diff --git a/apple/scripts/release/notarize.sh b/apple/scripts/release/notarize.sh
index 17a89287e7..f7146efc34 100755
--- a/apple/scripts/release/notarize.sh
+++ b/apple/scripts/release/notarize.sh
@@ -18,6 +18,26 @@ die() {
     exit 1
 }
 
+# CloudKit, where stapler looks the ticket up, can lag notarytool's Accepted; 65 and 68 are failed lookups.
+staple() {
+    local path="$1" name attempt status delay
+    name="$(basename "$path")"
+    for attempt in 1 2 3; do
+        status=0
+        xcrun stapler staple "$path" || status=$?
+        case "$status" in
+            0) return 0 ;;
+            65 | 68) ;;
+            *) die "stapling $name failed (stapler exit $status)" ;;
+        esac
+        [ "$attempt" -lt 3 ] || break
+        delay=$((attempt * 30))
+        echo "Stapling $name: no ticket yet (stapler exit $status, attempt $attempt of 3), retrying in ${delay}s"
+        sleep "$delay"
+    done
+    die "stapling $name failed after 3 attempts (stapler exit $status)"
+}
+
 [ $# -gt 0 ] || usage
 WORK="$(mktemp -d)"
 trap 'rm -rf "$WORK"' EXIT
@@ -63,7 +83,7 @@ fi
 
 for path in "${PATHS[@]}"; do
     name="$(basename "$path")"
-    xcrun stapler staple "$path" || die "stapling $name failed"
+    staple "$path"
     case "$path" in
         *.app) assessment=(-t exec) ;;
         *) assessment=(-t open --context context:primary-signature) ;;
diff --git a/apple/scripts/release/test_notarize.py b/apple/scripts/release/test_notarize.py
new file mode 100644
index 0000000000..e66137c3d1
--- /dev/null
+++ b/apple/scripts/release/test_notarize.py
@@ -0,0 +1,114 @@
+#!/usr/bin/env python3
+
+import os
+import subprocess
+import tempfile
+import unittest
+from pathlib import Path
+
+SCRIPT = Path(__file__).resolve().parent / "notarize.sh"
+
+STUBS = {
+    "xcrun": r"""#!/usr/bin/env bash
+set -euo pipefail
+case "$1 $2" in
+    "notarytool submit") echo '{"status":"Accepted","id":"stub-id","message":"Processing complete"}' ;;
+    "notarytool log") echo '{}' ;;
+    "stapler staple")
+        name="$(basename "$3")"
+        echo "staple $name" >> "$STUB_STATE/calls"
+        codes="$STUB_STATE/staple-$name"
+        [ -s "$codes" ] || exit 0
+        code="$(head -n 1 "$codes")"
+        tail -n +2 "$codes" > "$codes.rest"
+        mv "$codes.rest" "$codes"
+        exit "$code"
+        ;;
+    *) echo "stub xcrun: unexpected $*" >&2; exit 99 ;;
+esac
+""",
+    "plutil": r"""#!/usr/bin/env bash
+set -euo pipefail
+sed -n "s/.*\"$2\":\"\([^\"]*\)\".*/\1/p" "$6"
+""",
+    "ditto": r"""#!/usr/bin/env bash
+set -euo pipefail
+if [ "$1" = "-c" ]; then
+    for last; do :; done
+    : > "$last"
+else
+    cp -R "$1" "$2"
+fi
+""",
+    "spctl": """#!/usr/bin/env bash
+echo "source=Notarized Developer ID"
+""",
+    "sleep": """#!/usr/bin/env bash
+echo "sleep $1" >> "$STUB_STATE/calls"
+""",
+}
+
+
+class StapleTests(unittest.TestCase):
+    def setUp(self):
+        directory = tempfile.TemporaryDirectory()
+        self.addCleanup(directory.cleanup)
+        self.root = Path(directory.name)
+        self.bin = self.root / "bin"
+        self.state = self.root / "state"
+        self.bin.mkdir()
+        self.state.mkdir()
+        for name, body in STUBS.items():
+            stub = self.bin / name
+            stub.write_text(body, encoding="utf-8")
+            stub.chmod(0o755)
+
+    def bundle(self, name, staple_exits=()):
+        path = self.root / name
+        path.mkdir()
+        (self.state / f"staple-{name}").write_text("".join(f"{code}\n" for code in staple_exits), encoding="utf-8")
+        return path
+
+    def notarize(self, *paths):
+        env = {**os.environ, "PATH": f"{self.bin}{os.pathsep}{os.environ['PATH']}", "STUB_STATE": str(self.state)}
+        return subprocess.run(["bash", str(SCRIPT), *map(str, paths)], env=env, capture_output=True, text=True)
+
+    def calls(self):
+        calls = self.state / "calls"
+        return calls.read_text(encoding="utf-8").splitlines() if calls.exists() else []
+
+    def test_a_late_ticket_is_stapled_on_a_retry(self):
+        late = self.bundle("Late.tableplugin", [65, 68])
+        ready = self.bundle("Ready.tableplugin")
+        result = self.notarize(late, ready)
+        self.assertEqual(result.returncode, 0, result.stderr)
+        self.assertEqual(self.calls(), [
+            "staple Late.tableplugin", "sleep 30",
+            "staple Late.tableplugin", "sleep 60",
+            "staple Late.tableplugin",
+            "staple Ready.tableplugin",
+        ])
+        self.assertEqual(result.stdout.count("Stapling Late.tableplugin: no ticket yet"), 2)
+        self.assertIn("Ready.tableplugin: notarized, stapled and accepted by Gatekeeper", result.stdout)
+
+    def test_a_ticket_missing_after_three_attempts_fails(self):
+        missing = self.bundle("Missing.tableplugin", [65, 65, 65])
+        result = self.notarize(missing)
+        self.assertEqual(result.returncode, 1)
+        self.assertEqual(self.calls(), [
+            "staple Missing.tableplugin", "sleep 30",
+            "staple Missing.tableplugin", "sleep 60",
+            "staple Missing.tableplugin",
+        ])
+        self.assertIn("stapling Missing.tableplugin failed after 3 attempts (stapler exit 65)", result.stderr)
+
+    def test_any_other_stapler_failure_is_final(self):
+        unsigned = self.bundle("Unsigned.tableplugin", [66])
+        result = self.notarize(unsigned)
+        self.assertEqual(result.returncode, 1)
+        self.assertEqual(self.calls(), ["staple Unsigned.tableplugin"])
+        self.assertIn("stapling Unsigned.tableplugin failed (stapler exit 66)", result.stderr)
+
+
+if __name__ == "__main__":
+    unittest.main()