diff --git a/pkgs/development/python-modules/pyscard/default.nix b/pkgs/development/python-modules/pyscard/default.nix
index bee5d760c0c6..0a98ee02e581 100644
--- a/pkgs/development/python-modules/pyscard/default.nix
+++ b/pkgs/development/python-modules/pyscard/default.nix
@@ -1,4 +1,4 @@
-{ stdenv, fetchurl, buildPythonPackage, swig, pcsclite }:
+{ stdenv, fetchurl, buildPythonPackage, swig, pcsclite, PCSC }:
 
 buildPythonPackage rec {
   version = "1.9.6";
@@ -18,7 +18,7 @@ buildPythonPackage rec {
   NIX_CFLAGS_COMPILE = "-isystem ${pcsclite}/include/PCSC/";
 
   propagatedBuildInputs = [ pcsclite ];
-  buildInputs = [ swig ];
+  buildInputs = [ swig ] ++ stdenv.lib.optional stdenv.isDarwin PCSC;
 
   meta = {
     homepage = https://pyscard.sourceforge.io/;
diff --git a/pkgs/tools/misc/yubikey-manager/default.nix b/pkgs/tools/misc/yubikey-manager/default.nix
index 820f193e5e25..c7fbeddd13a4 100644
--- a/pkgs/tools/misc/yubikey-manager/default.nix
+++ b/pkgs/tools/misc/yubikey-manager/default.nix
@@ -2,11 +2,11 @@
   yubikey-personalization, libu2f-host, libusb1 }:
 
 pythonPackages.buildPythonPackage rec {
-  name = "yubikey-manager-0.3.1";
+  name = "yubikey-manager-0.4.0";
 
   srcs = fetchurl {
     url = "https://developers.yubico.com/yubikey-manager/Releases/${name}.tar.gz";
-    sha256 = "0vrhaqb8yc1qjq25k9dv8gmqxhbf6aa047i6dvz1lcraq6zwnq6g";
+    sha256 = "0dc0mqg8r6kjh0s2rmrggfxbx9imslajjrj80rffcvg64a2vgsgb";
   };
 
   propagatedBuildInputs =
@@ -16,6 +16,7 @@ pythonPackages.buildPythonPackage rec {
       cryptography
       pyscard
       pyusb
+      pyopenssl
       six
     ] ++ [
       libu2f-host
@@ -32,6 +33,9 @@ pythonPackages.buildPythonPackage rec {
     _YKMAN_COMPLETE=source $out/bin/ykman > $out/etc/bash_completion.d/ykman.sh ||true
   '';
 
+  # See https://github.com/NixOS/nixpkgs/issues/29169
+  doCheck = false;
+
   meta = with lib; {
     homepage = https://developers.yubico.com/yubikey-manager;
     description = "Command line tool for configuring any YubiKey over all USB transports.";
diff --git a/pkgs/top-level/python-packages.nix b/pkgs/top-level/python-packages.nix
index 55a096dbec30..68948a5be9d4 100644
--- a/pkgs/top-level/python-packages.nix
+++ b/pkgs/top-level/python-packages.nix
@@ -259,7 +259,7 @@ in {
     pythonPackages = self;
   };
 
-  pyscard = callPackage ../development/python-modules/pyscard { };
+  pyscard = callPackage ../development/python-modules/pyscard { inherit (pkgs.darwin.apple_sdk.frameworks) PCSC; };
 
   pyside = callPackage ../development/python-modules/pyside { };
 
@@ -24234,11 +24234,15 @@ EOF
     };
 
     # Fix the USB backend library lookup
-    postPatch = ''
-      libusb=${pkgs.libusb1.out}/lib/libusb-1.0.so
-      test -f $libusb || { echo "ERROR: $libusb doesn't exist, please update/fix this build expression."; exit 1; }
-      sed -i -e "s|find_library=None|find_library=lambda _:\"$libusb\"|" usb/backend/libusb1.py
-    '';
+    postPatch =
+      let
+        # This should really be in the stdenv somewhere
+        soext = if stdenv.isLinux then "so" else if stdenv.isDarwin then "dylib" else throw "Unsupported platform";
+      in ''
+        libusb=${pkgs.libusb1.out}/lib/libusb-1.0.${soext}
+        test -f $libusb || { echo "ERROR: $libusb doesn't exist, please update/fix this build expression."; exit 1; }
+        sed -i -e "s|find_library=None|find_library=lambda _:\"$libusb\"|" usb/backend/libusb1.py
+      '';
 
     propagatedBuildInputs = [ pkgs.libusb ];