diff --git a/.editorconfig b/.editorconfig
index 3c7962ab4d8b..a4f216d71a22 100644
--- a/.editorconfig
+++ b/.editorconfig
@@ -60,6 +60,13 @@ indent_size = unset
 [*.md]
 trim_trailing_whitespace = unset
 
+# binaries
+[*.nib]
+end_of_line = unset
+insert_final_newline = unset
+trim_trailing_whitespace = unset
+charset = unset
+
 [eggs.nix]
 trim_trailing_whitespace = unset
 
diff --git a/pkgs/tools/security/pinentry/mac.nix b/pkgs/tools/security/pinentry/mac.nix
index 27917ffbbf17..daf2d82d66b0 100644
--- a/pkgs/tools/security/pinentry/mac.nix
+++ b/pkgs/tools/security/pinentry/mac.nix
@@ -1,32 +1,78 @@
-{ lib, stdenv, fetchFromGitHub, xcbuildHook, libiconv, ncurses, Cocoa }:
+{ lib
+, stdenv
+, fetchFromGitHub
+, autoreconfHook
+, libassuan
+, libgpg-error
+, libiconv
+, texinfo
+, common-updater-scripts
+, writers
+, Cocoa
+}:
 
-stdenv.mkDerivation {
+stdenv.mkDerivation rec {
   pname = "pinentry-mac";
-  version = "0.9.4";
+
+  # NOTE: Don't update manually. Use passthru.updateScript on a Mac with XCode
+  # installed.
+  version = "1.1.1.1";
 
   src = fetchFromGitHub {
-    owner = "matthewbauer";
-    repo = "pinentry-mac";
-    rev = "6dfef256c8ea32d642fea847f27d800f024cf51e";
-    sha256 = "0g75302697gqcxyf2hyqzvcbd5pyss1bl2xvfd40wqav7dlyvj83";
+    owner = "GPGTools";
+    repo = "pinentry";
+    rev = "v${version}";
+    sha256 = "sha256-QnDuqFrI/U7aZ5WcOCp5vLE+w59LVvDGOFNQy9fSy70=";
   };
 
-  nativeBuildInputs = [ xcbuildHook ];
-  buildInputs = [ libiconv ncurses Cocoa ];
-
-  preBuild = ''
-    # Only build for what we care about (also allows arm64)
-    substituteInPlace pinentry-mac.xcodeproj/project.pbxproj \
-      --replace "i386 x86_64 ppc" "${stdenv.targetPlatform.darwinArch}"
+  # use pregenerated nib files because generating them requires XCode
+  postPatch = ''
+    cp -r ${./mac/Main.nib} macosx/Main.nib
+    cp -r ${./mac/Pinentry.nib} macosx/Pinentry.nib
+    chmod -R u+w macosx/*.nib
   '';
 
+  nativeBuildInputs = [ autoreconfHook texinfo ];
+  buildInputs = [ libassuan libgpg-error libiconv Cocoa ];
+
+  configureFlags = [ "--enable-maintainer-mode" "--disable-ncurses" ];
+
   installPhase = ''
     mkdir -p $out/Applications
-    mv Products/Release/pinentry-mac.app $out/Applications
+    mv macosx/pinentry-mac.app $out/Applications
   '';
 
+  enableParallelBuilding = true;
+
   passthru = {
     binaryPath = "Applications/pinentry-mac.app/Contents/MacOS/pinentry-mac";
+    updateScript = writers.writeBash "update-pinentry-mac" ''
+      set -euxo pipefail
+
+      main() {
+        tag="$(queryLatestTag)"
+        ver="$(expr "$tag" : 'v\(.*\)')"
+
+        ${common-updater-scripts}/bin/update-source-version pinentry_mac "$ver"
+
+        cd ${lib.escapeShellArg ./.}
+        rm -rf mac
+        mkdir mac
+
+        srcDir="$(nix-build ../../../.. --no-out-link -A pinentry_mac.src)"
+        for path in "$srcDir"/macosx/*.xib; do
+          filename="''${path##*/}"
+          /usr/bin/ibtool --compile "mac/''${filename%.*}.nib" "$path"
+        done
+      }
+
+      queryLatestTag() {
+        curl -sS https://api.github.com/repos/GPGTools/pinentry/tags \
+          | jq -r '.[] | .name' | sort --version-sort | tail -1
+      }
+
+      main
+    '';
   };
 
   meta = {
diff --git a/pkgs/tools/security/pinentry/mac/Main.nib/keyedobjects-101300.nib b/pkgs/tools/security/pinentry/mac/Main.nib/keyedobjects-101300.nib
new file mode 100644
index 000000000000..18cc1c8b46f5
Binary files /dev/null and b/pkgs/tools/security/pinentry/mac/Main.nib/keyedobjects-101300.nib differ
diff --git a/pkgs/tools/security/pinentry/mac/Main.nib/keyedobjects.nib b/pkgs/tools/security/pinentry/mac/Main.nib/keyedobjects.nib
new file mode 100644
index 000000000000..90635122ffdc
Binary files /dev/null and b/pkgs/tools/security/pinentry/mac/Main.nib/keyedobjects.nib differ
diff --git a/pkgs/tools/security/pinentry/mac/Pinentry.nib/keyedobjects-101300.nib b/pkgs/tools/security/pinentry/mac/Pinentry.nib/keyedobjects-101300.nib
new file mode 100644
index 000000000000..6df3d5f46227
Binary files /dev/null and b/pkgs/tools/security/pinentry/mac/Pinentry.nib/keyedobjects-101300.nib differ
diff --git a/pkgs/tools/security/pinentry/mac/Pinentry.nib/keyedobjects.nib b/pkgs/tools/security/pinentry/mac/Pinentry.nib/keyedobjects.nib
new file mode 100644
index 000000000000..aa8bca0d085e
Binary files /dev/null and b/pkgs/tools/security/pinentry/mac/Pinentry.nib/keyedobjects.nib differ
diff --git a/pkgs/top-level/all-packages.nix b/pkgs/top-level/all-packages.nix
index b6ff5da1d143..fdb78390032d 100644
--- a/pkgs/top-level/all-packages.nix
+++ b/pkgs/top-level/all-packages.nix
@@ -9830,7 +9830,6 @@ with pkgs;
 
   pinentry_mac = callPackage ../tools/security/pinentry/mac.nix {
     inherit (darwin.apple_sdk.frameworks) Cocoa;
-    xcbuildHook = if stdenv.targetPlatform.isAarch64 then xcbuildHook else xcbuild6Hook;
   };
 
   pinentry-bemenu = callPackage ../tools/security/pinentry-bemenu { };