diff --git a/apps/bot/src/reminders/time-parsing.ts b/apps/bot/src/reminders/time-parsing.ts
index 825d89c..cb1220b 100644
--- a/apps/bot/src/reminders/time-parsing.ts
+++ b/apps/bot/src/reminders/time-parsing.ts
@@ -75,6 +75,35 @@ export function parseTypedDate(
   return { ok: true, dayOffset: diffDays, label: targetDay.toFormat("EEE dd MMM yyyy") };
 }
 
+/** Compute the day-offset from "today" in the given timezone for a year/month/day. */
+export function dayOffsetFromYMD(
+  year: number,
+  month: number,
+  day: number,
+  timezone: string = DEFAULT_TIMEZONE,
+): { ok: true; dayOffset: number; label: string } | { ok: false; reason: string } {
+  const target = DateTime.fromObject({ year, month, day }, { zone: timezone });
+  if (!target.isValid) {
+    return { ok: false, reason: "Invalid date" };
+  }
+  const today = DateTime.now().setZone(timezone).startOf("day");
+  const diffDays = Math.round(target.startOf("day").diff(today, "days").days);
+  if (diffDays < 0) {
+    return { ok: false, reason: "That date is in the past" };
+  }
+  return { ok: true, dayOffset: diffDays, label: target.toFormat("EEE dd MMM yyyy") };
+}
+
+/** Today's year/month/day in a given timezone. Used by the calendar picker. */
+export function todayYMD(timezone: string = DEFAULT_TIMEZONE): {
+  year: number;
+  month: number;
+  day: number;
+} {
+  const now = DateTime.now().setZone(timezone);
+  return { year: now.year, month: now.month, day: now.day };
+}
+
 export type ParseResult = { ok: true; date: Date } | { ok: false; reason: string };
 
 const FORMATS = [
diff --git a/apps/bot/src/telegram/bot.ts b/apps/bot/src/telegram/bot.ts
index 0905d82..61ba07c 100644
--- a/apps/bot/src/telegram/bot.ts
+++ b/apps/bot/src/telegram/bot.ts
@@ -36,7 +36,11 @@ import {
   wizardPickDay,
   wizardPickHour,
   wizardPickMinute,
-  wizardTypeDatePrompt,
+  wizardPickYearStart,
+  wizardPickYear,
+  wizardPickMonth,
+  wizardPickDayOfMonth,
+  wizardNoop,
 } from "./callbacks.js";
 import {
   consumePendingPairLabel,
@@ -132,10 +136,25 @@ export function createTelegramBot(): Bot {
       await wizardSetTimeQuick(ctx, choice as Quick);
     }
   });
-  bot.callbackQuery("rmd:type", wizardTypeDatePrompt);
+  bot.callbackQuery("rmd:exact", wizardPickYearStart);
+  bot.callbackQuery("rm_noop", wizardNoop);
   bot.callbackQuery(/^rmd:(\d+)$/, async (ctx) => {
     await wizardPickDay(ctx, Number(ctx.match[1]));
   });
+  bot.callbackQuery(/^rmy:(\d+)$/, async (ctx) => {
+    await wizardPickYear(ctx, Number(ctx.match[1]));
+  });
+  bot.callbackQuery(/^rmM:(\d+):(\d+)$/, async (ctx) => {
+    await wizardPickMonth(ctx, Number(ctx.match[1]), Number(ctx.match[2]));
+  });
+  bot.callbackQuery(/^rmD:(\d+):(\d+):(\d+)$/, async (ctx) => {
+    await wizardPickDayOfMonth(
+      ctx,
+      Number(ctx.match[1]),
+      Number(ctx.match[2]),
+      Number(ctx.match[3]),
+    );
+  });
   bot.callbackQuery(/^rmh:(\d+):(\d+)$/, async (ctx) => {
     await wizardPickHour(ctx, Number(ctx.match[1]), Number(ctx.match[2]));
   });
diff --git a/apps/bot/src/telegram/callbacks.ts b/apps/bot/src/telegram/callbacks.ts
index 4e9c9c9..a02f473 100644
--- a/apps/bot/src/telegram/callbacks.ts
+++ b/apps/bot/src/telegram/callbacks.ts
@@ -399,13 +399,67 @@ export async function wizardPickDay(ctx: Context, dayOffset: number): Promise<vo
   await showMenu(ctx, reminderPickHourMenu(formatCustomDay(dayOffset, tz), dayOffset));
 }
 
-export async function wizardTypeDatePrompt(ctx: Context): Promise<void> {
+export async function wizardPickYearStart(ctx: Context): Promise<void> {
+  await ctx.answerCallbackQuery();
+  const op = await findOperator(ctx);
+  const tz = op?.defaultTimezone ?? DEFAULT_TIMEZONE;
+  const { todayYMD } = await import("../reminders/time-parsing.js");
+  const { reminderPickYearMenu } = await import("./menus.js");
+  await showMenu(ctx, reminderPickYearMenu(todayYMD(tz).year));
+}
+
+export async function wizardPickYear(ctx: Context, year: number): Promise<void> {
+  await ctx.answerCallbackQuery();
+  const op = await findOperator(ctx);
+  const tz = op?.defaultTimezone ?? DEFAULT_TIMEZONE;
+  const { todayYMD } = await import("../reminders/time-parsing.js");
+  const { reminderPickMonthMenu } = await import("./menus.js");
+  const today = todayYMD(tz);
+  await showMenu(ctx, reminderPickMonthMenu(year, today.year, today.month));
+}
+
+export async function wizardPickMonth(
+  ctx: Context,
+  year: number,
+  month: number,
+): Promise<void> {
+  await ctx.answerCallbackQuery();
+  const op = await findOperator(ctx);
+  const tz = op?.defaultTimezone ?? DEFAULT_TIMEZONE;
+  const { todayYMD } = await import("../reminders/time-parsing.js");
+  const { reminderPickDayOfMonthMenu } = await import("./menus.js");
+  const today = todayYMD(tz);
+  await showMenu(
+    ctx,
+    reminderPickDayOfMonthMenu(year, month, today.year, today.month, today.day),
+  );
+}
+
+export async function wizardPickDayOfMonth(
+  ctx: Context,
+  year: number,
+  month: number,
+  day: number,
+): Promise<void> {
+  const op = await findOperator(ctx);
+  const tz = op?.defaultTimezone ?? DEFAULT_TIMEZONE;
+  const { dayOffsetFromYMD, formatCustomDay } = await import("../reminders/time-parsing.js");
+  const result = dayOffsetFromYMD(year, month, day, tz);
+  if (!result.ok) {
+    await ctx.answerCallbackQuery({ text: result.reason, show_alert: true });
+    return;
+  }
+  await ctx.answerCallbackQuery();
+  const { reminderPickHourMenu } = await import("./menus.js");
+  await showMenu(
+    ctx,
+    reminderPickHourMenu(formatCustomDay(result.dayOffset, tz), result.dayOffset),
+  );
+}
+
+export async function wizardNoop(ctx: Context): Promise<void> {
+  // Past months/days in the calendar use this to absorb taps without alerting.
   await ctx.answerCallbackQuery();
-  const userId = ctx.from?.id;
-  if (!userId) return;
-  updateWizard(userId, { step: "custom_date_input" });
-  const { reminderTypeDateMenu } = await import("./menus.js");
-  await showMenu(ctx, reminderTypeDateMenu());
 }
 
 export async function wizardPickHour(
diff --git a/apps/bot/src/telegram/menus.ts b/apps/bot/src/telegram/menus.ts
index bdba97e..59e3b22 100644
--- a/apps/bot/src/telegram/menus.ts
+++ b/apps/bot/src/telegram/menus.ts
@@ -402,7 +402,7 @@ export function reminderPickDayMenu(timezone: string): MenuView {
     }
     keyboard.row();
   }
-  keyboard.text("📝 Specific date…", "rmd:type").row();
+  keyboard.text("📅 Pick exact date…", "rmd:exact").row();
   keyboard.text("⬅ Back", "rm_t:back");
   // Plain text — IANA timezone names contain `_` which Markdown reads as italic.
   return {
@@ -412,12 +412,84 @@ export function reminderPickDayMenu(timezone: string): MenuView {
   };
 }
 
-export function reminderTypeDateMenu(): MenuView {
-  const keyboard = new InlineKeyboard().text("⬅ Back", "rm_t:custom");
+export function reminderPickYearMenu(currentYear: number): MenuView {
+  const keyboard = new InlineKeyboard();
+  // Show current year + next 4 years, two columns
+  const years = [currentYear, currentYear + 1, currentYear + 2, currentYear + 3, currentYear + 4];
+  for (let i = 0; i < years.length; i += 2) {
+    keyboard.text(String(years[i]!), `rmy:${years[i]}`);
+    if (years[i + 1] !== undefined) {
+      keyboard.text(String(years[i + 1]!), `rmy:${years[i + 1]}`);
+    }
+    keyboard.row();
+  }
+  keyboard.text("⬅ Back", "rm_t:custom");
   return {
-    text:
-      "📆 Type a date\n\nReply with a date in YYYY-MM-DD format, e.g. 2026-12-25.\n\n" +
-      "I'll then ask for the hour and minute.",
+    text: "📅 Exact date — Step A / D\n\nPick a year:",
+    keyboard,
+    parseMode: undefined,
+  };
+}
+
+const MONTH_NAMES = [
+  "Jan", "Feb", "Mar", "Apr", "May", "Jun",
+  "Jul", "Aug", "Sep", "Oct", "Nov", "Dec",
+];
+
+export function reminderPickMonthMenu(year: number, currentYear: number, currentMonth: number): MenuView {
+  const keyboard = new InlineKeyboard();
+  // Disable months in the past (only relevant when year === currentYear).
+  // 4 columns × 3 rows.
+  for (let row = 0; row < 3; row++) {
+    for (let col = 0; col < 4; col++) {
+      const month = row * 4 + col + 1; // 1..12
+      const isPast = year === currentYear && month < currentMonth;
+      const label = isPast ? `· ${MONTH_NAMES[month - 1]} ·` : MONTH_NAMES[month - 1]!;
+      // Past months use a no-op callback so taps just refresh the menu.
+      keyboard.text(label, isPast ? "rm_noop" : `rmM:${year}:${month}`);
+    }
+    keyboard.row();
+  }
+  keyboard.text("⬅ Back", "rmd:exact");
+  return {
+    text: `📅 Exact date — Step B / D\n\nYear: ${year}\n\nPick a month:`,
+    keyboard,
+    parseMode: undefined,
+  };
+}
+
+/**
+ * Calendar grid for the chosen year+month. Disables days strictly before today.
+ * `currentYear`, `currentMonth`, `currentDay` describe today in the operator's
+ * timezone. Returns a 7-column grid with Mon/Tue/.../Sun headers omitted (each
+ * cell is just the day number — keeps the keyboard compact).
+ */
+export function reminderPickDayOfMonthMenu(
+  year: number,
+  month: number,
+  currentYear: number,
+  currentMonth: number,
+  currentDay: number,
+): MenuView {
+  const daysInMonth = new Date(year, month, 0).getDate(); // month is 1-indexed; new Date(y, m, 0) gives last day of m-1
+  const keyboard = new InlineKeyboard();
+  let col = 0;
+  for (let day = 1; day <= daysInMonth; day++) {
+    const isPast =
+      (year === currentYear && month === currentMonth && day < currentDay) ||
+      (year === currentYear && month < currentMonth);
+    const label = isPast ? "·" : String(day).padStart(2, "0");
+    keyboard.text(label, isPast ? "rm_noop" : `rmD:${year}:${month}:${day}`);
+    col++;
+    if (col === 7) {
+      keyboard.row();
+      col = 0;
+    }
+  }
+  if (col > 0) keyboard.row();
+  keyboard.text("⬅ Back", `rmy:${year}`);
+  return {
+    text: `📅 Exact date — Step C / D\n\nYear: ${year}, Month: ${MONTH_NAMES[month - 1]}\n\nPick a day:`,
     keyboard,
     parseMode: undefined,
   };