkit")' '"${version}"'
+  '';
+
   build-system = [ setuptools ];
 
   dependencies = [ wcwidth ];
diff --git a/pkgs/development/python-modules/s3transfer/default.nix b/pkgs/development/python-modules/s3transfer/default.nix
index 358fee1ad867..24a24150b11f 100644
--- a/pkgs/development/python-modules/s3transfer/default.nix
+++ b/pkgs/development/python-modules/s3transfer/default.nix
@@ -10,14 +10,14 @@
 
 buildPythonPackage rec {
   pname = "s3transfer";
-  version = "0.12.0";
+  version = "0.13.0";
   pyproject = true;
 
   src = fetchFromGitHub {
     owner = "boto";
     repo = "s3transfer";
     tag = version;
-    hash = "sha256-CCsZUQHP/DsRozynbDeVOuAXjRAy+klaPGVJY3h/FAs=";
+    hash = "sha256-Ou3U7IPGJdK9exOLMgPFoTbOQi9IA+ivoGVOygB4ACE=";
   };
 
   build-system = [