diff --git a/src/reminders/worker.test.ts b/src/reminders/worker.test.ts
index 5df7cb1..d72e2e2 100644
--- a/src/reminders/worker.test.ts
+++ b/src/reminders/worker.test.ts
@@ -1,4 +1,4 @@
-import { expect, test } from "bun:test";
+import { expect, test, spyOn } from "bun:test";
 import { eq } from "drizzle-orm";
 import { fixture } from "../habits/test-fixture";
 import { reminderDeliveries, reminderSettings } from "../db/schema";
@@ -213,3 +213,21 @@ test("messages include names only for the applicable reminders in the delivery b
     expect(JSON.parse(sent[1]!).allowed_mentions.parse).toEqual([]);
   } finally { f.close(); }
 });
+
+
+test('delivered slots skip habit evaluation while later slots and retries remain eligible', async () => {
+  const { f } = await setup(); const sent: string[] = [];
+  const { HabitService } = await import('../habits/service');
+  let sync: ReturnType<typeof spyOn> | undefined;
+  try {
+    f.db.update(reminderSettings).set({ quietStart: '00:00', quietEnd: '00:00', reminders: [
+      { type: 'date', date: '2026-09-04', time: '10:00' }, { type: 'date', date: '2026-09-04', time: '12:00' },
+    ] }).run();
+    const tick = (clock: string) => sendDueReminders(f.db, config, transport(sent), () => Date.parse(`2026-09-04T${clock}:00Z`));
+    await tick('08:00'); expect(sent).toHaveLength(1);
+    sync = spyOn(HabitService.prototype, 'sync');
+    for (let i = 0; i < 5; i++) await tick('08:30');
+    expect(sync).not.toHaveBeenCalled(); expect(sent).toHaveLength(1);
+    await tick('10:00'); expect(sync).toHaveBeenCalled(); expect(sent).toHaveLength(2);
+  } finally { sync?.mockRestore(); f.close(); }
+});
diff --git a/src/reminders/worker.ts b/src/reminders/worker.ts
index b987ec3..86ac3d3 100644
--- a/src/reminders/worker.ts
+++ b/src/reminders/worker.ts
@@ -22,14 +22,26 @@ export async function sendDueReminders(db: AppDatabase, config: ReminderConfig,
   // Retain recent delivery history and deduplication records without unbounded growth.
   db.delete(reminderDeliveries).where(lt(reminderDeliveries.updatedAt, now() - 90 * 86400000)).run();
   for (const { user } of rows) {
-    function due() {
+    function due(checkDeliveries = false) {
       const currentUser = db.select().from(users).where(eq(users.id, user.id)).get();
       const prefs = db.select().from(reminderSettings).where(eq(reminderSettings.userId, user.id)).get();
       if (!currentUser || !prefs?.enabled) return null;
       const timestamp = now(); const clock = localClock(timestamp, currentUser.timezone);
       if (inQuietHours(clock, prefs.quietStart, prefs.quietEnd)) return null;
-      const times = timesForDate(prefs, localDate(timestamp, currentUser.timezone)).filter(time => time <= clock);
+      const date = localDate(timestamp, currentUser.timezone);
+      const times = timesForDate(prefs, date).filter(time => time <= clock);
       if (!times.length) return null;
+      if (checkDeliveries) {
+        const previous = db.select().from(reminderDeliveries).where(and(eq(reminderDeliveries.userId, user.id), eq(reminderDeliveries.date, date))).all();
+        // This is only a cheap eligibility hint. The transaction below still owns claims.
+        // Let stale pending records reach its recovery step before skipping the user.
+        const stalePending = previous.some(row => row.status === 'pending' && row.updatedAt < timestamp - 60000);
+        if (!stalePending) {
+          const legacy = previous.find(row => row.slot === '*');
+          const claimable = (prior: typeof previous[number] | undefined) => !prior || (prior.status === 'deferred' && (prior.retryAt ?? 0) <= timestamp);
+          if (previous.some(row => row.status === 'pending') || (legacy ? !claimable(legacy) : !times.some(slot => claimable(previous.find(row => row.slot === slot))))) return null;
+        }
+      }
       const service = new HabitService(db, { id: currentUser.id, discordId: currentUser.discordId, username: currentUser.username, displayName: currentUser.globalName ?? currentUser.username, avatarUrl: null, timezone: currentUser.timezone }, timestamp);
       service.sync();
       // Avoid sending an artificial "today" after a backwards timezone change.
@@ -37,7 +49,7 @@ export async function sendDueReminders(db: AppDatabase, config: ReminderConfig,
       const remaining = service.list().filter(habit => { const day = service.day(habit.id, service.today); return day.due && !day.complete; }).length;
       return remaining ? { date: service.today, remaining, timezone: currentUser.timezone, times, entries: entriesForDate(prefs, service.today) } : null;
     }
-    const initial = due(); if (!initial) continue;
+    const initial = due(true); if (!initial) continue;
     const claims = db.transaction(tx => {
       // A crashed/aborted send must not block later times indefinitely.
       tx.update(reminderDeliveries).set({ status: "uncertain" }).where(and(eq(reminderDeliveries.userId, user.id), eq(reminderDeliveries.status, "pending"), lt(reminderDeliveries.updatedAt, now() - 60000))).run();