diff --git a/apps/web/src/components/recurrence-picker.tsx b/apps/web/src/components/recurrence-picker.tsx
index b9e6a3f..7fce4b6 100644
--- a/apps/web/src/components/recurrence-picker.tsx
+++ b/apps/web/src/components/recurrence-picker.tsx
@@ -36,6 +36,9 @@ interface Draft {
   type: RuleType;
   /** Cron weekday list (0=Sun..6=Sat). */
   weekdays: number[];
+  /** Sorted unique day-of-month list (1-31) for monthly. */
+  monthDays: number[];
+  /** Single day-of-month (1-31) for yearly. */
   monthDay: number;
   month: number;
   /** Hour-of-day (0-23) for this rule's fire time. */
@@ -50,6 +53,7 @@ function defaultDraft(firstFire: DateTime): Draft {
   return {
     type: "daily",
     weekdays: [isoWeekdayToCron(firstFire.weekday)],
+    monthDays: [firstFire.day],
     monthDay: firstFire.day,
     month: firstFire.month,
     hour: firstFire.hour,
@@ -57,6 +61,10 @@ function defaultDraft(firstFire: DateTime): Draft {
   };
 }
 
+function uniqSortedDays(days: number[]): number[] {
+  return Array.from(new Set(days.filter((d) => d >= 1 && d <= 31))).sort((a, b) => a - b);
+}
+
 function pad2(n: number): string {
   return n.toString().padStart(2, "0");
 }
@@ -89,8 +97,11 @@ function draftToCron(d: Draft): string | null {
     case "weekly":
       if (!d.weekdays.length) return null;
       return `${m} ${h} * * ${d.weekdays.slice().sort((a, b) => a - b).join(",")}`;
-    case "monthly":
-      return `${m} ${h} ${clamp(d.monthDay, 1, 31)} * *`;
+    case "monthly": {
+      const days = uniqSortedDays(d.monthDays);
+      if (!days.length) return null;
+      return `${m} ${h} ${days.join(",")} * *`;
+    }
     case "yearly":
       return `${m} ${h} ${clamp(d.monthDay, 1, 31)} ${clamp(d.month, 1, 12)} *`;
   }
@@ -114,8 +125,15 @@ function describeDraft(d: Draft): string {
         .join(", ");
       return `Every week on ${labels} at ${t}`;
     }
-    case "monthly":
-      return `Every month on day ${clamp(d.monthDay, 1, 31)} at ${t}`;
+    case "monthly": {
+      const days = uniqSortedDays(d.monthDays);
+      if (!days.length) return "Pick at least one day";
+      const list =
+        days.length <= 6
+          ? days.join(", ")
+          : `${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 ${t}`;
   }
@@ -153,8 +171,15 @@ function draftFromCronExpr(expr: string, firstFire: DateTime): Draft {
       .filter((n) => n >= 0 && n <= 6);
     return { ...base, type: "weekly", weekdays: days, hour, minute };
   }
-  if ((m = rest.match(/^(\d+) \* \*$/))) {
-    return { ...base, type: "monthly", monthDay: Number(m[1]), hour, minute };
+  if ((m = rest.match(/^([0-9,]+) \* \*$/))) {
+    const days = uniqSortedDays(m[1]!.split(",").map((s) => Number(s)));
+    return {
+      ...base,
+      type: "monthly",
+      monthDays: days.length ? days : [1],
+      hour,
+      minute,
+    };
   }
   if ((m = rest.match(/^(\d+) (\d+) \*$/))) {
     return {
@@ -266,7 +291,7 @@ export function RecurrencePicker({ firstFire, value, onChange }: RecurrencePicke
 
       {drafts.length === 0 ? (
         <div className="rounded-xl border border-border bg-muted/20 px-3 py-3 text-sm text-muted-foreground">
-          Doesn&apos;t repeat — fires once at the date and time above.
+          No Repeats
         </div>
       ) : (
         <div className="overflow-hidden rounded-xl border border-border bg-card">
@@ -395,20 +420,42 @@ function RuleEditor({ draft, onChange }: RuleEditorProps) {
 
       <TabsContent value="monthly" className="space-y-3 pt-3">
         <div className="space-y-2">
-          <Label className="text-sm">Day of the month</Label>
-          <div className="flex items-center gap-2">
-            <Input
-              type="number"
-              min={1}
-              max={31}
-              value={draft.monthDay}
-              onChange={(e) => onChange({ monthDay: Number(e.target.value) || 1 })}
-              className="h-8 w-24"
-            />
+          <div className="flex items-center justify-between gap-2">
+            <Label className="text-sm">Days of the month</Label>
             <span className="text-xs text-muted-foreground">
-              Months without this day skip naturally (e.g. 31st)
+              {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">
+            Months without a selected day skip naturally (e.g. day 31 in February).
+          </p>
         </div>
         <TimeField draft={draft} onChange={onChange} />
       </TabsContent>