From 45d95f1107014c81a3a49c3bc760bda3d90050f7 Mon Sep 17 00:00:00 2001
From: Brandon Thomas <brandon@storyteller.ai>
Date: Wed, 28 Oct 2026 12:09:18 -0400
Subject: [PATCH] macOS packaging: retry stapler when Apple's CloudKit drops
 the connection

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
---
 packaging/macos/package.sh | 23 +++++++++++++++++++----
 1 file changed, 19 insertions(+), 4 deletions(-)

diff --git a/packaging/macos/package.sh b/packaging/macos/package.sh
index 50701e0c1..ef1b7f6c7 100755
--- a/packaging/macos/package.sh
+++ b/packaging/macos/package.sh
@@ -80,6 +80,21 @@ sign() {
   codesign --force --sign "$IDENTITY" ${kc[@]+"${kc[@]}"} "${ts[@]}" "$@"
 }
 
+# `stapler staple` and `stapler validate` both fetch the ticket from Apple's CloudKit, and a dropped
+# connection there (NSURLErrorDomain -1005, "Error 68") fails them although notarization worked.
+# Both are idempotent, so retry with a pause; a missing or bad ticket still fails every try.
+stapler_retry() {
+  local try
+  for try in 1 2 3 4; do
+    xcrun stapler "$1" "$2" && return 0
+    [[ "$try" = 4 ]] && break
+    echo "stapler $1 failed (try $try of 4); retrying in $((try * 20)) s" >&2
+    sleep $((try * 20))
+  done
+  echo "error: stapler $1 $(basename "$2") failed 4 times" >&2
+  exit 1
+}
+
 notarize() {
   local file="$1" out id status
   echo "==> notarizing $(basename "$file") (this can take a few minutes)"
@@ -127,8 +142,8 @@ codesign --verify --strict --deep --verbose=2 "$APP"
 if [[ "$NOTARIZE" = 1 ]]; then
   ditto -c -k --keepParent "$APP" "$WORK/PdfCraft-notarize.zip"
   notarize "$WORK/PdfCraft-notarize.zip"
-  xcrun stapler staple "$APP"
-  xcrun stapler validate "$APP"
+  stapler_retry staple "$APP"
+  stapler_retry validate "$APP"
   spctl --assess --type execute -vvv "$APP"
 fi
 
@@ -178,8 +193,8 @@ fi
 hdiutil_retry detach detach "$MOUNT" >/dev/null
 if [[ "$NOTARIZE" = 1 ]]; then
   notarize "$DMG"
-  xcrun stapler staple "$DMG"
-  xcrun stapler validate "$DMG"
+  stapler_retry staple "$DMG"
+  stapler_retry validate "$DMG"
   spctl --assess --type open --context context:primary-signature -vvv "$DMG"
 fi