diff --git a/src/lib/fitbit/__tests__/client.test.ts b/src/lib/fitbit/__tests__/client.test.ts
index 23bbf4081..483bf42d5 100644
--- a/src/lib/fitbit/__tests__/client.test.ts
+++ b/src/lib/fitbit/__tests__/client.test.ts
@@ -503,6 +503,62 @@ describe("sleep mapping (1.2 levels.data)", () => {
     expect(mapSleepSession({ levels: { data: [] } })).toHaveLength(0);
     expect(mapSleepSession({})).toHaveLength(0);
   });
+
+  it("anchors a near-midnight segment END to the user's timezone, not the process zone", () => {
+    // A Berlin user (UTC+2 in May / CEST) whose last segment ENDS at 00:30
+    // local on 2026-05-11. The offset-less wall clock `2026-05-11T00:30:00`
+    // must resolve to 22:30 UTC on 2026-05-10 — NOT 00:30 UTC (which a bare
+    // `new Date(iso)` in a UTC process would produce, flipping the wake-day).
+    const sessions = readSleepSessions({
+      sleep: [
+        {
+          logId: 4242,
+          startTime: "2026-05-10T23:00:00.000",
+          endTime: "2026-05-11T00:30:00.000",
+          levels: {
+            data: [
+              {
+                dateTime: "2026-05-11T00:00:00.000",
+                level: "deep",
+                seconds: 1800, // ends 00:30 Berlin local
+              },
+            ],
+          },
+        },
+      ],
+    });
+
+    const out = mapSleepSession(sessions[0]!, "Europe/Berlin");
+    expect(out).toHaveLength(1);
+    // 00:30 CEST (UTC+2) → 22:30 UTC on the PRIOR civil day.
+    expect(out[0]!.measuredAt.toISOString()).toBe("2026-05-10T22:30:00.000Z");
+  });
+
+  it("anchors a logId-less session anchor against the user's timezone", () => {
+    const sessions = readSleepSessions({
+      sleep: [
+        {
+          // No logId → the anchor falls back to the END instant, which must
+          // also be tz-resolved so the externalId is stable across syncs.
+          endTime: "2026-05-11T00:30:00.000",
+          levels: {
+            data: [
+              {
+                dateTime: "2026-05-11T00:00:00.000",
+                level: "rem",
+                seconds: 1800,
+              },
+            ],
+          },
+        },
+      ],
+    });
+
+    const out = mapSleepSession(sessions[0]!, "Europe/Berlin");
+    expect(out).toHaveLength(1);
+    // anchor = end instant ISO (UTC) → fieldTag starts with that instant.
+    expect(out[0]!.fieldTag).toBe("2026-05-10T22:30:00.000Z:sleep_rem:0");
+  });
 });
 
 describe("workout mapping (activities list)", () => {
diff --git a/src/lib/fitbit/client.ts b/src/lib/fitbit/client.ts
index 22a59049f..e5eab0e07 100644
--- a/src/lib/fitbit/client.ts
+++ b/src/lib/fitbit/client.ts
@@ -39,6 +39,7 @@
 import { createHash, randomBytes } from "node:crypto";
 import { getEvent } from "@/lib/logging/context";
 import { safeFetch } from "@/lib/safe-fetch";
+import { zonedWallClockToUtc } from "@/lib/tz/wall-clock";
 import { FitbitApiError, classifyFitbitResponse } from "./response-classifier";
 
 /** Classic Fitbit Web API base. */
@@ -929,13 +930,13 @@ interface FitbitSleepSession {
  * The stable session anchor for a sleep externalId — the logId, else the end (or
  * start) instant. A re-scored night reuses the same logId → overwrites in place.
  */
-function sleepSessionAnchor(s: FitbitSleepSession): string {
+function sleepSessionAnchor(s: FitbitSleepSession, tz?: string): string {
   if (typeof s.logId === "number" && Number.isFinite(s.logId)) {
     return String(s.logId);
   }
   for (const t of [s.endTime, s.startTime]) {
     if (typeof t === "string") {
-      const d = parseLocalInstant(t);
+      const d = parseLocalInstant(t, tz);
       if (d) return d.toISOString();
     }
   }
@@ -943,12 +944,40 @@ function sleepSessionAnchor(s: FitbitSleepSession): string {
 }
 
 /**
- * Parse a Fitbit sleep timestamp. The 1.2 sleep log emits LOCAL wall-clock ISO
- * strings WITHOUT an offset (e.g. `2020-01-26T03:02:30.000`); `new Date(...)`
- * treats an offset-less ISO string as local time, which is the user's intent
- * here (the night belongs to the user's local clock). Returns null on a miss.
+ * Matches an offset-less local ISO wall-clock string Fitbit emits on the classic
+ * sleep + activity logs (`2020-01-26T03:02:30` / `...T03:02:30.000`). No trailing
+ * `Z`, no `±hh:mm` — those denote an absolute instant and are honoured verbatim.
  */
-function parseLocalInstant(iso: string): Date | null {
+const OFFSET_LESS_LOCAL_ISO =
+  /^(\d{4})-(\d{2})-(\d{2})[T ](\d{2}):(\d{2})(?::(\d{2}))?(?:\.\d+)?$/;
+
+/**
+ * Parse a Fitbit timestamp into a UTC instant. The classic 1.2 sleep log and the
+ * activities list emit LOCAL wall-clock strings WITHOUT an offset (e.g.
+ * `2020-01-26T03:02:30.000`) — the night/activity belongs to the user's local
+ * clock, so the wall clock must be resolved against the USER'S timezone, not the
+ * process zone. A bare `new Date(iso)` parses an offset-less string in the host
+ * zone (UTC in production), which shifts a non-UTC user's segment by their UTC
+ * offset and can flip the wake-day in the night reconstruction. When `tz` is
+ * omitted (no user zone on the path) the host-local fallback preserves the prior
+ * behaviour. Strings that DO carry an offset/`Z` are absolute and parsed as-is.
+ * Returns null on a miss.
+ */
+function parseLocalInstant(iso: string, tz?: string): Date | null {
+  const m = OFFSET_LESS_LOCAL_ISO.exec(iso.trim());
+  if (m) {
+    return zonedWallClockToUtc(
+      {
+        year: Number(m[1]),
+        month: Number(m[2]),
+        day: Number(m[3]),
+        hour: Number(m[4]),
+        minute: Number(m[5]),
+        second: m[6] ? Number(m[6]) : 0,
+      },
+      tz,
+    );
+  }
   const d = new Date(iso);
   return Number.isNaN(d.getTime()) ? null : d;
 }
@@ -959,14 +988,20 @@ function parseLocalInstant(iso: string): Date | null {
  * Each segment carries a stage-scoped, INDEXED fieldTag so the several segments
  * of one stage stay distinct under the `(userId, type, source, externalId)`
  * dedup key. Unknown stage labels are skipped.
+ *
+ * The 1.2 sleep log emits OFFSET-LESS local wall-clock timestamps, so `tz` (the
+ * user's stored zone) anchors them to the correct UTC instant — without it a
+ * non-UTC user's near-midnight segment END would shift by their UTC offset and
+ * could land on the wrong wake-day in the night reconstruction.
  */
 export function mapSleepSession(
   session: FitbitSleepSession,
+  tz?: string,
 ): FitbitMappedMeasurement[] {
   const data = session.levels?.data;
   if (!Array.isArray(data) || data.length === 0) return [];
 
-  const anchor = sleepSessionAnchor(session);
+  const anchor = sleepSessionAnchor(session, tz);
   const out: FitbitMappedMeasurement[] = [];
   let segIndex = 0;
   for (const seg of data) {
@@ -975,7 +1010,7 @@ export function mapSleepSession(
     if (!positive(seg.seconds)) continue;
     const startStr = typeof seg.dateTime === "string" ? seg.dateTime : null;
     if (!startStr) continue;
-    const start = parseLocalInstant(startStr);
+    const start = parseLocalInstant(startStr, tz);
     if (!start) continue;
     const minutes = seg.seconds / 60;
     const end = new Date(start.getTime() + seg.seconds * 1000);
@@ -1083,13 +1118,18 @@ export interface FitbitMappedWorkout {
  * there is no usable start + positive duration. The externalId anchors on the
  * `logId` (stable) so a re-fetch overwrites the same row. The classic
  * activities-list endpoint does not surface min/max HR, so those stay null.
+ *
+ * `startTime` is an offset-less local wall-clock string, so `tz` (the user's
+ * stored zone) anchors it to the correct UTC instant rather than the process
+ * zone.
  */
 export function mapWorkout(
   entry: FitbitActivityLogEntry,
+  tz?: string,
 ): FitbitMappedWorkout | null {
   const start =
     typeof entry.startTime === "string"
-      ? parseLocalInstant(entry.startTime)
+      ? parseLocalInstant(entry.startTime, tz)
       : null;
   if (!start) return null;
   if (!positive(entry.duration)) return null;
diff --git a/src/lib/fitbit/sync-sleep.ts b/src/lib/fitbit/sync-sleep.ts
index 2215d4ef8..662cfbc46 100644
--- a/src/lib/fitbit/sync-sleep.ts
+++ b/src/lib/fitbit/sync-sleep.ts
@@ -32,6 +32,7 @@ import {
   type FitbitResourceSyncOptions,
 } from "./sync";
 import { annotate } from "@/lib/logging/context";
+import { resolveUserTimezone } from "@/lib/tz/resolver";
 
 export async function syncUserSleep(
   userId: string,
@@ -40,6 +41,11 @@ export async function syncUserSleep(
   const tokenInfo = await getValidToken(userId);
   if (!tokenInfo) return 0;
 
+  // The classic 1.2 sleep log emits offset-less local wall-clock timestamps;
+  // anchor them against the user's stored zone so a near-midnight segment END
+  // lands on the correct wake-day rather than being shifted by the process zone.
+  const tz = await resolveUserTimezone(userId);
+
   const start = opts.start ?? new Date(Date.now() - 30 * 24 * 60 * 60 * 1000);
   const end = opts.end ?? new Date();
   const windows = chunkDateRanges(start, end, FITBIT_SLEEP_RANGE_DAYS);
@@ -53,7 +59,7 @@ export async function syncUserSleep(
       return handleCollectionFetchError("fetchSleep", userId, err);
     }
     for (const session of readSleepSessions(body)) {
-      for (const m of mapSleepSession(session)) {
+      for (const m of mapSleepSession(session, tz)) {
         readings.push({
           type: m.type,
           value: m.value,
diff --git a/src/lib/fitbit/sync-workout.ts b/src/lib/fitbit/sync-workout.ts
index 7e38a3872..a430e85f7 100644
--- a/src/lib/fitbit/sync-workout.ts
+++ b/src/lib/fitbit/sync-workout.ts
@@ -29,6 +29,7 @@ import {
 } from "./sync";
 import { prisma } from "@/lib/db";
 import { annotate, getEvent } from "@/lib/logging/context";
+import { resolveUserTimezone } from "@/lib/tz/resolver";
 
 /** Activities per page on the `activities/list` walk. */
 const WORKOUT_PAGE_SIZE = 100;
@@ -42,6 +43,10 @@ export async function syncUserWorkout(
   const tokenInfo = await getValidToken(userId);
   if (!tokenInfo) return 0;
 
+  // `startTime` on the activities list is offset-less local wall-clock; anchor
+  // it to the user's stored zone rather than the process zone.
+  const tz = await resolveUserTimezone(userId);
+
   const afterDate =
     opts.start ?? new Date(Date.now() - 30 * 24 * 60 * 60 * 1000);
 
@@ -67,7 +72,7 @@ export async function syncUserWorkout(
 
   let imported = 0;
   for (const entry of entries) {
-    const w: FitbitMappedWorkout | null = mapWorkout(entry);
+    const w: FitbitMappedWorkout | null = mapWorkout(entry, tz);
     if (!w) continue; // no usable time span — not a workout
 
     try {
diff --git a/src/lib/tz/__tests__/local-day.test.ts b/src/lib/tz/__tests__/local-day.test.ts
index f116dd3bb..e9eac4f8c 100644
--- a/src/lib/tz/__tests__/local-day.test.ts
+++ b/src/lib/tz/__tests__/local-day.test.ts
@@ -1,6 +1,46 @@
 import { describe, expect, it } from "vitest";
 import { startOfLocalDayInTz } from "@/lib/tz/local-day";
-import { wallClockInTz } from "@/lib/tz/wall-clock";
+import { wallClockInTz, zonedWallClockToUtc } from "@/lib/tz/wall-clock";
+
+describe("zonedWallClockToUtc", () => {
+  it("resolves a wall clock in a positive-offset zone to the right UTC instant", () => {
+    // 00:30 CEST (UTC+2) on 2026-05-11 → 22:30 UTC on 2026-05-10.
+    const utc = zonedWallClockToUtc(
+      { year: 2026, month: 5, day: 11, hour: 0, minute: 30 },
+      "Europe/Berlin",
+    );
+    expect(utc.toISOString()).toBe("2026-05-10T22:30:00.000Z");
+  });
+
+  it("round-trips through wallClockInTz across the spring-forward boundary", () => {
+    // 03:30 local on Berlin's spring-forward day (clocks jumped 02:00→03:00).
+    const utc = zonedWallClockToUtc(
+      { year: 2026, month: 3, day: 29, hour: 3, minute: 30 },
+      "Europe/Berlin",
+    );
+    const parts = wallClockInTz(utc, "Europe/Berlin");
+    expect(parts.hour).toBe(3);
+    expect(parts.minute).toBe(30);
+    expect(parts.day).toBe(29);
+  });
+
+  it("resolves a negative-offset zone", () => {
+    // 00:30 NZST (UTC+12) on 2026-06-15 → 12:30 UTC on 2026-06-14.
+    const utc = zonedWallClockToUtc(
+      { year: 2026, month: 6, day: 15, hour: 0, minute: 30 },
+      "Pacific/Auckland",
+    );
+    expect(utc.toISOString()).toBe("2026-06-14T12:30:00.000Z");
+  });
+
+  it("falls back to host-local when tz is undefined", () => {
+    const utc = zonedWallClockToUtc(
+      { year: 2026, month: 6, day: 15, hour: 14, minute: 30, second: 15 },
+      undefined,
+    );
+    expect(utc.getTime()).toBe(new Date(2026, 5, 15, 14, 30, 15).getTime());
+  });
+});
 
 describe("startOfLocalDayInTz", () => {
   it("anchors at the user's local midnight, not UTC midnight", () => {
diff --git a/src/lib/tz/wall-clock.ts b/src/lib/tz/wall-clock.ts
index 4dc5efcf5..68df50b26 100644
--- a/src/lib/tz/wall-clock.ts
+++ b/src/lib/tz/wall-clock.ts
@@ -64,6 +64,75 @@ const WALL_CLOCK_OPTIONS: Omit<Intl.DateTimeFormatOptions, "timeZone"> =
     weekday: "short",
   });
 
+/**
+ * The wall-clock fields a `zonedWallClockToUtc` caller supplies. Months are
+ * 1-based to match `WallClockParts`; second defaults to 0 when omitted.
+ */
+export interface WallClockInput {
+  year: number;
+  /** 1–12 (January = 1, December = 12). */
+  month: number;
+  /** 1–31. */
+  day: number;
+  /** 0–23. */
+  hour: number;
+  minute: number;
+  second?: number;
+}
+
+/**
+ * Inverse of `wallClockInTz`: given the wall-clock an observer in `tz` reads
+ * (e.g. an offset-less `2020-01-26T03:02:30` Fitbit sleep timestamp), return the
+ * UTC instant it denotes. DST-safe via the same two-pass converge as
+ * `startOfLocalDayInTz` — the second pass settles the zone offset across a DST
+ * transition for every IANA zone. When `tz` is omitted the parts are read as the
+ * host's system-local clock so offset-less callers keep their legacy shape.
+ */
+export function zonedWallClockToUtc(
+  parts: WallClockInput,
+  tz: string | undefined,
+): Date {
+  const second = parts.second ?? 0;
+  if (!tz) {
+    return new Date(
+      parts.year,
+      parts.month - 1,
+      parts.day,
+      parts.hour,
+      parts.minute,
+      second,
+      0,
+    );
+  }
+  // Treat the wall clock as if it were UTC, then correct by the zone offset at
+  // that approximate instant; one extra pass settles the DST boundary.
+  const asIfUtc = Date.UTC(
+    parts.year,
+    parts.month - 1,
+    parts.day,
+    parts.hour,
+    parts.minute,
+    second,
+    0,
+  );
+  let guess = new Date(asIfUtc);
+  for (let i = 0; i < 2; i++) {
+    const at = wallClockInTz(guess, tz);
+    const guessAsIfUtc = Date.UTC(
+      at.year,
+      at.month - 1,
+      at.day,
+      at.hour,
+      at.minute,
+      at.second,
+      0,
+    );
+    const offsetMin = Math.round((guessAsIfUtc - guess.getTime()) / 60_000);
+    guess = new Date(asIfUtc - offsetMin * 60_000);
+  }
+  return guess;
+}
+
 export function wallClockInTz(
   date: Date,
   tz: string | undefined,