Photographer's NAS Migration Guide: Windows to Mac with Synology

This guide documents a complete storage architecture and migration plan for analog and digital photographers moving from a Windows workflow to macOS, using a Synology NAS as the central hub. It covers Lightroom Classic catalog migration (including a critical macOS bug and its workaround), Synology Drive integration, Premiere Pro video workflow, Synology Photos, and a three-tier backup strategy.

The architecture was developed for a medium format film photographer using Lightroom Classic, an Epson V800 flatbed scanner, and Negative Lab Pro — but the principles apply to any NAS-centric photography workflow.

Hardware: MacBook Air M5 / 1TB SSD / 32GB RAM + Synology NAS (2× 8TB)

Principle: NAS as private cloud and source of truth. Synology Drive syncs to Mac (on-demand or full). Cloud as safety net.

Date: March 2026

Architecture Summary

MacBook Local Structure

~/Pictures/
├── Lightroom/
│   └── Catalog/                            ← .lrcat (local only — NOT in Synology Drive)
├── Exports/                                ← LR export landing zone (temp)

[macOS-assigned Synology Drive folder]/     ← System-controlled location
├── Photography/
│   ├── RAW Files/                          ← "Local RAW Files" — Lightroom points here
│   │   ├── Pentacon Six TL/
│   │   │   ├── R37-0000/
│   │   │   └── ...
│   │   ├── Zeiss Ikon Ikonta/
│   │   ├── Zeiss Ikon Contina IIa/
│   │   └── Holga 120 GCFN/
│   ├── Projects/                           ← Zine/publication exports (your work)
│   ├── SAAL Print/                         ← Curated exports for printing
│   ├── Collected Zines/              ← Collected zines (not your work)
│   └── Lightroom Backup/                   ← LR catalog backups
├── Videos/                                 ← On-demand: NAS /Videos/
├── Premiere Projects/                      ← On-demand: NAS /Premiere Projects/
├── Blog/                                   ← Bidirectional: NAS /Drive/Blog/
├── Documents/                              ← Bidirectional: NAS /Drive/Documents/
└── Light Exports/                          ← Bidirectional: NAS /Drive/Light Exports/

No OneDrive client on Mac. O365 installed for apps only.

The Synology Drive folder path will be determined by macOS during setup. Note this path — you’ll need it for the Lightroom folder remapping step.

NAS Directory Structure

/homes/[username]/
├── Photography/                            ← ANALOG FILM WORKFLOW (separate from Synology Photos)
│   ├── RAW Files/                          ← Film scan masters
│   │   ├── Pentacon Six TL/
│   │   │   ├── R37-0000/                   ← Roll#-LabNr (roll first, lab for cross-ref)
│   │   │   │   ├── Pentacon Six R37 001-positive.tif
│   │   │   │   ├── ...
│   │   │   │   └── R37.pdf                 ← Contact sheet (stays with the roll)
│   │   │   ├── R38-0000/
│   │   │   └── ...
│   │   ├── Zeiss Ikon Ikonta/
│   │   ├── Zeiss Ikon Contina IIa/
│   │   └── Holga 120 GCFN/
│   ├── Projects/                           ← Publication exports (zines, blog)
│   │   ├── 2025-01-From My Front Door/
│   │   ├── 2026-03-Doors of Perception Vol 2/
│   │   └── ...
│   ├── SAAL Print/                         ← Curated exports for SAAL Digital printing
│   ├── Collected Zines/              ← Collected zines from photographer friend
│   └── Lightroom Backup/                   ← Catalog backups from LR
│
├── Photos/                                 ← Synology Photos personal space
│   ├── MobileBackup/                       ← Android auto-upload
│   │   └── [Your Phone]/DCIM/Camera/YYYY/
│   ├── 2025-04 Spring Trip Oregon/
│   │   ├── (all photos flat — no device subfolders)
│   │   └── Edits/                          ← Selected + processed finals
│   ├── 2025-10 Arizona - Grand Canyon/
│   └── ...
│   (albums created here, shared with wife via Synology Photos)
│
├── Videos/                                 ← CONSOLIDATED video archive
│   ├── 2001 City Trip/
│   ├── 2002 - Sailing Trip/
│   ├── 2005-04 Anniversary Trip Spain/
│   ├── ...
│   └── [Event Name]/
│       ├── RAW/                            ← Uncut footage by day
│       │   ├── Day 1 - YYYY-MM-DD/
│       │   └── Day 2 - YYYY-MM-DD/
│       ├── Edits/                          ← Final processed videos
│       ├── Stills/                         ← Camera photos (e.g. HDR-CX105E)
│       └── Trailers/                       ← Short clips
│
├── Premiere Projects/                      ← .prproj files (synced via Drive)
│
├── Drive/                                  ← Synology Drive sync target
│   ├── Blog/
│   ├── Documents/
│   └── Light Exports/

Sync Channels

1. Synology Drive — Sync (Photography: Mac ↔ NAS, bidirectional)

Synology Drive syncs the Photography folder between Mac and NAS. On macOS, the sync folder location is system-assigned (not customizable). Lightroom points to the RAW Files subfolder within this location.

Other Photography subfolders (SAAL Print, Projects, Lightroom Backup, Collected Zines) sync as part of the same /Photography/ sync.

Lightroom catalog (.lrcat) stays in ~/Pictures/Lightroom/Catalog/ (local only — outside the Synology Drive folder).

2. Synology Drive — On-Demand Sync (Video: Mac ↔ NAS, bidirectional)

Premiere Pro projects and video footage synced via Drive with Files On-Demand. NAS is source of truth. Files appear local but are only downloaded when opened by Premiere.

Final video exports go directly to NAS: /Videos/[Event]/Edits/. Pre-pin an event’s RAW folder locally before heavy edit sessions to avoid on-demand latency.

3. Synology Drive — Sync (Lightweight: Mac ↔ NAS, bidirectional)

Always local, no on-demand. Small files — blog content, documents, JPEG exports.

4. Synology Photos

How it works: Synology Photos indexes the personal /homes/[username]/Photos/ folder (plus the shared Photos space). Only content inside this folder is visible in Synology Photos — folders like Photography/Projects/ are outside its scope.

Mobile backup: Android auto-uploads to Photos/MobileBackup/[Your Phone]/DCIM/Camera/YYYY/

Albums: Created within Photos/, can reference any content indexed by Synology Photos. Shared with wife via album sharing.

Cloud Sync: /homes/[username]/Photos/ is pushed one-way to OneDrive — covers both event folders and MobileBackup in a single sync task.

5. Cloud Sync (NAS → OneDrive, one-way)

Pushes selected NAS folders to OneDrive as a secondary off-site backup. Two tasks only:

Not synced to OneDrive: Photography/ (analog film workflow) — too large for 1TB OneDrive, and already covered by Hyper Backup to B2.

Settings for both tasks: Sync direction “Upload local changes only”, “Don’t remove files from destination” checked (during migration), advanced consistency check enabled.

6. Hyper Backup (NAS → Backblaze B2)

Primary off-site backup for the ENTIRE NAS including film RAW masters and video RAW footage. Replaces Azure Blob Storage (phasing out due to cost). This is the backup layer that covers everything OneDrive cannot.

Lightroom Film Scanning Workflow on Mac

Scanning a new roll

1. Scan with Epson V800 + Epson Scan 2 on Mac
2. Save TIFFs to the Synology Drive folder: .../Photography/RAW Files/[Camera]/[Lab#]/
3. Synology Drive syncs new files to NAS automatically
4. Import into Lightroom from the synced RAW Files folder (no auto-adjustments)
5. Crop, NLP conversion, metadata, naming — all local, full SSD speed

Exporting from Lightroom

All exports land in ~/Pictures/Exports/ first (local temp folder), then move to their destination:

Managing local space

With 1TB SSD and on-demand sync disabled, the entire film catalog (~200 GB for 40+ rolls) fits locally. If space runs low, enable on-demand sync — Synology Drive will free local space for rolls you’re not actively editing, and re-download them when Lightroom accesses them.

Premiere Pro Video Workflow on Mac

New project

1. Import footage from camera/SD card/phone directly to NAS: /Videos/[Event]/RAW/Day 1 - YYYY-MM-DD/
2. Create Premiere project in /Premiere Projects/ on NAS (synced to Mac via Drive)
3. Open project on Mac — Synology Drive downloads .prproj and referenced RAW files on demand
4. Edit, color grade, audio mix — files cached locally at SSD speed
5. For heavy sessions: pre-pin the event’s RAW folder locally to avoid on-demand latency

Export and deliver

1. Export final video directly to NAS: /Videos/[Event]/Edits/
2. If trailers created: /Videos/[Event]/Trailers/
3. Plex Media Server auto-indexes from Videos/*/Edits/

Revisiting old projects

Open any old .prproj in Premiere — Synology Drive pulls the RAW footage on demand. No need to manually download or mount anything. When done, the local cache can be freed automatically by Drive.

Photo Folder Structure — Going Forward

New event folder structure

2026-07 Summer Trip/
├── IMG_001.jpg                             ← Phone photo
├── IMG_002.jpg                             ← Phone photo
├── Pentacon Six TL R45 003.jpg             ← Film scan export
├── ...
└── Edits/                                  ← Selected + processed finals

Legacy event folders

Leave existing device subfolders (HDR-CX105E Stills, Lumia 920, etc.) as-is. Renaming 20 years of folders risks breaking Premiere project references and Plex metadata. The old structure works — just don’t replicate it going forward.

Migration Checklist

Phase 1: Prepare NAS

• Switch Cloud Sync from bidirectional to one-way (NAS → OneDrive)
• Configure Hyper Backup to Backblaze B2
• Run initial full Hyper Backup to B2
• Keep Azure Hyper Backup running in parallel
• Move any film scan exports out of Photos/ event folders into Projects/

Phase 2: Video + Photo Consolidation (NAS runs 2× 8TB drives)

• Install new drives, expand storage pool / create new volume
• Stop Cloud Sync: Delete existing Cloud Sync tasks before moving any folders
• Videos: Create /homes/[username]/Videos/ with clean event-folder structure
• Reunite RAW footage from Adobe Premiere Projects/[event]/ back into Videos/[event]/RAW/
• Move edited finals from Plex library into Videos/[event]/Edits/
• Migrate content from video/Unsere Filme/ into Videos/
• Migrate content from Photos/OneDrive Videos/ into Videos/
• Deduplicate videos — verify no content is lost, then delete old locations
• Create /homes/[username]/Premiere Projects/ for .prproj files
• Reconfigure Plex to point at Videos/*/Edits/ (or use symlinks)
• Verify Plex indexes correctly from new location
• Photos: Move event folders from Photos/OneDrive Photos/ up into Photos/ directly
• Verify Synology Photos re-indexes automatically (confirmed: albums survive folder moves)
• Delete empty Photos/OneDrive Photos/ wrapper folder
• Photography: Move Photography/RAW Files/SAAL Print/ up to Photography/SAAL Print/
• Recreate Cloud Sync: Create new task for Photos (/home/Photos → /Photos)
• Create new task for Videos (/home/Videos → /Videos)
• Both tasks: "Upload local changes only", "Don't remove from destination" checked
• Wait for initial upload to complete
• Clean up orphaned old folders on OneDrive manually

Phase 3: Mac Setup (clean install — no Windows Migration Assistant)

Step 1: Initial Mac setup

• Browser: Install Microsoft Edge on Mac, sign in with Microsoft account — passwords, bookmarks, extensions, history sync automatically from Windows
• Install O365 apps (no OneDrive client — apps only)
• Copy any remaining local-only files from Windows to NAS before proceeding (desktop files, documents not already synced)

Step 2: Synology Drive Client — install and note the folder location

• Install Synology Drive Client on Mac (version 3.2+ required for macOS 12.3+)
• macOS will assign the sync folder location automatically — note this path (you'll need it for Lightroom remapping)
  Typically: ~/Library/CloudStorage/SynologyDrive-[NASname]/
  If the folder name appears garbled in Finder: reboot the Mac
• Configure SYNC tasks:
  — NAS /Photography/ (includes RAW Files, Projects, SAAL Print, Lightroom Backup, Collected Zines)
  — NAS /Videos/ + /Premiere Projects/ (on-demand enabled)
  — NAS /Drive/Blog/, /Drive/Documents/, /Drive/Light Exports/ (always local)
• Wait for Photography/RAW Files/ initial sync to complete (may take hours — let it finish before proceeding to Lightroom)
• Verify: spot-check that camera folders and TIFFs appear in the Synology Drive folder on Mac

Step 3: Install Lightroom Classic on Mac

• Download and install Lightroom Classic via Adobe Creative Cloud
• Launch Lightroom — it will create a new empty catalog. That's fine — you need a fresh Mac catalog
• Note the catalog location (default: ~/Pictures/Lightroom/)

Step 4: Export catalog from Windows

Two confirmed approaches — pick either one:

Option A: Export as Catalog (tested and verified)

Step 4a: On the Windows machine, for each camera folder (or all at once):

• Open Lightroom Classic on Windows
• Select the camera folder(s) you want to export in the Folders panel
• File → Export as Catalog...
• Choose a destination (e.g. NAS or USB drive — somewhere the Mac can access)
• Check "Export negative files" to include the actual TIFFs/JPEGs
• Check "Include available previews" (optional — speeds up Mac import but increases file size)
• Click Export Catalog
• Repeat per camera folder, or export the entire catalog at once

Step 5a: Import catalog into Mac Lightroom:

• On Mac, open Lightroom Classic (with the fresh empty catalog)
• File → Import from Another Catalog...
• Navigate to the exported catalog from Step 4a
• Select it and click Choose
• The import dialog shows all folders — review and confirm
• Import
• All photos, edits, color labels, rankings, metadata are immediately available — no missing file indicators because the negatives were included in the export

Step 6a: Repoint to Synology Drive location:

• In the Library module, Folders panel — you'll see the imported camera folders pointing to the export location
• Right-click the first camera folder (e.g. Pentacon Six TL) → Update Folder Location
• Navigate to the Synology Drive location → local-raw-files/Pentacon Six TL/ → click Choose
• All subfolders (roll folders) under that camera reconnect to the Drive-synced copies automatically
• Verify: edits, color labels, rankings, metadata still intact
• Repeat for each camera folder:
  — Pentacon Six TL
  — Zeiss Ikon Ikonta
  — Zeiss Ikon Contina IIa
  — Holga 120 GCFN
• Delete the exported copies — Lightroom now points to the Synology Drive versions, the export package is no longer needed

Option B: Relink on Windows first, then migrate catalog

Step 4b: On the Windows machine, prepare the catalog:

• Copy the RAW files from NAS to a local Windows folder (or any folder Lightroom can see)
• In Lightroom on Windows, right-click each camera folder → Update Folder Location → point to the local copies
• Verify all folders are connected and edits are intact
• Back up the catalog: File → Catalog Settings → Back Up Catalog (or let it back up on exit)

Step 5b: Move catalog to Mac:

• Copy the backed-up .lrcat file to the Mac (via NAS or USB drive)
• Place it in ~/Pictures/Lightroom/Catalog/
• Open Lightroom on Mac → File → Open Catalog → select the .lrcat file
• All edits, collections, metadata, color labels are in the catalog
• Photos will show as missing (the local Windows paths don't exist on Mac)

Step 6b: Repoint to Synology Drive location:

• Right-click each camera folder → Update Folder Location
• Navigate to the Synology Drive location → local-raw-files/[Camera]/ → click Choose
• Repeat for each camera folder
• Verify everything reconnects

Step 7: Verify and configure

• Color labels first: Check Metadata → Color Label Set matches Windows (fix before reviewing images)
• Open several images across different cameras/rolls — confirm edits are intact
• Check virtual copies, collections, and smart collections — all should be preserved
• Verify color labels: red = original negative, yellow = correction needed, green = good to use, blue = portfolio, purple = to print
• Lightroom will build previews in the background — let it run
• Set catalog backup schedule: Lightroom → Catalog Settings → Backup
  Set backup folder to the Synology Drive-synced Lightroom Backup folder (syncs to NAS automatically)
• Install and verify Negative Lab Pro plugin
• Test: make a small edit, export a JPEG to ~/Pictures/Exports/, confirm the full pipeline works

Step 8: Install remaining apps

• Install Epson Scan 2 (verify M-series / Apple Silicon support)
• Install Negative Lab Pro (if not done in Step 7)
• Install Premiere Pro

Phase 4: Scanning Test

• Connect Epson V800 via USB
• Confirm Epson Scan 2 runs on your macOS version
• Test full pipeline: scan → staging → LR import → NLP → export
• Confirm Drive backup picks up new scan files

Phase 5: Premiere Pro + Video Pipeline

• Open a test .prproj from NAS via Drive on-demand
• Verify RAW footage downloads on demand when timeline loads
• Test export: final video direct to /Videos/[Event]/Edits/
• Verify Plex indexes the new export
• Test pre-pinning a folder locally for heavy edit sessions
• Verify freeing local cache returns space after editing

Phase 6: Synology Photos Albums

• Create album structure for family sharing within Photos/
• Film scan exports for sharing go to Photos/YYYY-MM-DD Project Name/ (Lightroom export flow)
• Share relevant albums with wife

Phase 7: Verify Backup Tiers

• Synology Drive sync: Photography/RAW Files ↔ NAS (via system-assigned folder)
• Synology Drive on-demand: Videos + Premiere Projects syncing Mac ↔ NAS
• Synology Drive sync: Blog/Docs/Light Exports syncing Mac ↔ NAS
• Cloud Sync: NAS → OneDrive one-way active (Photos + Videos tasks)
• Hyper Backup: NAS → B2 completing successfully
• Test: partial restore from B2
• After 30-60 days parallel: evaluate cutting Azure

Phase 8: Decommission Windows

• All Lightroom edits accessible on Mac
• All video projects openable via Drive on-demand
• All sync/backup channels verified
• Stop OneDrive on Windows (not before — you still depend on it until Mac is fully set up)
• Scan Windows machine for any local-only files not yet on NAS (Desktop, Downloads, app data)
• Copy anything found to NAS
• Keep Windows machine powered on but offline for 30 days as safety net
• Final verification, then retire

Epson V800 on macOS

Epson Scan 2 is available for macOS. Apple Silicon (M-series): verify native or Rosetta 2 support before decommissioning Windows. USB connection: no compatibility issues expected. Negative Lab Pro works natively on Mac Lightroom Classic. DigitaLIZA holder is hardware — no OS dependency.

Naming Convention Reference

Published March 2026 by Henry. Based on a real migration from Windows 11 to macOS with Synology NAS. All personal identifiers anonymized. Camera names, zine titles, and workflow details are real.

If you find value in my content, consider supporting me with a virtual coffee or a beer.