diff --git a/client/src/components/Journey/JourneyDetailPageDatePicker.tsx b/client/src/components/Journey/JourneyDetailPageDatePicker.tsx
index 8da27b91..4b35ef0b 100644
--- a/client/src/components/Journey/JourneyDetailPageDatePicker.tsx
+++ b/client/src/components/Journey/JourneyDetailPageDatePicker.tsx
@@ -15,7 +15,8 @@ export function DatePicker({ value, onChange, tripDates }: {
   })
 
   const daysInMonth = new Date(viewMonth.year, viewMonth.month + 1, 0).getDate()
-  const firstDow = new Date(viewMonth.year, viewMonth.month, 1).getDay()
+  // Monday-first, matching CustomDateTimePicker / VacayCalendar (getDay() is Sunday=0).
+  const firstDow = (new Date(viewMonth.year, viewMonth.month, 1).getDay() + 6) % 7
   const monthName = new Date(viewMonth.year, viewMonth.month).toLocaleDateString(undefined, { month: 'long', year: 'numeric' })
 
   const prevMonth = () => {
@@ -68,7 +69,7 @@ export function DatePicker({ value, onChange, tripDates }: {
 
             {/* Weekday headers */}
             <div className="grid grid-cols-7 mb-1">
-              {['Su', 'Mo', 'Tu', 'We', 'Th', 'Fr', 'Sa'].map((d, i) => (
+              {['Mo', 'Tu', 'We', 'Th', 'Fr', 'Sa', 'Su'].map((d, i) => (
                 <div key={i} className="text-center text-[10px] font-medium text-zinc-400 py-1">{d}</div>
               ))}
             </div>
diff --git a/client/src/components/Journey/JourneyDetailPageSettingsDialog.tsx b/client/src/components/Journey/JourneyDetailPageSettingsDialog.tsx
index 7c00f110..2273617c 100644
--- a/client/src/components/Journey/JourneyDetailPageSettingsDialog.tsx
+++ b/client/src/components/Journey/JourneyDetailPageSettingsDialog.tsx
@@ -10,6 +10,7 @@ import JourneyShareSection from './JourneyShareSection'
 import type { JourneyDetail } from '../../store/journeyStore'
 import { pickGradient } from '../../pages/journeyDetail/JourneyDetailPage.helpers'
 import { AddTripDialog } from './JourneyDetailPageAddTripDialog'
+import { normalizeImageFile } from '../../utils/convertHeic'
 
 export function JourneySettingsDialog({ journey, onClose, onSaved, onOpenInvite, onRefresh }: {
   journey: JourneyDetail
@@ -49,7 +50,7 @@ export function JourneySettingsDialog({ journey, onClose, onSaved, onOpenInvite,
     const file = e.target.files?.[0]
     if (!file) return
     const formData = new FormData()
-    formData.append('cover', file)
+    formData.append('cover', await normalizeImageFile(file))
     try {
       await journeyApi.uploadCover(journey.id, formData)
       toast.success(t('journey.settings.coverUpdated'))
diff --git a/client/src/components/Map/MapViewGL.tsx b/client/src/components/Map/MapViewGL.tsx
index 73f50f1c..e86f75ee 100644
--- a/client/src/components/Map/MapViewGL.tsx
+++ b/client/src/components/Map/MapViewGL.tsx
@@ -447,7 +447,7 @@ export function MapViewGL({
       geometry: { type: 'LineString' as const, coordinates: seg.map(([lat, lng]) => [lng, lat]) },
     }))
     src.setData({ type: 'FeatureCollection', features })
-  }, [route])
+  }, [route, mapReady])
 
   // Travel times now live in the day sidebar (per-segment connectors), not on the map.
 
@@ -470,7 +470,7 @@ export function MapViewGL({
       } catch { return [] }
     })
     src.setData({ type: 'FeatureCollection', features })
-  }, [places])
+  }, [places, mapReady])
 
   // Reservation overlay — mirrors the Leaflet ReservationOverlay: great-
   // circle arcs for flights/cruises, straight lines for trains/cars,
diff --git a/client/src/components/Planner/FileImportModal.tsx b/client/src/components/Planner/FileImportModal.tsx
index e5b452f9..2e752afa 100644
--- a/client/src/components/Planner/FileImportModal.tsx
+++ b/client/src/components/Planner/FileImportModal.tsx
@@ -31,7 +31,7 @@ export default function FileImportModal({ isOpen, onClose, tripId, pushUndo, ini
   const loadTrip = useTripStore((s) => s.loadTrip)
   const fileInputRef = useRef<HTMLInputElement>(null)
 
-  const [file, setFile] = useState<File | null>(null)
+  const [files, setFiles] = useState<File[]>([])
   const [isDragOver, setIsDragOver] = useState(false)
   const [loading, setLoading] = useState(false)
   const [error, setError] = useState('')
@@ -51,7 +51,7 @@ export default function FileImportModal({ isOpen, onClose, tripId, pushUndo, ini
   }
 
   const reset = () => {
-    setFile(null)
+    setFiles([])
     setIsDragOver(false)
     setLoading(false)
     setError('')
@@ -67,14 +67,14 @@ export default function FileImportModal({ isOpen, onClose, tripId, pushUndo, ini
     if (initialFile) {
       const err = validateFile(initialFile)
       if (err) {
-        setFile(null)
+        setFiles([])
         setError(err)
       } else {
-        setFile(initialFile)
+        setFiles([initialFile])
         setError('')
       }
     } else {
-      setFile(null)
+      setFiles([])
       setError('')
     }
   // validateFile uses t() which is stable — intentionally omitted from deps
@@ -86,22 +86,32 @@ export default function FileImportModal({ isOpen, onClose, tripId, pushUndo, ini
     onClose()
   }
 
-  const selectFile = (f: File) => {
-    const validationError = validateFile(f)
-    if (validationError) {
-      setError(validationError)
-      setFile(null)
+  const selectFiles = (incoming: File[]) => {
+    if (incoming.length === 0) return
+    const valid: File[] = []
+    let firstError: string | null = null
+    for (const f of incoming) {
+      const validationError = validateFile(f)
+      if (validationError) {
+        firstError = firstError ?? validationError
+        continue
+      }
+      valid.push(f)
+    }
+    if (valid.length === 0) {
+      setError(firstError ?? '')
+      setFiles([])
       return
     }
-    setFile(f)
-    setError('')
+    setFiles(valid)
+    setError(firstError ?? '')
     setSummary(null)
   }
 
   const handleInputChange = (e: React.ChangeEvent<HTMLInputElement>) => {
-    const f = e.target.files?.[0]
+    const list = e.target.files ? Array.from(e.target.files) : []
     e.target.value = ''
-    if (f) selectFile(f)
+    if (list.length) selectFiles(list)
   }
 
   const handleDragOver = (e: React.DragEvent) => {
@@ -116,71 +126,92 @@ export default function FileImportModal({ isOpen, onClose, tripId, pushUndo, ini
   const handleDrop = (e: React.DragEvent) => {
     e.preventDefault()
     setIsDragOver(false)
-    const f = e.dataTransfer.files[0]
-    if (f) selectFile(f)
+    const list = Array.from(e.dataTransfer.files)
+    if (list.length) selectFiles(list)
   }
 
   const handleImport = async () => {
-    if (!file || loading) return
-    const ext = file.name.toLowerCase().split('.').pop()
+    if (files.length === 0 || loading) return
     setLoading(true)
     setError('')
     setSummary(null)
 
-    try {
-      if (ext === 'gpx') {
-        const result = await placesApi.importGpx(tripId, file, gpxOpts)
-        await loadTrip(tripId)
-        if (result.count === 0 && result.skipped > 0) {
-          toast.warning(t('places.importAllSkipped'))
+    let totalCreated = 0
+    let totalSkipped = 0
+    const createdIds: number[] = []
+    const errors: string[] = []
+    let mergedSummary: PlacesImportSummary | null = null
+    let importedGpx = false
+    let importedKml = false
+
+    for (const f of files) {
+      const ext = f.name.toLowerCase().split('.').pop()
+      try {
+        if (ext === 'gpx') {
+          importedGpx = true
+          const result = await placesApi.importGpx(tripId, f, gpxOpts)
+          totalCreated += result.count ?? 0
+          totalSkipped += result.skipped ?? 0
+          if (result.places?.length > 0) createdIds.push(...result.places.map((p: { id: number }) => p.id))
         } else {
-          toast.success(t('places.gpxImported', { count: result.count }))
-        }
-        if (result.places?.length > 0) {
-          const importedIds: number[] = result.places.map((p: { id: number }) => p.id)
-          pushUndo?.(t('undo.importGpx'), async () => {
-            try { await placesApi.bulkDelete(tripId, importedIds) } catch {}
-            await loadTrip(tripId)
-          })
-        }
-        handleClose()
-      } else {
-        const result = await placesApi.importMapFile(tripId, file, kmlOpts)
-        await loadTrip(tripId)
-        setSummary(result.summary || null)
-        if (result.count === 0 && (result.summary?.skippedCount ?? 0) > 0) {
-          toast.warning(t('places.importAllSkipped'))
-        } else {
-          toast.success(t('places.kmlKmzImported', { count: result.count }))
-        }
-        if (result.summary?.errors?.length > 0) {
-          setError(result.summary.errors.join('\n'))
-        }
-        if (result.places?.length > 0) {
-          const importedIds: number[] = result.places.map((p: { id: number }) => p.id)
-          pushUndo?.(t('undo.importKeyholeMarkup'), async () => {
-            try { await placesApi.bulkDelete(tripId, importedIds) } catch {}
-            await loadTrip(tripId)
-          })
+          importedKml = true
+          const result = await placesApi.importMapFile(tripId, f, kmlOpts)
+          totalCreated += result.count ?? 0
+          if (result.places?.length > 0) createdIds.push(...result.places.map((p: { id: number }) => p.id))
+          const s = result.summary as PlacesImportSummary | undefined
+          if (s) {
+            mergedSummary = mergedSummary
+              ? {
+                  totalPlacemarks: mergedSummary.totalPlacemarks + s.totalPlacemarks,
+                  createdCount: mergedSummary.createdCount + s.createdCount,
+                  skippedCount: mergedSummary.skippedCount + s.skippedCount,
+                  warnings: [...mergedSummary.warnings, ...(s.warnings ?? [])],
+                  errors: [...mergedSummary.errors, ...(s.errors ?? [])],
+                }
+              : s
+            totalSkipped += s.skippedCount ?? 0
+          }
         }
+      } catch (err: any) {
+        const message = err?.response?.data?.error || t('places.importFileError')
+        errors.push(files.length > 1 ? `${f.name}: ${message}` : message)
       }
-    } catch (err: any) {
-      const responseSummary = err?.response?.data?.summary as PlacesImportSummary | undefined
-      if (responseSummary) setSummary(responseSummary)
-      const message = err?.response?.data?.error || t('places.importFileError')
-      setError(message)
-      toast.error(message)
-    } finally {
-      setLoading(false)
     }
+
+    await loadTrip(tripId)
+
+    if (createdIds.length > 0) {
+      pushUndo?.(importedGpx && !importedKml ? t('undo.importGpx') : t('undo.importKeyholeMarkup'), async () => {
+        try { await placesApi.bulkDelete(tripId, createdIds) } catch {}
+        await loadTrip(tripId)
+      })
+    }
+
+    if (totalCreated > 0) {
+      const key = importedKml && !importedGpx ? 'places.kmlKmzImported' : 'places.gpxImported'
+      toast.success(t(key, { count: totalCreated }))
+    } else if (totalSkipped > 0 && errors.length === 0) {
+      toast.warning(t('places.importAllSkipped'))
+    }
+
+    if (mergedSummary) setSummary(mergedSummary)
+    if (errors.length > 0) {
+      setError(errors.join('\n'))
+      toast.error(errors[0])
+    }
+
+    setLoading(false)
+
+    // Close once everything succeeded and there's no KML summary left to surface.
+    if (errors.length === 0 && !mergedSummary) handleClose()
   }
 
-  const fileExt = file?.name.toLowerCase().split('.').pop() ?? ''
-  const isGpx = fileExt === 'gpx'
-  const isKml = fileExt === 'kml' || fileExt === 'kmz'
+  const exts = files.map(f => f.name.toLowerCase().split('.').pop() ?? '')
+  const isGpx = exts.includes('gpx')
+  const isKml = exts.some(e => e === 'kml' || e === 'kmz')
   const gpxNoneSelected = isGpx && !gpxOpts.waypoints && !gpxOpts.routes && !gpxOpts.tracks
   const kmlNoneSelected = isKml && !kmlOpts.points && !kmlOpts.paths
-  const canImport = !!file && !loading && !gpxNoneSelected && !kmlNoneSelected
+  const canImport = files.length > 0 && !loading && !gpxNoneSelected && !kmlNoneSelected
 
   if (!isOpen) return null
 
@@ -206,6 +237,7 @@ export default function FileImportModal({ isOpen, onClose, tripId, pushUndo, ini
           ref={fileInputRef}
           type="file"
           accept=".gpx,.kml,.kmz"
+          multiple
           style={{ display: 'none' }}
           onChange={handleInputChange}
         />
@@ -240,8 +272,8 @@ export default function FileImportModal({ isOpen, onClose, tripId, pushUndo, ini
           <Upload size={18} strokeWidth={1.8} color={isDragOver ? 'var(--accent)' : 'var(--text-faint)'} style={{ pointerEvents: 'none' }} />
           {isDragOver ? (
             <span className="text-accent" style={{ pointerEvents: 'none' }}>{t('places.importFileDropActive')}</span>
-          ) : file ? (
-            <span style={{ color: 'var(--text-primary)', textAlign: 'center', wordBreak: 'break-all', pointerEvents: 'none' }}>{file.name}</span>
+          ) : files.length > 0 ? (
+            <span style={{ color: 'var(--text-primary)', textAlign: 'center', wordBreak: 'break-all', pointerEvents: 'none' }}>{files.map(f => f.name).join(', ')}</span>
           ) : (
             <span style={{ color: 'var(--text-faint)', textAlign: 'center', pointerEvents: 'none' }}>{t('places.importFileDropHere')}</span>
           )}
diff --git a/client/src/components/Planner/PlaceFormModal.test.tsx b/client/src/components/Planner/PlaceFormModal.test.tsx
index 4ddfae0e..2dea519d 100644
--- a/client/src/components/Planner/PlaceFormModal.test.tsx
+++ b/client/src/components/Planner/PlaceFormModal.test.tsx
@@ -225,13 +225,16 @@ describe('PlaceFormModal', () => {
     expect(screen.getByDisplayValue('48.8584')).toBeInTheDocument();
   });
 
-  it('FE-PLANNER-PLACEFORM-021: maps search error shows toast', async () => {
+  it('FE-PLANNER-PLACEFORM-021: maps search error surfaces the server-provided reason', async () => {
     const addToast = vi.fn();
     window.__addToast = addToast;
 
     const user = userEvent.setup();
+    // The backend forwards the real upstream error (e.g. a Google Places API message);
+    // the modal must show it instead of a generic "search failed" so the cause is visible.
     server.use(
-      http.post('/api/maps/search', () => HttpResponse.json({ error: 'fail' }, { status: 500 })),
+      http.post('/api/maps/search', () =>
+        HttpResponse.json({ error: 'Places API (New) has not been used in project 123 or it is disabled' }, { status: 403 })),
     );
 
     render(<PlaceFormModal {...defaultProps} />);
@@ -241,7 +244,7 @@ describe('PlaceFormModal', () => {
 
     await waitFor(() => {
       expect(addToast).toHaveBeenCalledWith(
-        expect.stringMatching(/search failed/i),
+        expect.stringMatching(/Places API \(New\) has not been used/i),
         'error',
         undefined,
       );
diff --git a/client/src/components/Planner/PlaceFormModal.tsx b/client/src/components/Planner/PlaceFormModal.tsx
index ae70fa61..fc76fb79 100644
--- a/client/src/components/Planner/PlaceFormModal.tsx
+++ b/client/src/components/Planner/PlaceFormModal.tsx
@@ -10,6 +10,7 @@ import { Search, Paperclip, X, AlertTriangle, Loader2 } from 'lucide-react'
 import { useTranslation } from '../../i18n'
 import CustomTimePicker from '../shared/CustomTimePicker'
 import { DEFAULT_FORM, isGoogleMapsUrl, type PlaceFormData } from './PlaceFormModal.helpers'
+import { getApiErrorMessage } from '../../utils/apiError'
 import type { Place, Category, Assignment } from '../../types'
 
 // The submit payload mirrors the form, but lat/lng are parsed to numbers and
@@ -188,7 +189,7 @@ function usePlaceFormModal(props: PlaceFormModalProps) {
       const result = await mapsApi.search(mapsSearch, language)
       setMapsResults(result.places || [])
     } catch (err: unknown) {
-      toast.error(t('places.mapsSearchError'))
+      toast.error(getApiErrorMessage(err, t('places.mapsSearchError')))
     } finally {
       setIsSearchingMaps(false)
     }
@@ -228,7 +229,7 @@ function usePlaceFormModal(props: PlaceFormModalProps) {
     } catch (err) {
       console.error('Failed to fetch place details:', err)
       setMapsSearch(previousSearch)
-      toast.error(t('places.mapsSearchError'))
+      toast.error(getApiErrorMessage(err, t('places.mapsSearchError')))
     } finally {
       setIsSearchingMaps(false)
     }
diff --git a/client/src/components/Todo/TodoListPanel.tsx b/client/src/components/Todo/TodoListPanel.tsx
index f819a2a0..4ffa968b 100644
--- a/client/src/components/Todo/TodoListPanel.tsx
+++ b/client/src/components/Todo/TodoListPanel.tsx
@@ -222,7 +222,7 @@ export default function TodoListPanel({ tripId, items, addItemSignal = 0 }: { tr
       )}
       {isAddingNew && !selectedItem && !isMobile && ReactDOM.createPortal(
         <div onClick={e => { if (e.target === e.currentTarget) setIsAddingNew(false) }}
-          className="modal-backdrop"
+          className="trek-modal-backdrop"
           style={{ position: 'fixed', inset: 0, zIndex: 1000, background: 'rgba(15,23,42,0.5)', display: 'flex', justifyContent: 'center', alignItems: 'flex-start', paddingTop: 'calc(var(--nav-h) + 60px)', paddingBottom: 40 }}>
           <div style={{ width: 'min(520px, 92vw)', maxHeight: 'calc(100vh - var(--nav-h) - 120px)', overflow: 'auto', borderRadius: 16, boxShadow: '0 20px 60px rgba(0,0,0,0.25)' }}
             ref={el => { if (el) { const child = el.firstElementChild as HTMLElement; if (child) { child.style.width = '100%'; child.style.borderLeft = 'none'; child.style.borderRadius = '16px' } } }}>
@@ -240,7 +240,7 @@ export default function TodoListPanel({ tripId, items, addItemSignal = 0 }: { tr
       )}
       {isAddingNew && !selectedItem && isMobile && ReactDOM.createPortal(
         <div onClick={e => { if (e.target === e.currentTarget) setIsAddingNew(false) }}
-          className="modal-backdrop"
+          className="trek-modal-backdrop"
           style={{ position: 'fixed', inset: 0, zIndex: 1000, background: 'rgba(0,0,0,0.4)', display: 'flex', justifyContent: 'center', alignItems: 'flex-end', paddingBottom: 'var(--bottom-nav-h)' }}>
           <div style={{ width: '100%', maxHeight: '85vh', borderRadius: '16px 16px 0 0', overflow: 'auto' }}
             ref={el => { if (el) { const child = el.firstElementChild as HTMLElement; if (child) { child.style.width = '100%'; child.style.borderLeft = 'none'; child.style.borderRadius = '16px 16px 0 0' } } }}>
diff --git a/client/src/components/Trips/TripFormModal.test.tsx b/client/src/components/Trips/TripFormModal.test.tsx
index ed5bbac9..6ede18b7 100644
--- a/client/src/components/Trips/TripFormModal.test.tsx
+++ b/client/src/components/Trips/TripFormModal.test.tsx
@@ -260,7 +260,9 @@ describe('TripFormModal', () => {
         items: [{ type: 'image/png', getAsFile: () => file }],
       },
     });
-    expect(mockCreateObjectURL).toHaveBeenCalledWith(file);
+    // Cover selection now normalizes the file (HEIC -> JPEG) before previewing, so the
+    // createObjectURL call lands a microtask later; a non-HEIC file passes through unchanged.
+    await waitFor(() => expect(mockCreateObjectURL).toHaveBeenCalledWith(file));
 
     Object.defineProperty(URL, 'createObjectURL', { writable: true, configurable: true, value: original });
   });
diff --git a/client/src/components/Trips/TripFormModal.tsx b/client/src/components/Trips/TripFormModal.tsx
index ef1a528a..7fe17302 100644
--- a/client/src/components/Trips/TripFormModal.tsx
+++ b/client/src/components/Trips/TripFormModal.tsx
@@ -8,6 +8,7 @@ import { useCanDo } from '../../store/permissionsStore'
 import { useToast } from '../shared/Toast'
 import { useTranslation } from '../../i18n'
 import { CustomDatePicker } from '../shared/CustomDateTimePicker'
+import { normalizeImageFile } from '../../utils/convertHeic'
 import type { Trip } from '../../types'
 import type { TripCreateRequest } from '@trek/shared'
 
@@ -141,15 +142,17 @@ export default function TripFormModal({ isOpen, onClose, onSave, trip, onCoverUp
     }
   }
 
-  const handleCoverSelect = (file) => {
+  const handleCoverSelect = async (file) => {
     if (!file) return
+    // HEIC/HEIF from iOS can't be rendered or stored as-is — convert to JPEG first
+    const normalized = await normalizeImageFile(file)
     if (isEditing && trip?.id) {
       // Existing trip: upload immediately
-      uploadCoverNow(file)
+      uploadCoverNow(normalized)
     } else {
       // New trip: stage for upload after creation
-      setPendingCoverFile(file)
-      setCoverPreview(URL.createObjectURL(file))
+      setPendingCoverFile(normalized)
+      setCoverPreview(URL.createObjectURL(normalized))
     }
   }
 
diff --git a/client/src/components/shared/Modal.test.tsx b/client/src/components/shared/Modal.test.tsx
index 261b375a..be49756f 100644
--- a/client/src/components/shared/Modal.test.tsx
+++ b/client/src/components/shared/Modal.test.tsx
@@ -56,7 +56,7 @@ describe('Modal', () => {
 
   it('FE-COMP-MODAL-008: clicking the backdrop calls onClose', () => {
     render(<Modal isOpen={true} onClose={onClose}><p>inner</p></Modal>);
-    const backdrop = document.querySelector('.modal-backdrop') as HTMLElement;
+    const backdrop = document.querySelector('.trek-modal-backdrop') as HTMLElement;
     // Simulate mousedown then click on the backdrop itself
     fireEvent.mouseDown(backdrop, { target: backdrop });
     fireEvent.click(backdrop);
diff --git a/client/src/components/shared/Modal.tsx b/client/src/components/shared/Modal.tsx
index 48d97257..14033088 100644
--- a/client/src/components/shared/Modal.tsx
+++ b/client/src/components/shared/Modal.tsx
@@ -51,7 +51,7 @@ export default function Modal({
 
   return ReactDOM.createPortal(
     <div
-      className="fixed inset-0 z-[200] flex items-start sm:items-center justify-center px-4 modal-backdrop trek-backdrop-enter bg-[rgba(15,23,42,0.5)]"
+      className="fixed inset-0 z-[200] flex items-start sm:items-center justify-center px-4 trek-modal-backdrop trek-backdrop-enter bg-[rgba(15,23,42,0.5)]"
       style={{ paddingTop: 70, paddingBottom: 'calc(20px + var(--bottom-nav-h))', overflow: 'hidden' }}
       onMouseDown={e => { mouseDownTarget.current = e.target }}
       onClick={e => {
diff --git a/client/src/index.css b/client/src/index.css
index 09b16614..9eb16666 100644
--- a/client/src/index.css
+++ b/client/src/index.css
@@ -734,7 +734,7 @@ img[alt="TREK"] {
 .dark .min-h-screen { background-color: var(--bg-primary) !important; }
 
 /* Modal-Hintergrund */
-.dark .modal-backdrop { background: rgba(0,0,0,0.6); }
+.dark .trek-modal-backdrop { background: rgba(0,0,0,0.6); }
 
 /* ── Dark: Fallback für Komponenten die noch nicht auf CSS-Variablen umgestellt sind ── */
 .dark {
@@ -766,8 +766,8 @@ img[alt="TREK"] {
   animation: slide-out-right 0.3s ease-in forwards;
 }
 
-/* Modal-Hintergrund */
-.modal-backdrop {
+/* Modal-Hintergrund (eigener Namespace, sonst blenden Content-Blocker .modal-backdrop aus) */
+.trek-modal-backdrop {
   backdrop-filter: blur(4px);
 }
 
diff --git a/client/src/pages/atlas/useAtlas.ts b/client/src/pages/atlas/useAtlas.ts
index 6e5f2422..2fef96ed 100644
--- a/client/src/pages/atlas/useAtlas.ts
+++ b/client/src/pages/atlas/useAtlas.ts
@@ -141,7 +141,10 @@ export function useAtlas() {
         for (const f of geo.features) {
           const a2 = f.properties?.ISO_A2
           const a3 = f.properties?.ADM0_A3 || f.properties?.ISO_A3
-          if (a2 && a3 && a2 !== '-99' && a3 !== '-99' && !A2_TO_A3[a2]) {
+          // Only real 2-letter ISO codes: natural-earth uses subdivision-style
+          // values like "CN-TW" for Taiwan, which would otherwise overwrite the
+          // legitimate TWN->TW reverse mapping and break the country (#1049).
+          if (a2 && a3 && a2.length === 2 && a2 !== '-99' && a3 !== '-99' && !A2_TO_A3[a2]) {
             A2_TO_A3[a2] = a3
           }
         }
@@ -619,7 +622,7 @@ export function useAtlas() {
     try {
       const result = await mapsApi.search(bucketSearch, language)
       setBucketSearchResults(result.places || [])
-    } catch {} finally { setBucketSearching(false) }
+    } catch (err) { console.error('Bucket-list place search failed:', err) } finally { setBucketSearching(false) }
   }
 
   const handleSelectBucketPoi = (result: any) => {
diff --git a/client/src/utils/apiError.ts b/client/src/utils/apiError.ts
new file mode 100644
index 00000000..181cb42a
--- /dev/null
+++ b/client/src/utils/apiError.ts
@@ -0,0 +1,9 @@
+/**
+ * Pulls the server-provided error string out of an axios-style error so the UI can
+ * surface the real reason (e.g. a Google Places API message such as "Places API (New)
+ * has not been used in project … or it is disabled") instead of a generic fallback.
+ */
+export function getApiErrorMessage(err: unknown, fallback: string): string {
+  const message = (err as { response?: { data?: { error?: unknown } } })?.response?.data?.error
+  return typeof message === 'string' && message.trim() ? message : fallback
+}
diff --git a/server/src/nest/places/places.controller.ts b/server/src/nest/places/places.controller.ts
index 744815c6..7e930e3e 100644
--- a/server/src/nest/places/places.controller.ts
+++ b/server/src/nest/places/places.controller.ts
@@ -117,7 +117,7 @@ export class PlacesController {
     if (!importWaypoints && !importRoutes && !importTracks) {
       throw new HttpException({ error: 'No import types selected' }, 400);
     }
-    const result = this.places.importGpx(tripId, file.buffer, { importWaypoints, importRoutes, importTracks });
+    const result = this.places.importGpx(tripId, file.buffer, { importWaypoints, importRoutes, importTracks, defaultName: file.originalname });
     if (!result) {
       throw new HttpException({ error: 'No matching places found in GPX file' }, 400);
     }
diff --git a/server/src/nest/places/places.service.ts b/server/src/nest/places/places.service.ts
index 909f8483..eedf767d 100644
--- a/server/src/nest/places/places.service.ts
+++ b/server/src/nest/places/places.service.ts
@@ -52,7 +52,11 @@ export class PlacesService {
     return svc.deletePlacesMany(tripId, ids);
   }
 
-  importGpx(tripId: string, buffer: Buffer, opts: { importWaypoints: boolean; importRoutes: boolean; importTracks: boolean }) {
+  importGpx(
+    tripId: string,
+    buffer: Buffer,
+    opts: { importWaypoints: boolean; importRoutes: boolean; importTracks: boolean; defaultName?: string },
+  ) {
     return svc.importGpx(tripId, buffer, opts);
   }
 
diff --git a/server/src/services/atlasService.ts b/server/src/services/atlasService.ts
index 1620137a..c9cf091c 100644
--- a/server/src/services/atlasService.ts
+++ b/server/src/services/atlasService.ts
@@ -534,13 +534,18 @@ const geocodingInFlight = new Set<number>();
 
 const regionCache = new Map<string, RegionInfo | null>();
 
-async function reverseGeocodeRegion(lat: number, lng: number): Promise<RegionInfo | null> {
-  const key = roundKey(lat, lng);
-  if (regionCache.has(key)) return regionCache.get(key)!;
+// A zoom-8 reverse geocode of a GB place only resolves to the constituent country
+// (England/Scotland/Wales/Northern Ireland). Natural Earth's admin-1 polygons for GB
+// are counties and boroughs, so those four codes match no polygon and never highlight.
+const GB_CONSTITUENT_CODES = new Set(['GB-ENG', 'GB-SCT', 'GB-WLS', 'GB-NIR']);
+
+// Returns the OSM address object, {} for an "ok but empty" response (so it is cached as
+// a definitive miss), or null for a transient failure (so it is retried next time).
+async function fetchNominatimAddress(lat: number, lng: number, zoom: number): Promise<Record<string, string> | null> {
   await throttleNominatim();
   try {
     const res = await fetch(
-      `https://nominatim.openstreetmap.org/reverse?lat=${lat}&lon=${lng}&format=json&zoom=8&accept-language=en`,
+      `https://nominatim.openstreetmap.org/reverse?lat=${lat}&lon=${lng}&format=json&zoom=${zoom}&accept-language=en`,
       {
         headers: { 'User-Agent': 'TREK Travel Planner (https://github.com/mauriceboe/TREK)' },
         signal: AbortSignal.timeout(10_000),
@@ -548,27 +553,52 @@ async function reverseGeocodeRegion(lat: number, lng: number): Promise<RegionInf
     );
     if (!res.ok) return null;
     const data = await res.json() as { address?: Record<string, string> };
-    const countryCode = data.address?.country_code?.toUpperCase() || null;
-    // Try finest ISO level first (lvl6 = departments/provinces), then lvl5, then lvl4 (states/regions)
-    let regionCode = data.address?.['ISO3166-2-lvl6'] || data.address?.['ISO3166-2-lvl5'] || data.address?.['ISO3166-2-lvl4'] || null;
-    // Normalize: FR-75C → FR-75 (strip trailing letter suffixes for GeoJSON compatibility)
-    if (regionCode && /^[A-Z]{2}-\d+[A-Z]$/i.test(regionCode)) {
-      regionCode = regionCode.replace(/[A-Z]$/i, '');
-    }
-    const regionName = data.address?.state || data.address?.province || data.address?.region || data.address?.county || data.address?.city || null;
-    if (!countryCode || !regionName) { regionCache.set(key, null); return null; }
-    const info: RegionInfo = {
-      country_code: countryCode,
-      region_code: regionCode || `${countryCode}-${regionName.substring(0, 3).toUpperCase()}`,
-      region_name: regionName,
-    };
-    regionCache.set(key, info);
-    return info;
+    return data.address ?? {};
   } catch {
     return null;
   }
 }
 
+function buildRegionInfo(address: Record<string, string>, preferFinest: boolean): RegionInfo | null {
+  const countryCode = address.country_code?.toUpperCase() || null;
+  // Coarse path (almost every country) lands on the admin-1 level that matches Natural
+  // Earth directly; the finest path is used only to rescue codes that are too broad.
+  let regionCode = preferFinest
+    ? (address['ISO3166-2-lvl8'] || address['ISO3166-2-lvl7'] || address['ISO3166-2-lvl6'] || address['ISO3166-2-lvl5'] || null)
+    : (address['ISO3166-2-lvl6'] || address['ISO3166-2-lvl5'] || address['ISO3166-2-lvl4'] || null);
+  // Normalize: FR-75C → FR-75 (strip trailing letter suffixes for GeoJSON compatibility)
+  if (regionCode && /^[A-Z]{2}-\d+[A-Z]$/i.test(regionCode)) {
+    regionCode = regionCode.replace(/[A-Z]$/i, '');
+  }
+  const regionName = preferFinest
+    ? (address.city || address.county || address.state_district || address.borough || address.state || address.province || address.region || null)
+    : (address.state || address.province || address.region || address.county || address.city || null);
+  if (!countryCode || !regionName) return null;
+  return {
+    country_code: countryCode,
+    region_code: regionCode || `${countryCode}-${regionName.substring(0, 3).toUpperCase()}`,
+    region_name: regionName,
+  };
+}
+
+async function reverseGeocodeRegion(lat: number, lng: number): Promise<RegionInfo | null> {
+  const key = roundKey(lat, lng);
+  if (regionCache.has(key)) return regionCache.get(key)!;
+  const address = await fetchNominatimAddress(lat, lng, 8);
+  if (!address) return null; // transient failure — leave uncached so a later call retries
+  let info = buildRegionInfo(address, false);
+  // GB constituent-country codes map to no admin-1 polygon, so re-resolve them at a finer
+  // zoom where Nominatim exposes the county/borough code (GB-LND, GB-MAN, GB-CON, …) that
+  // the polygons actually carry.
+  if (info && info.country_code === 'GB' && GB_CONSTITUENT_CODES.has(info.region_code)) {
+    const finerAddress = await fetchNominatimAddress(lat, lng, 10);
+    const finer = finerAddress ? buildRegionInfo(finerAddress, true) : null;
+    if (finer && !GB_CONSTITUENT_CODES.has(finer.region_code)) info = finer;
+  }
+  regionCache.set(key, info);
+  return info;
+}
+
 export async function getVisitedRegions(userId: number): Promise<{ regions: Record<string, { code: string; name: string; placeCount: number }[]> }> {
   const trips = getUserTrips(userId);
   const tripIds = trips.map(t => t.id);
diff --git a/server/src/services/placeService.ts b/server/src/services/placeService.ts
index d5dd7810..ed91c3eb 100644
--- a/server/src/services/placeService.ts
+++ b/server/src/services/placeService.ts
@@ -346,6 +346,8 @@ export interface GpxImportOptions {
   importWaypoints?: boolean;
   importRoutes?: boolean;
   importTracks?: boolean;
+  /** Source filename used to name unnamed routes/tracks (keeps multiple imports distinct). */
+  defaultName?: string;
 }
 
 export interface KmlImportOptions {
@@ -354,7 +356,7 @@ export interface KmlImportOptions {
 }
 
 export function importGpx(tripId: string, fileBuffer: Buffer, opts: GpxImportOptions = {}) {
-  const { importWaypoints = true, importRoutes = true, importTracks = true } = opts;
+  const { importWaypoints = true, importRoutes = true, importTracks = true, defaultName } = opts;
 
   const parsed = gpxParser.parse(fileBuffer.toString('utf-8'));
   const gpx = parsed?.gpx;
@@ -363,6 +365,20 @@ export function importGpx(tripId: string, fileBuffer: Buffer, opts: GpxImportOpt
   const str = (v: unknown) => (v != null ? String(v).trim() : null);
   const num = (v: unknown) => { const n = parseFloat(String(v)); return isNaN(n) ? null : n; };
 
+  // Routes and tracks rarely carry their own <name>. Without one they all fall back to the
+  // same generic label, so name-based dedup drops every import after the first. Derive a
+  // base from the source filename (the requested behaviour) and suffix an index so multiple
+  // geometries from one file stay distinct.
+  const rawName = str(defaultName);
+  const baseName = rawName ? rawName.replace(/\.[^.]+$/, '').trim() || rawName : null;
+  let geoSeq = 0;
+  const geoName = (explicit: string | null, fallback: string): string => {
+    if (explicit) return explicit;
+    geoSeq++;
+    const base = baseName || fallback;
+    return geoSeq === 1 ? base : `${base} ${geoSeq}`;
+  };
+
   type WaypointEntry = { name: string; lat: number; lng: number; description: string | null; routeGeometry?: string };
   const waypoints: WaypointEntry[] = [];
 
@@ -385,7 +401,7 @@ export function importGpx(tripId: string, fileBuffer: Buffer, opts: GpxImportOpt
       if (pts.length === 0) continue;
       const hasAllEle = pts.every(p => p.ele !== null);
       const routeGeometry = pts.map(p => hasAllEle ? [p.lat, p.lng, p.ele] : [p.lat, p.lng]);
-      waypoints.push({ lat: pts[0].lat, lng: pts[0].lng, name: str(rte.name) || 'GPX Route', description: str(rte.desc), routeGeometry: JSON.stringify(routeGeometry) });
+      waypoints.push({ lat: pts[0].lat, lng: pts[0].lng, name: geoName(str(rte.name), 'GPX Route'), description: str(rte.desc), routeGeometry: JSON.stringify(routeGeometry) });
     }
   }
 
@@ -405,7 +421,7 @@ export function importGpx(tripId: string, fileBuffer: Buffer, opts: GpxImportOpt
       const start = trackPoints[0];
       const hasAllEle = trackPoints.every(p => p.ele !== null);
       const routeGeometry = trackPoints.map(p => hasAllEle ? [p.lat, p.lng, p.ele] : [p.lat, p.lng]);
-      waypoints.push({ lat: start.lat, lng: start.lng, name: str(trk.name) || 'GPX Track', description: str(trk.desc), routeGeometry: JSON.stringify(routeGeometry) });
+      waypoints.push({ lat: start.lat, lng: start.lng, name: geoName(str(trk.name), 'GPX Track'), description: str(trk.desc), routeGeometry: JSON.stringify(routeGeometry) });
     }
   }
 
diff --git a/server/src/services/tripService.ts b/server/src/services/tripService.ts
index 5d024b7e..63ae51b7 100644
--- a/server/src/services/tripService.ts
+++ b/server/src/services/tripService.ts
@@ -122,12 +122,26 @@ export function generateDays(tripId: number | bigint | string, startDate: string
     del.run(dated[i].id);
   }
 
-  // Any remaining unused dateless days: keep as dateless, just renumber.
+  // Any remaining unused dateless days: drop the empty placeholders so day_count
+  // reflects the dated range, but keep ones that still hold content (assignments,
+  // notes, accommodations) — mirrors the dateless-path trimming above (#1083).
   // Base must be max(targetDates.length, dated.length) to avoid colliding with
   // positives already assigned by the main loop or the overflow loop above.
+  const isEmptyDay = db.prepare(
+    `SELECT NOT EXISTS (SELECT 1 FROM day_assignments da WHERE da.day_id = @id)
+          AND NOT EXISTS (SELECT 1 FROM day_notes dn WHERE dn.day_id = @id)
+          AND NOT EXISTS (SELECT 1 FROM day_accommodations dac WHERE dac.start_day_id = @id OR dac.end_day_id = @id) AS empty`
+  );
   const maxAssigned = Math.max(targetDates.length, dated.length);
+  let keptDateless = 0;
   for (let i = datelessIdx; i < dateless.length; i++) {
-    setDayNumber.run(maxAssigned + (i - datelessIdx) + 1, dateless[i].id);
+    const empty = (isEmptyDay.get({ id: dateless[i].id }) as { empty: number }).empty;
+    if (empty) {
+      del.run(dateless[i].id);
+    } else {
+      setDayNumber.run(maxAssigned + keptDateless + 1, dateless[i].id);
+      keptDateless++;
+    }
   }
 
   // Final renumber to compact and eliminate any gaps/negatives
diff --git a/server/tests/unit/services/atlasService.test.ts b/server/tests/unit/services/atlasService.test.ts
index 83282b3d..c709105d 100644
--- a/server/tests/unit/services/atlasService.test.ts
+++ b/server/tests/unit/services/atlasService.test.ts
@@ -505,4 +505,33 @@ describe('getVisitedRegions', () => {
     const codes = result.regions['FR'].map((r: any) => r.code);
     expect(codes).toContain('FR-75');
   });
+
+  it('ATLAS-UNIT-021: GB places resolving to a constituent country are re-resolved to the finer admin-1 code', async () => {
+    vi.useFakeTimers();
+    // A zoom-8 lookup only yields the constituent country (GB-ENG); the zoom-10 lookup
+    // exposes the borough code (GB-MAN) that Natural Earth's polygons actually carry.
+    vi.stubGlobal('fetch', vi.fn().mockImplementation((url: string) => Promise.resolve({
+      ok: true,
+      json: async () => ({
+        address: url.includes('zoom=10')
+          ? { country_code: 'gb', 'ISO3166-2-lvl8': 'GB-MAN', city: 'Manchester', state: 'England', 'ISO3166-2-lvl4': 'GB-ENG' }
+          : { country_code: 'gb', 'ISO3166-2-lvl4': 'GB-ENG', state: 'England' },
+      }),
+    })));
+
+    const { user } = createUser(testDb);
+    const trip = createTrip(testDb, user.id, { title: 'Manchester Trip' });
+    insertPlaceWithCoords(testDb, trip.id, 'Old Trafford', 53.4631, -2.2913);
+
+    await getVisitedRegions(user.id);
+    await vi.runAllTimersAsync();
+    const result = await getVisitedRegions(user.id);
+
+    expect(result.regions['GB']).toBeDefined();
+    const codes = result.regions['GB'].map((r: any) => r.code);
+    expect(codes).toContain('GB-MAN');
+    expect(codes).not.toContain('GB-ENG');
+
+    vi.useRealTimers();
+  });
 });
diff --git a/server/tests/unit/services/placeService.test.ts b/server/tests/unit/services/placeService.test.ts
index 00fb6920..5bec43d7 100644
--- a/server/tests/unit/services/placeService.test.ts
+++ b/server/tests/unit/services/placeService.test.ts
@@ -346,6 +346,39 @@ describe('importGpx', () => {
     const result = importGpx(String(trip.id), gpx);
     expect(result).toBeNull();
   });
+
+  it('PLACE-SVC-037 — multiple unnamed tracks in one file get distinct names instead of collapsing to one', () => {
+    const { user } = createUser(testDb);
+    const trip = createTrip(testDb, user.id);
+    const gpx = Buffer.from(`<?xml version="1.0"?><gpx version="1.1">
+      <trk><trkseg>
+        <trkpt lat="48.8566" lon="2.3522"></trkpt>
+        <trkpt lat="48.8570" lon="2.3530"></trkpt>
+      </trkseg></trk>
+      <trk><trkseg>
+        <trkpt lat="40.0000" lon="-3.0000"></trkpt>
+        <trkpt lat="40.1000" lon="-3.1000"></trkpt>
+      </trkseg></trk>
+    </gpx>`);
+    const result = importGpx(String(trip.id), gpx) as any;
+    expect(result.places).toHaveLength(2);
+    const names = result.places.map((p: any) => p.name);
+    expect(new Set(names).size).toBe(2);
+  });
+
+  it('PLACE-SVC-038 — unnamed tracks fall back to the source filename', () => {
+    const { user } = createUser(testDb);
+    const trip = createTrip(testDb, user.id);
+    const gpx = Buffer.from(`<?xml version="1.0"?><gpx version="1.1">
+      <trk><trkseg>
+        <trkpt lat="48.8566" lon="2.3522"></trkpt>
+        <trkpt lat="48.8570" lon="2.3530"></trkpt>
+      </trkseg></trk>
+    </gpx>`);
+    const result = importGpx(String(trip.id), gpx, { defaultName: 'morning-hike.gpx' }) as any;
+    expect(result.places).toHaveLength(1);
+    expect(result.places[0].name).toBe('morning-hike');
+  });
 });
 
 // ── importGoogleList ──────────────────────────────────────────────────────────
diff --git a/server/tests/unit/services/tripService.test.ts b/server/tests/unit/services/tripService.test.ts
index 795dbcb2..a4411b4d 100644
--- a/server/tests/unit/services/tripService.test.ts
+++ b/server/tests/unit/services/tripService.test.ts
@@ -242,6 +242,33 @@ describe('generateDays', () => {
     const nums = daysAfter.map(d => d.day_number).sort((a, b) => a - b);
     expect(nums).toEqual([1, 2, 3, 4, 5]);
   });
+
+  it('TRIP-SVC-017: switching a dateless trip to a shorter dated range drops empty leftover days but keeps ones with content (#1083)', () => {
+    const { user } = createUser(testDb);
+    // A 7-day trip, then cleared to dateless placeholders (day_count = 7).
+    const trip = createTrip(testDb, user.id, { start_date: '2025-12-01', end_date: '2025-12-07' });
+    generateDays(trip.id, null, null);
+    const dateless = getDays(trip.id);
+    expect(dateless).toHaveLength(7);
+    expect(dateless.every(d => d.date === null)).toBe(true);
+
+    // Give the LAST dateless day real content so it must be preserved.
+    const place = createPlace(testDb, trip.id);
+    const assignment = createDayAssignment(testDb, dateless[6].id, place.id);
+
+    // Now set an explicit 2-day range. The first two dateless days are reused for
+    // the dates; the four empty leftovers must be removed, the one with content kept.
+    generateDays(trip.id, '2026-01-10', '2026-01-11');
+
+    const daysAfter = getDays(trip.id);
+    const dated = daysAfter.filter(d => d.date !== null);
+    const stillDateless = daysAfter.filter(d => d.date === null);
+    expect(dated.map(d => d.date)).toEqual(['2026-01-10', '2026-01-11']);
+    // day_count is COUNT(*) FROM days: 2 dated + 1 content-bearing dateless = 3 (not the stale 7)
+    expect(daysAfter).toHaveLength(3);
+    expect(stillDateless).toHaveLength(1);
+    expect(getAssignments(stillDateless[0].id)[0].id).toBe(assignment.id);
+  });
 });
 
 describe('exportICS', () => {