diff --git a/src/lib/medications/scheduling/__tests__/next-due.test.ts b/src/lib/medications/scheduling/__tests__/next-due.test.ts
new file mode 100644
index 000000000..c80bcadd2
--- /dev/null
+++ b/src/lib/medications/scheduling/__tests__/next-due.test.ts
@@ -0,0 +1,120 @@
+/**
+ * v1.8.5 — `computeNextDueAt` tests, focused on the rolling-cadence
+ * first-dose semantics.
+ *
+ * The server computes `nextDueAt` by asking the canonical engine for the
+ * earliest next slot across a medication's schedules. The medically
+ * important case: a rolling course whose `startsOn` is earlier today with
+ * no intake logged must surface its start dose as DUE/OVERDUE ("take
+ * now"), not roll it forward by N days (which also suppressed its
+ * reminder, since the worker shares the engine).
+ */
+import { describe, expect, it } from "vitest";
+
+import { computeNextDueAt } from "../next-due";
+import type {
+  WorkerMedicationRow,
+  WorkerScheduleRow,
+} from "../worker-helpers";
+
+function d(iso: string): Date {
+  return new Date(iso);
+}
+
+function makeMedication(
+  overrides: Partial<WorkerMedicationRow> = {},
+): WorkerMedicationRow {
+  return {
+    id: "med-1",
+    startsOn: null,
+    endsOn: null,
+    oneShot: false,
+    createdAt: d("2026-01-01T00:00:00Z"),
+    ...overrides,
+  };
+}
+
+function makeRollingSchedule(
+  overrides: Partial<WorkerScheduleRow> = {},
+): WorkerScheduleRow {
+  return {
+    id: "sched-1",
+    windowStart: "08:00",
+    windowEnd: "09:00",
+    daysOfWeek: null,
+    timesOfDay: ["08:00"],
+    reminderGraceMinutes: null,
+    rrule: null,
+    rollingIntervalDays: 7,
+    scheduleType: "SCHEDULED",
+    cyclicOnWeeks: null,
+    cyclicOffWeeks: null,
+    ...overrides,
+  };
+}
+
+const BERLIN = "Europe/Berlin";
+
+function berlinDay(date: Date): string {
+  return new Intl.DateTimeFormat("en-CA", {
+    timeZone: BERLIN,
+    year: "numeric",
+    month: "2-digit",
+    day: "2-digit",
+  }).format(date);
+}
+
+describe("computeNextDueAt — rolling first dose", () => {
+  it("surfaces an overdue first dose (past startsOn, no intake) as DUE today", () => {
+    const startsOn = d("2026-06-10T06:00:00Z"); // 08:00 Berlin slot is past
+    const now = d("2026-06-10T12:00:00Z"); // noon, after the slot
+    const next = computeNextDueAt({
+      medication: makeMedication({ startsOn }),
+      schedules: [makeRollingSchedule()],
+      now,
+      userTz: BERLIN,
+      lastIntakeAt: null,
+    });
+    expect(next).not.toBeNull();
+    expect(next!.getTime()).toBeLessThan(now.getTime()); // overdue
+    expect(berlinDay(next!)).toBe("2026-06-10");
+  });
+
+  it("returns the future first dose AT startsOn (no intake) without adding N", () => {
+    const startsOn = d("2026-06-12T00:00:00Z");
+    const now = d("2026-06-10T12:00:00Z");
+    const next = computeNextDueAt({
+      medication: makeMedication({ startsOn }),
+      schedules: [makeRollingSchedule()],
+      now,
+      userTz: BERLIN,
+      lastIntakeAt: null,
+    });
+    expect(next).not.toBeNull();
+    expect(berlinDay(next!)).toBe("2026-06-12");
+  });
+
+  it("re-anchors on lastIntakeAt + N once an intake exists", () => {
+    const now = d("2026-06-10T12:00:00Z");
+    const next = computeNextDueAt({
+      medication: makeMedication({ startsOn: d("2026-06-01T00:00:00Z") }),
+      schedules: [makeRollingSchedule()],
+      now,
+      userTz: BERLIN,
+      lastIntakeAt: d("2026-06-09T08:00:00Z"),
+    });
+    expect(next).not.toBeNull();
+    expect(berlinDay(next!)).toBe("2026-06-16"); // 2026-06-09 + 7d
+  });
+
+  it("returns null when no schedules", () => {
+    const next = computeNextDueAt({
+      medication: makeMedication(),
+      schedules: [],
+      now: d("2026-06-10T12:00:00Z"),
+      userTz: BERLIN,
+      lastIntakeAt: null,
+    });
+    expect(next).toBeNull();
+  });
+});
diff --git a/src/lib/medications/scheduling/__tests__/recurrence.test.ts b/src/lib/medications/scheduling/__tests__/recurrence.test.ts
index 9dbfcb921..daaa9fa2b 100644
--- a/src/lib/medications/scheduling/__tests__/recurrence.test.ts
+++ b/src/lib/medications/scheduling/__tests__/recurrence.test.ts
@@ -279,9 +279,12 @@ describe("occurrencesBetween — rolling", () => {
     );
   });
 
-  it("rollingIntervalDays=7 + lastIntakeAt=null + startsOn=T-2d emits one at T+5d", () => {
+  it("rollingIntervalDays=7 + lastIntakeAt=null + future startsOn → first dose due AT startsOn (not startsOn+N)", () => {
+    // v1.8.5 — with no intake yet the FIRST rolling dose lands ON the
+    // start date, not start + N. A future startsOn therefore emits its
+    // slot at startsOn itself.
     const NOW = d("2026-06-10T12:00:00Z");
-    const startsOn = new Date(NOW.getTime() - 2 * 24 * 60 * 60 * 1000);
+    const startsOn = new Date(NOW.getTime() + 2 * 24 * 60 * 60 * 1000);
     const schedule = makeSchedule({
       rollingIntervalDays: 7,
       timesOfDay: ["08:00"],
@@ -294,7 +297,7 @@ describe("occurrencesBetween — rolling", () => {
     const to = new Date(NOW.getTime() + 14 * 24 * 60 * 60 * 1000);
     const slots = occurrencesBetween(schedule, from, to, ctx);
     expect(slots).toHaveLength(1);
-    const expectedDay = new Date(startsOn.getTime() + 7 * 24 * 60 * 60 * 1000);
+    // The slot is the start dose itself (startsOn), NOT startsOn + 7d.
     expect(
       new Intl.DateTimeFormat("en-CA", {
         timeZone: "Europe/Berlin",
@@ -308,10 +311,36 @@ describe("occurrencesBetween — rolling", () => {
         year: "numeric",
         month: "2-digit",
         day: "2-digit",
-      }).format(expectedDay),
+      }).format(startsOn),
     );
   });
 
+  it("rollingIntervalDays=7 + lastIntakeAt=null + startsOn=today → first dose due today", () => {
+    // Fresh rolling course starting today: the start dose is due today,
+    // not seven days out.
+    const startsOn = d("2026-06-10T00:00:00Z");
+    const schedule = makeSchedule({
+      rollingIntervalDays: 7,
+      timesOfDay: ["08:00"],
+    });
+    const ctx = makeCtx({
+      lastIntakeAt: null,
+      medication: { startsOn },
+    });
+    const from = d("2026-06-10T00:00:00Z");
+    const to = d("2026-06-24T23:59:59Z");
+    const slots = occurrencesBetween(schedule, from, to, ctx);
+    expect(slots).toHaveLength(1);
+    expect(
+      new Intl.DateTimeFormat("en-CA", {
+        timeZone: "Europe/Berlin",
+        year: "numeric",
+        month: "2-digit",
+        day: "2-digit",
+      }).format(slots[0].at),
+    ).toBe("2026-06-10");
+  });
+
   it("rolling terminates when endsOn falls before next-due", () => {
     const NOW = d("2026-06-10T12:00:00Z");
     const lastIntake = new Date(NOW.getTime() - 3 * 24 * 60 * 60 * 1000);
@@ -332,6 +361,84 @@ describe("occurrencesBetween — rolling", () => {
     );
     expect(slots).toHaveLength(0);
   });
+
+  it("nextOccurrenceAfter surfaces an overdue first dose (past startsOn, no intake) as DUE today", () => {
+    // v1.8.5 — a rolling course whose startsOn is earlier today with no
+    // intake logged yet must surface the start dose as DUE/OVERDUE, not
+    // roll it forward by N. The strict `> now` filter previously dropped
+    // it; the rolling branch now floors to the start of the user's day.
+    const startsOn = d("2026-06-10T06:00:00Z"); // 08:00 Berlin slot is past
+    const NOW = d("2026-06-10T12:00:00Z"); // noon — after the 08:00 slot
+    const schedule = makeSchedule({
+      rollingIntervalDays: 7,
+      timesOfDay: ["08:00"],
+    });
+    const ctx = makeCtx({
+      lastIntakeAt: null,
+      medication: { startsOn },
+    });
+    const next = nextOccurrenceAfter(schedule, NOW, ctx);
+    expect(next).not.toBeNull();
+    // The surfaced slot is today's start dose (08:00 Berlin), already in
+    // the past relative to NOW — i.e. overdue, "take now".
+    expect(next!.at.getTime()).toBeLessThan(NOW.getTime());
+    expect(
+      new Intl.DateTimeFormat("en-CA", {
+        timeZone: "Europe/Berlin",
+        year: "numeric",
+        month: "2-digit",
+        day: "2-digit",
+      }).format(next!.at),
+    ).toBe("2026-06-10");
+  });
+
+  it("nextOccurrenceAfter returns the future first dose AT startsOn (no intake) without adding N", () => {
+    const NOW = d("2026-06-10T12:00:00Z");
+    const startsOn = d("2026-06-12T00:00:00Z"); // 2 days out
+    const schedule = makeSchedule({
+      rollingIntervalDays: 7,
+      timesOfDay: ["08:00"],
+    });
+    const ctx = makeCtx({
+      lastIntakeAt: null,
+      medication: { startsOn },
+    });
+    const next = nextOccurrenceAfter(schedule, NOW, ctx);
+    expect(next).not.toBeNull();
+    expect(
+      new Intl.DateTimeFormat("en-CA", {
+        timeZone: "Europe/Berlin",
+        year: "numeric",
+        month: "2-digit",
+        day: "2-digit",
+      }).format(next!.at),
+    ).toBe("2026-06-12");
+  });
+
+  it("nextOccurrenceAfter re-anchors on lastIntakeAt + N after an intake", () => {
+    // The v1.8.4 re-anchor must stay: once an intake exists, the next
+    // slot is lastIntakeAt + N, NOT the start date.
+    const NOW = d("2026-06-10T12:00:00Z");
+    const lastIntake = d("2026-06-09T08:00:00Z");
+    const schedule = makeSchedule({
+      rollingIntervalDays: 7,
+      timesOfDay: ["08:00"],
+    });
+    const ctx = makeCtx({
+      lastIntakeAt: lastIntake,
+      medication: { startsOn: d("2026-06-01T00:00:00Z") },
+    });
+    const next = nextOccurrenceAfter(schedule, NOW, ctx);
+    expect(next).not.toBeNull();
+    expect(
+      new Intl.DateTimeFormat("en-CA", {
+        timeZone: "Europe/Berlin",
+        year: "numeric",
+        month: "2-digit",
+        day: "2-digit",
+      }).format(next!.at),
+    ).toBe("2026-06-16"); // 2026-06-09 + 7d
+  });
 });
 
 // ────────────────────────────────────────────────────────────────────
diff --git a/src/lib/medications/scheduling/recurrence.ts b/src/lib/medications/scheduling/recurrence.ts
index 6496ad39c..8b59e1bd5 100644
--- a/src/lib/medications/scheduling/recurrence.ts
+++ b/src/lib/medications/scheduling/recurrence.ts
@@ -16,10 +16,11 @@
  *   1. **One-shot** (`medication.oneShot === true`) — single slot at
  *      the anchor date, one per `timesOfDay` entry.
  *   2. **Rolling** (`schedule.rollingIntervalDays !== null`) — next
- *      slot is `lastIntakeAt + N days` (or `startsOn + N days` if
- *      the user has never logged an intake). Only the immediately
- *      next slot is emitted; further slots depend on the user
- *      actually logging the intake.
+ *      slot is `lastIntakeAt + N days`. With no intake yet the FIRST
+ *      dose is due AT `startsOn ?? createdAt` (not `+ N`); the `+ N`
+ *      cadence only begins once the first intake is logged. Only the
+ *      immediately next slot is emitted; further slots depend on the
+ *      user actually logging the intake.
  *   3. **RRULE** (`schedule.rrule !== null`) — RFC 5545 expansion
  *      via the `rrule` npm lib. Day-anchored dates are returned in
  *      UTC by the library; each `timesOfDay` entry is then applied
@@ -248,15 +249,19 @@ export function nextOccurrenceAfter(
   }
 
   // Rolling is also single-slot (only emits the immediately next).
+  //
+  // v1.8.5 — floor the search window to the start of the user's current
+  // day rather than the strict `after` instant. A rolling dose whose slot
+  // lands earlier today (a past `startsOn` with no intake, or an overdue
+  // `lastIntakeAt + N`) is DUE/OVERDUE and must surface as "take now",
+  // not be skipped by a strict `> now` filter. Flooring to start-of-day
+  // keeps a slot the user has not yet acted on visible through the rest
+  // of its due day instead of silently rolling it forward by N.
   if (schedule.rollingIntervalDays !== null) {
-    const slots = expandRolling(
-      schedule,
-      ctx,
-      new Date(after.getTime() + 1),
-      limit,
-    );
+    const dayFloor = startOfDayInTz(after, ctx.timeZone);
+    const slots = expandRolling(schedule, ctx, dayFloor, limit);
     for (const s of slots) {
-      if (s.at.getTime() <= after.getTime()) continue;
+      if (s.at.getTime() < dayFloor.getTime()) continue;
       if (cyclic && !isInCyclicOnWeek(s.at, schedule, ctx)) continue;
       return s;
     }
@@ -334,9 +339,21 @@ function expandOneShot(
 // ────────────────────────────────────────────────────────────────────
 
 /**
- * Rolling cadence — "every N days from last intake". Emits one
- * occurrence at `(lastIntakeAt ?? startsOn ?? createdAt) + N days`,
- * applied at the first `timesOfDay` entry (or `windowStart`).
+ * Rolling cadence — "every N days from last intake".
+ *
+ * Anchoring (v1.8.5 — medically-correct first dose):
+ *   - After an intake → next slot is `lastIntakeAt + N days` (the
+ *     v1.8.4 re-anchor). Logging a dose pushes the next one out by N.
+ *   - No intake yet → the FIRST dose is due AT `startsOn ?? createdAt`,
+ *     NOT `start + N`. A rolling course's first dose lands on the start
+ *     date; the `+ N` cadence only kicks in once the first intake is
+ *     logged. The pre-v1.8.5 engine emitted `start + N` here, which
+ *     silently skipped the start-date dose (and suppressed its reminder,
+ *     since the worker shares this engine).
+ *
+ * A past `startsOn` with no intake therefore surfaces the start dose as
+ * DUE/OVERDUE ("take now") via `nextOccurrenceAfter`'s rolling branch,
+ * rather than rolling it forward.
  *
  * Design choice: only the FIRST time-of-day entry is emitted even
  * when multiple are configured. The rolling semantic — "every N days
@@ -358,10 +375,13 @@ function expandRolling(
 ): Occurrence[] {
   const n = schedule.rollingIntervalDays;
   if (n === null || n <= 0) return [];
-  const anchor =
-    ctx.lastIntakeAt ?? ctx.medication.startsOn ?? ctx.medication.createdAt;
 
-  const nextDue = new Date(anchor.getTime() + n * DAY_MS);
+  // After an intake the next dose is N days out. With no intake yet the
+  // FIRST dose is the start date itself (no `+ N`) — see the doc comment.
+  const nextDue =
+    ctx.lastIntakeAt !== null
+      ? new Date(ctx.lastIntakeAt.getTime() + n * DAY_MS)
+      : ctx.medication.startsOn ?? ctx.medication.createdAt;
 
   // endsOn cap.
   if (
@@ -560,6 +580,16 @@ function applyTimeOfDayToDate(day: Date, hhmm: string, tz: string): Date {
   return guess;
 }
 
+/**
+ * The UTC instant of midnight (00:00 wall-clock) on `instant`'s day in
+ * the user's IANA timezone. Used by the rolling-cadence next-due search
+ * to floor the window to the start of the user's current day so an
+ * overdue / due-earlier-today rolling dose still surfaces.
+ */
+function startOfDayInTz(instant: Date, tz: string): Date {
+  return applyTimeOfDayToDate(instant, "00:00", tz);
+}
+
 function tzOffsetMinutes(date: Date, tz: string): number {
   const parts = wallClockInTz(date, tz);
   const asIfUtc = Date.UTC(