diff --git a/apps/web/src/components/recurrence-picker.tsx b/apps/web/src/components/recurrence-picker.tsx
index 7fce4b6..c95fa98 100644
--- a/apps/web/src/components/recurrence-picker.tsx
+++ b/apps/web/src/components/recurrence-picker.tsx
@@ -36,11 +36,10 @@ interface Draft {
   type: RuleType;
   /** Cron weekday list (0=Sun..6=Sat). */
   weekdays: number[];
-  /** Sorted unique day-of-month list (1-31) for monthly. */
+  /** Sorted unique day-of-month list (1-31). Used by monthly + yearly. */
   monthDays: number[];
-  /** Single day-of-month (1-31) for yearly. */
-  monthDay: number;
-  month: number;
+  /** Sorted unique month list (1-12). Used by yearly only. */
+  months: number[];
   /** Hour-of-day (0-23) for this rule's fire time. */
   hour: number;
   /** Minute-of-hour (0-59). */
@@ -54,8 +53,7 @@ function defaultDraft(firstFire: DateTime): Draft {
     type: "daily",
     weekdays: [isoWeekdayToCron(firstFire.weekday)],
     monthDays: [firstFire.day],
-    monthDay: firstFire.day,
-    month: firstFire.month,
+    months: [firstFire.month],
     hour: firstFire.hour,
     minute: firstFire.minute,
   };
@@ -65,6 +63,10 @@ function uniqSortedDays(days: number[]): number[] {
   return Array.from(new Set(days.filter((d) => d >= 1 && d <= 31))).sort((a, b) => a - b);
 }
 
+function uniqSortedMonths(months: number[]): number[] {
+  return Array.from(new Set(months.filter((m) => m >= 1 && m <= 12))).sort((a, b) => a - b);
+}
+
 function pad2(n: number): string {
   return n.toString().padStart(2, "0");
 }
@@ -102,8 +104,12 @@ function draftToCron(d: Draft): string | null {
       if (!days.length) return null;
       return `${m} ${h} ${days.join(",")} * *`;
     }
-    case "yearly":
-      return `${m} ${h} ${clamp(d.monthDay, 1, 31)} ${clamp(d.month, 1, 12)} *`;
+    case "yearly": {
+      const days = uniqSortedDays(d.monthDays);
+      const months = uniqSortedMonths(d.months);
+      if (!days.length || !months.length) return null;
+      return `${m} ${h} ${days.join(",")} ${months.join(",")} *`;
+    }
   }
 }
 
@@ -134,8 +140,18 @@ function describeDraft(d: Draft): string {
           : `${days.slice(0, 6).join(", ")} +${days.length - 6} more`;
       return `Every month on day${days.length > 1 ? "s" : ""} ${list} at ${t}`;
     }
-    case "yearly":
-      return `Every year on ${MONTH_NAMES[clamp(d.month, 1, 12) - 1]} ${clamp(d.monthDay, 1, 31)} at ${t}`;
+    case "yearly": {
+      const days = uniqSortedDays(d.monthDays);
+      const months = uniqSortedMonths(d.months);
+      if (!days.length) return "Pick at least one day";
+      if (!months.length) return "Pick at least one month";
+      const monthLabel = months.map((mo) => MONTH_NAMES[mo - 1]?.slice(0, 3)).join(", ");
+      const dayLabel =
+        days.length <= 6
+          ? days.join(", ")
+          : `${days.slice(0, 6).join(", ")} +${days.length - 6} more`;
+      return `Every year in ${monthLabel} on day${days.length > 1 ? "s" : ""} ${dayLabel} at ${t}`;
+    }
   }
 }
 
@@ -181,12 +197,14 @@ function draftFromCronExpr(expr: string, firstFire: DateTime): Draft {
       minute,
     };
   }
-  if ((m = rest.match(/^(\d+) (\d+) \*$/))) {
+  if ((m = rest.match(/^([0-9,]+) ([0-9,]+) \*$/))) {
+    const days = uniqSortedDays(m[1]!.split(",").map((s) => Number(s)));
+    const months = uniqSortedMonths(m[2]!.split(",").map((s) => Number(s)));
     return {
       ...base,
       type: "yearly",
-      monthDay: Number(m[1]),
-      month: Number(m[2]),
+      monthDays: days.length ? days : [1],
+      months: months.length ? months : [1],
       hour,
       minute,
     };
@@ -461,33 +479,82 @@ function RuleEditor({ draft, onChange }: RuleEditorProps) {
       </TabsContent>
 
       <TabsContent value="yearly" className="space-y-3 pt-3">
-        <div className="flex flex-wrap items-end gap-3">
-          <div className="space-y-1">
-            <Label className="text-xs text-muted-foreground">Month</Label>
-            <select
-              value={draft.month}
-              onChange={(e) => onChange({ month: Number(e.target.value) })}
-              className="h-8 rounded-lg border border-input bg-background px-2 text-sm focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-ring"
-            >
-              {MONTH_NAMES.map((name, i) => (
-                <option key={name} value={i + 1}>
-                  {name}
-                </option>
-              ))}
-            </select>
+        <div className="space-y-2">
+          <div className="flex items-center justify-between gap-2">
+            <Label className="text-sm">Months</Label>
+            <span className="text-xs text-muted-foreground">
+              {draft.months.length} selected
+            </span>
           </div>
-          <div className="space-y-1">
-            <Label className="text-xs text-muted-foreground">Day</Label>
-            <Input
-              type="number"
-              min={1}
-              max={31}
-              value={draft.monthDay}
-              onChange={(e) => onChange({ monthDay: Number(e.target.value) || 1 })}
-              className="h-8 w-20"
-            />
+          <div className="grid grid-cols-6 gap-1">
+            {MONTH_NAMES.map((name, i) => {
+              const month = i + 1;
+              const active = draft.months.includes(month);
+              return (
+                <button
+                  key={month}
+                  type="button"
+                  onClick={() =>
+                    onChange({
+                      months: active
+                        ? draft.months.filter((mo) => mo !== month)
+                        : uniqSortedMonths([...draft.months, month]),
+                    })
+                  }
+                  aria-pressed={active}
+                  className={cn(
+                    "inline-flex h-8 items-center justify-center rounded-md border text-xs font-medium transition-colors",
+                    active
+                      ? "border-primary bg-primary text-primary-foreground"
+                      : "border-border bg-background hover:border-primary/50 hover:bg-primary/5 hover:text-primary",
+                  )}
+                >
+                  {name.slice(0, 3)}
+                </button>
+              );
+            })}
           </div>
         </div>
+
+        <div className="space-y-2">
+          <div className="flex items-center justify-between gap-2">
+            <Label className="text-sm">Days</Label>
+            <span className="text-xs text-muted-foreground">
+              {draft.monthDays.length} selected
+            </span>
+          </div>
+          <div className="grid grid-cols-7 gap-1">
+            {Array.from({ length: 31 }, (_, i) => i + 1).map((day) => {
+              const active = draft.monthDays.includes(day);
+              return (
+                <button
+                  key={day}
+                  type="button"
+                  onClick={() =>
+                    onChange({
+                      monthDays: active
+                        ? draft.monthDays.filter((d) => d !== day)
+                        : uniqSortedDays([...draft.monthDays, day]),
+                    })
+                  }
+                  aria-pressed={active}
+                  className={cn(
+                    "inline-flex h-8 items-center justify-center rounded-md border text-xs font-medium transition-colors",
+                    active
+                      ? "border-primary bg-primary text-primary-foreground"
+                      : "border-border bg-background hover:border-primary/50 hover:bg-primary/5 hover:text-primary",
+                  )}
+                >
+                  {day}
+                </button>
+              );
+            })}
+          </div>
+          <p className="text-xs text-muted-foreground">
+            Fires on every selected day of every selected month.
+          </p>
+        </div>
+
         <TimeField draft={draft} onChange={onChange} />
       </TabsContent>
     </Tabs>