diff --git a/client/src/components/Planner/DayPlanSidebar.tsx b/client/src/components/Planner/DayPlanSidebar.tsx
index 91ad626d..0072eb7d 100644
--- a/client/src/components/Planner/DayPlanSidebar.tsx
+++ b/client/src/components/Planner/DayPlanSidebar.tsx
@@ -18,7 +18,7 @@ import { useTripStore } from '../../store/tripStore'
 import { useCanDo } from '../../store/permissionsStore'
 import { useSettingsStore } from '../../store/settingsStore'
 import { useTranslation } from '../../i18n'
-import { isDayInAccommodationRange, getAccommodationAnchors } from '../../utils/dayOrder'
+import { isDayInAccommodationRange, getAccommodationAnchors, getDayBookendHotels } from '../../utils/dayOrder'
 import {
   TRANSPORT_TYPES, parseTimeToMinutes, getSpanPhase, getDisplayTimeForDay, getTransportRouteEndpoints,
   getTransportForDay as _getTransportForDay, getMergedItems as _getMergedItems,
@@ -407,30 +407,29 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
     }
     if (cur.length >= 2) runs.push(cur)
 
-    // Hotel bookend legs: the drive from the day's accommodation to the first
-    // located place (morning) and from the last place back to it (evening). Only
-    // when the "optimize from accommodation" setting is on and the day has a hotel,
-    // mirroring the range logic the optimizer itself uses (getAccommodationAnchors).
+    // Hotel bookend legs: the drive from the day's accommodation to the first located
+    // waypoint of the day (morning) and from the last one back to it (evening). Only when
+    // the "optimize from accommodation" setting is on and the day has a hotel.
     const day = days.find(d => d.id === selectedDayId)
-    const dayAccs = day && optimizeFromAccommodation !== false
-      ? accommodations.filter(a => a.place_lat != null && a.place_lng != null && isDayInAccommodationRange(day, a.start_day_id, a.end_day_id, days))
-      : []
-    const checkOut = day ? dayAccs.find(a => a.end_day_id === day.id) : undefined
-    const checkIn = day ? dayAccs.find(a => a.start_day_id === day.id) : undefined
-    const transfer = !!(checkOut && checkIn && checkOut !== checkIn)
-    const startHotel = transfer ? checkOut : dayAccs[0]
-    const endHotel = transfer ? checkIn : dayAccs[0]
+    const { morning: startHotel, evening: endHotel } =
+      day && optimizeFromAccommodation !== false ? getDayBookendHotels(day, days, accommodations) : {}
     const hotelName = (a: Accommodation) => (a as any).place_name || (a as any).reservation_title || ''
-    const placePts: { lat: number; lng: number }[] = []
+    // Waypoints include transport endpoints (a car return, a taxi/train arrival), so the hotel
+    // legs connect even when the day starts or ends with a booking rather than a place.
+    const wayPts: { lat: number; lng: number }[] = []
     for (const it of merged) {
       if (it.type === 'place' && it.data.place?.lat && it.data.place?.lng) {
-        placePts.push({ lat: it.data.place.lat, lng: it.data.place.lng })
+        wayPts.push({ lat: it.data.place.lat, lng: it.data.place.lng })
+      } else if (it.type === 'transport') {
+        const { from, to } = getTransportRouteEndpoints(it.data, selectedDayId)
+        if (from) wayPts.push({ lat: from.lat, lng: from.lng })
+        if (to) wayPts.push({ lat: to.lat, lng: to.lng })
       }
     }
-    const firstPlace = placePts[0]
-    const lastPlace = placePts[placePts.length - 1]
-    const wantTop = !!(startHotel && firstPlace)
-    const wantBottom = !!(endHotel && lastPlace)
+    const firstWay = wayPts[0]
+    const lastWay = wayPts[wayPts.length - 1]
+    const wantTop = !!(startHotel && firstWay)
+    const wantBottom = !!(endHotel && lastWay)
 
     if (runs.length === 0 && !wantTop && !wantBottom) { setRouteLegs({}); setHotelLegs({}); return }
 
@@ -456,11 +455,11 @@ function useDayPlanSidebar(props: DayPlanSidebarProps) {
       }
       const hotel: { top?: { seg: RouteSegment; name: string }; bottom?: { seg: RouteSegment; name: string } } = {}
       if (wantTop) {
-        const seg = await legBetween({ lat: startHotel!.place_lat as number, lng: startHotel!.place_lng as number }, { lat: firstPlace.lat, lng: firstPlace.lng })
+        const seg = await legBetween({ lat: startHotel!.place_lat as number, lng: startHotel!.place_lng as number }, { lat: firstWay.lat, lng: firstWay.lng })
         if (seg) hotel.top = { seg, name: hotelName(startHotel!) }
       }
       if (wantBottom) {
-        const seg = await legBetween({ lat: lastPlace.lat, lng: lastPlace.lng }, { lat: endHotel!.place_lat as number, lng: endHotel!.place_lng as number })
+        const seg = await legBetween({ lat: lastWay.lat, lng: lastWay.lng }, { lat: endHotel!.place_lat as number, lng: endHotel!.place_lng as number })
         if (seg) hotel.bottom = { seg, name: hotelName(endHotel!) }
       }
 
diff --git a/client/src/utils/dayOrder.test.ts b/client/src/utils/dayOrder.test.ts
index 8640d6b4..4aac45a8 100644
--- a/client/src/utils/dayOrder.test.ts
+++ b/client/src/utils/dayOrder.test.ts
@@ -1,6 +1,6 @@
 import { describe, it, expect } from 'vitest'
 import type { Day, Accommodation } from '../types'
-import { getDayOrder, isDayInAccommodationRange, getAccommodationAnchors } from './dayOrder'
+import { getDayOrder, isDayInAccommodationRange, getAccommodationAnchors, getDayBookendHotels } from './dayOrder'
 
 const days = [
   { id: 10, day_number: 1 },
@@ -70,4 +70,51 @@ describe('getAccommodationAnchors', () => {
     const accs = [hotel({ start_day_id: 10, end_day_id: 30, place_lat: null, place_lng: null })]
     expect(getAccommodationAnchors(days[1], days, accs)).toEqual({})
   })
+
+  it('keeps morning/evening correct on a transfer day when the morning stay runs long (#887)', () => {
+    const accs = [
+      hotel({ start_day_id: 10, end_day_id: 30, place_lat: 1, place_lng: 1 }), // slept here, checks out later
+      hotel({ start_day_id: 20, end_day_id: 30, place_lat: 9, place_lng: 9 }), // check-in today
+    ]
+    expect(getAccommodationAnchors(days[1], days, accs)).toEqual({
+      start: { lat: 1, lng: 1 },
+      end: { lat: 9, lng: 9 },
+    })
+  })
+})
+
+describe('getDayBookendHotels', () => {
+  it('returns nothing when the day has no accommodation', () => {
+    expect(getDayBookendHotels(days[1], days, [])).toEqual({})
+  })
+
+  it('bookends both ends with the single hotel on a normal stay day', () => {
+    const h = hotel({ start_day_id: 10, end_day_id: 30 })
+    const { morning, evening } = getDayBookendHotels(days[1], days, [h])
+    expect(morning).toBe(h)
+    expect(evening).toBe(h)
+  })
+
+  it('uses the checked-out hotel in the morning and the checked-in hotel in the evening on a transfer day', () => {
+    const out = hotel({ start_day_id: 10, end_day_id: 20, place_lat: 1, place_lng: 1 })
+    const into = hotel({ start_day_id: 20, end_day_id: 30, place_lat: 9, place_lng: 9 })
+    const { morning, evening } = getDayBookendHotels(days[1], days, [out, into])
+    expect(morning).toBe(out)
+    expect(evening).toBe(into)
+  })
+
+  it('still picks the slept-in hotel for the morning when its stay does not end on the transfer day (#887)', () => {
+    // The morning hotel runs long (checks out day 3) so it is not flagged as "checks out today";
+    // the old "ends today" rule collapsed both bookends onto the arriving hotel.
+    const stayed = hotel({ start_day_id: 10, end_day_id: 30, place_lat: 1, place_lng: 1 })
+    const into = hotel({ start_day_id: 20, end_day_id: 30, place_lat: 9, place_lng: 9 })
+    const { morning, evening } = getDayBookendHotels(days[1], days, [stayed, into])
+    expect(morning).toBe(stayed)
+    expect(evening).toBe(into)
+  })
+
+  it('ignores accommodations without coordinates', () => {
+    const h = hotel({ place_lat: null, place_lng: null })
+    expect(getDayBookendHotels(days[1], days, [h])).toEqual({})
+  })
 })
diff --git a/client/src/utils/dayOrder.ts b/client/src/utils/dayOrder.ts
index c96b948b..1332a7b0 100644
--- a/client/src/utils/dayOrder.ts
+++ b/client/src/utils/dayOrder.ts
@@ -3,6 +3,36 @@ import type { Day, Accommodation, RouteAnchors } from '../types'
 export const getDayOrder = (day: Day, days: Day[]): number =>
   day.day_number ?? days.indexOf(day)
 
+// The two hotels that bookend a day: the one you woke up in (morning) and the one you sleep in
+// tonight (evening). On a transfer day these differ; on any other day both are the single hotel.
+// The morning hotel is keyed off "checked in on an earlier day and still in range" (i.e. you slept
+// there) rather than "checks out today", so it stays correct when an overlapping or long stay does
+// not end exactly on the transfer day.
+export const getDayBookendHotels = (
+  day: Day,
+  days: Day[],
+  accommodations: Accommodation[],
+): { morning?: Accommodation; evening?: Accommodation } => {
+  const inRange = accommodations.filter(a =>
+    a.place_lat != null && a.place_lng != null &&
+    isDayInAccommodationRange(day, a.start_day_id, a.end_day_id, days),
+  )
+  if (inRange.length === 0) return {}
+
+  const dayOrd = getDayOrder(day, days)
+  const orderOf = (id: number) => {
+    const d = days.find(x => x.id === id)
+    return d ? getDayOrder(d, days) : dayOrd
+  }
+  const checkIn = inRange.find(a => a.start_day_id === day.id) // the hotel you arrive at tonight
+  const sleptHere = inRange.find(a => orderOf(a.start_day_id) < dayOrd) // the hotel you woke up in
+
+  return {
+    morning: sleptHere ?? checkIn ?? inRange[0],
+    evening: checkIn ?? sleptHere ?? inRange[0],
+  }
+}
+
 // Derives route anchors from the accommodation(s) active on a day. A single hotel is the day's home
 // base, so the route is a loop that starts and ends there. A transfer day — checking out of one hotel
 // and into another — instead runs from the morning hotel to the evening one.
@@ -11,22 +41,12 @@ export const getAccommodationAnchors = (
   days: Day[],
   accommodations: Accommodation[],
 ): RouteAnchors => {
-  const located = accommodations.filter(a =>
-    a.place_lat != null && a.place_lng != null &&
-    isDayInAccommodationRange(day, a.start_day_id, a.end_day_id, days),
-  )
-  if (located.length === 0) return {}
-
-  const toAnchor = (a: Accommodation) => ({ lat: a.place_lat as number, lng: a.place_lng as number })
-
-  const checkOut = located.find(a => a.end_day_id === day.id) // the hotel you leave this morning
-  const checkIn = located.find(a => a.start_day_id === day.id) // the hotel you arrive at tonight
-  if (checkOut && checkIn && checkOut !== checkIn) {
-    return { start: toAnchor(checkOut), end: toAnchor(checkIn) }
+  const { morning, evening } = getDayBookendHotels(day, days, accommodations)
+  if (!morning || !evening) return {}
+  return {
+    start: { lat: morning.place_lat as number, lng: morning.place_lng as number },
+    end: { lat: evening.place_lat as number, lng: evening.place_lng as number },
   }
-
-  const hotel = toAnchor(located[0])
-  return { start: hotel, end: hotel }
 }
 
 export const isDayInAccommodationRange = (