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diff --git a/.ai/scripts/upcoming_birthdays.py b/.ai/scripts/upcoming_birthdays.py
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+#!/usr/bin/env python3
+"""Upcoming-birthdays block for daily prep.
+
+Reads an org-contacts file for ``:BIRTHDAY: YYYY-MM-DD`` properties, finds the
+ones whose next occurrence falls within a window (default 30 days) from today,
+and prints a daily-prep block: name, date, days-away, and — when the birth year
+is real — the age the person is turning. Many contacts use ``1900`` as a
+placeholder year when the real one is unknown; those render date-only, no age.
+Anything within the callout window (default 7 days) is flagged so a gift or
+plan gets prompted.
+
+Pure core:
+  parse_birthdays(text) -> [Birthday(name, month, day, year|None), ...]
+  upcoming(birthdays, today, window=30) -> [Upcoming(name, date, days_away, age|None), ...]
+  format_block(items, window, callout_days=7) -> str
+
+CLI:
+  upcoming_birthdays.py [--file PATH] [--today YYYY-MM-DD] [--window N] [--callout N]
+prints the block on stdout. Default --file is ~/sync/org/contacts.org.
+"""
+
+import argparse
+import datetime as dt
+import re
+import sys
+from dataclasses import dataclass
+from pathlib import Path
+
+PLACEHOLDER_YEAR = 1900
+DEFAULT_CONTACTS = Path.home() / "sync" / "org" / "contacts.org"
+
+_HEADING_RE = re.compile(r"^\*+\s+(.*?)\s*$")
+_TAGS_RE = re.compile(r"\s+:[A-Za-z0-9_@#%:]+:$")
+_BIRTHDAY_RE = re.compile(r"^\s*:BIRTHDAY:\s*(\d{4})-(\d{2})-(\d{2})\s*$")
+
+
+@dataclass(frozen=True)
+class Birthday:
+    name: str
+    month: int
+    day: int
+    year: int | None  # None when the source used the 1900 placeholder
+
+
+@dataclass(frozen=True)
+class Upcoming:
+    name: str
+    date: dt.date
+    days_away: int
+    age: int | None  # None when the birth year is unknown
+
+
+def _clean_name(heading_text: str) -> str:
+    """Strip a trailing org tag cluster from a heading's text."""
+    return _TAGS_RE.sub("", heading_text).strip()
+
+
+def parse_birthdays(text: str) -> list[Birthday]:
+    """Extract (name, month, day, year|None) for every contact with a BIRTHDAY.
+
+    The name is the nearest preceding org heading. A birth year of 1900 is the
+    placeholder org-contacts uses for an unknown year and is returned as None.
+    Malformed birthday lines are ignored.
+    """
+    birthdays: list[Birthday] = []
+    current_name: str | None = None
+    for line in text.splitlines():
+        heading = _HEADING_RE.match(line)
+        if heading:
+            current_name = _clean_name(heading.group(1))
+            continue
+        bday = _BIRTHDAY_RE.match(line)
+        if bday and current_name:
+            year, month, day = (int(g) for g in bday.groups())
+            # Guard against a nonsense month/day that regex width still admits.
+            try:
+                dt.date(2000, month, day)
+            except ValueError:
+                continue
+            birthdays.append(
+                Birthday(
+                    current_name,
+                    month,
+                    day,
+                    None if year == PLACEHOLDER_YEAR else year,
+                )
+            )
+    return birthdays
+
+
+def _next_occurrence(month: int, day: int, today: dt.date) -> dt.date:
+    """First date on/after ``today`` landing on this month/day.
+
+    A Feb 29 birthday maps to Feb 28 in a non-leap year.
+    """
+    def on(year: int) -> dt.date:
+        try:
+            return dt.date(year, month, day)
+        except ValueError:
+            # Only Feb 29 can fail here; fall back to Feb 28.
+            return dt.date(year, 2, 28)
+
+    candidate = on(today.year)
+    if candidate < today:
+        candidate = on(today.year + 1)
+    return candidate
+
+
+def upcoming(
+    birthdays: list[Birthday], today: dt.date, window: int = 30
+) -> list[Upcoming]:
+    """Birthdays whose next occurrence is within ``window`` days, soonest first."""
+    items: list[Upcoming] = []
+    for b in birthdays:
+        occ = _next_occurrence(b.month, b.day, today)
+        days = (occ - today).days
+        if 0 <= days <= window:
+            age = None if b.year is None else occ.year - b.year
+            items.append(Upcoming(b.name, occ, days, age))
+    items.sort(key=lambda u: (u.days_away, u.name))
+    return items
+
+
+def _days_phrase(days: int) -> str:
+    if days == 0:
+        return "today"
+    if days == 1:
+        return "tomorrow"
+    return f"in {days} days"
+
+
+def format_block(items: list[Upcoming], window: int, callout_days: int = 7) -> str:
+    """Render the daily-prep block. Callout entries (within ``callout_days``) are
+    flagged with a marker and a plan-a-gift nudge."""
+    if not items:
+        return f"No birthdays in the next {window} days."
+
+    lines = [f"Upcoming birthdays (next {window} days):"]
+    for u in items:
+        callout = u.days_away <= callout_days
+        marker = "⚠" if callout else "·"
+        date_str = u.date.strftime("%a %b %d")
+        piece = f"  {marker} {date_str} — {u.name}"
+        if u.age is not None:
+            piece += f" turns {u.age}"
+        piece += f" ({_days_phrase(u.days_away)})"
+        if callout:
+            piece += " — plan a gift/card"
+        lines.append(piece)
+    return "\n".join(lines)
+
+
+def _parse_today(value: str | None) -> dt.date:
+    if value is None:
+        return dt.date.today()
+    return dt.date.fromisoformat(value)
+
+
+def main(argv: list[str] | None = None) -> int:
+    parser = argparse.ArgumentParser(description="Print the upcoming-birthdays daily-prep block.")
+    parser.add_argument("--file", type=Path, default=DEFAULT_CONTACTS,
+                        help="org-contacts file (default: ~/sync/org/contacts.org)")
+    parser.add_argument("--today", default=None,
+                        help="override today's date (YYYY-MM-DD), for testing")
+    parser.add_argument("--window", type=int, default=30,
+                        help="look-ahead window in days (default: 30)")
+    parser.add_argument("--callout", type=int, default=7,
+                        help="flag birthdays within this many days (default: 7)")
+    args = parser.parse_args(argv)
+
+    if not args.file.exists():
+        print(f"contacts file not found: {args.file}", file=sys.stderr)
+        return 1
+
+    text = args.file.read_text(encoding="utf-8")
+    items = upcoming(parse_birthdays(text), _parse_today(args.today), args.window)
+    print(format_block(items, args.window, args.callout))
+    return 0
+
+
+if __name__ == "__main__":
+    raise SystemExit(main())