diff --git a/api/src/routes/payday.ts b/api/src/routes/payday.ts
index c9a39e9..681909a 100644
--- a/api/src/routes/payday.ts
+++ b/api/src/routes/payday.ts
@@ -4,6 +4,8 @@ import { z } from "zod";
 import { fromZonedTime } from "date-fns-tz";
 import { getUserMidnight } from "../allocator.js";
 
+const DAY_MS = 24 * 60 * 60 * 1000;
+
 type RateLimitRouteOptions = {
   config: {
     rateLimit: {
@@ -100,15 +102,42 @@ const paydayRoutes: FastifyPluginAsync<PaydayRoutesOptions> = async (app, opts)
       userTimezone
     );
     const isPayday = isWithinPaydayWindow(now, nextPayday, 0, userTimezone);
-    const dayStart = getUserMidnight(userTimezone, now);
-    const dayEnd = new Date(dayStart.getTime() + 24 * 60 * 60 * 1000 - 1);
-    const scheduledIncomeToday = await app.prisma.incomeEvent.findFirst({
+
+    // Determine the currently due pay cycle:
+    // - on payday: cycle starts today
+    // - after payday: cycle starts on the last expected payday
+    const lookbackDaysByFrequency = {
+      weekly: 14,
+      biweekly: 28,
+      monthly: 62,
+    } as const;
+    const lookbackAnchor = new Date(
+      now.getTime() - lookbackDaysByFrequency[user.incomeFrequency] * DAY_MS
+    );
+    const currentCycleStart = calculateNextPayday(
+      user.firstIncomeDate,
+      user.incomeFrequency,
+      lookbackAnchor,
+      userTimezone
+    );
+    const isCycleDue = now.getTime() >= currentCycleStart.getTime();
+    const currentCycleEnd =
+      currentCycleStart.getTime() === nextPayday.getTime()
+        ? calculateNextPayday(
+            user.firstIncomeDate,
+            user.incomeFrequency,
+            new Date(nextPayday.getTime() + DAY_MS),
+            userTimezone
+          )
+        : nextPayday;
+
+    const scheduledIncomeInCurrentCycle = await app.prisma.incomeEvent.findFirst({
       where: {
         userId,
         isScheduledIncome: true,
         postedAt: {
-          gte: dayStart,
-          lte: dayEnd,
+          gte: currentCycleStart,
+          lt: currentCycleEnd,
         },
       },
       select: { id: true },
@@ -120,14 +149,17 @@ const paydayRoutes: FastifyPluginAsync<PaydayRoutesOptions> = async (app, opts)
       firstIncomeDate: user.firstIncomeDate.toISOString(),
       nextPayday: nextPayday.toISOString(),
       isPayday,
+      currentCycleStart: currentCycleStart.toISOString(),
+      currentCycleEnd: currentCycleEnd.toISOString(),
+      isCycleDue,
       pendingScheduledIncome: user.pendingScheduledIncome,
-      scheduledIncomeToday: !!scheduledIncomeToday,
-      shouldShowOverlay: isPayday && !scheduledIncomeToday,
+      scheduledIncomeInCurrentCycle: !!scheduledIncomeInCurrentCycle,
+      shouldShowOverlay: isCycleDue && !scheduledIncomeInCurrentCycle,
     });
 
     return {
-      shouldShowOverlay: isPayday && !scheduledIncomeToday,
-      pendingScheduledIncome: !scheduledIncomeToday,
+      shouldShowOverlay: isCycleDue && !scheduledIncomeInCurrentCycle,
+      pendingScheduledIncome: !scheduledIncomeInCurrentCycle,
       nextPayday: nextPayday.toISOString(),
     };
   });