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Time to refine the the Synology sync pathways.

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277
17
Operating system
  1. macOS
Mobile operating system
  1. iOS
Hello everyone,

One of the key reasons I dove into Synology NAS a few years back was to replicate a self-hosted iCloud solution (file management aspect,) and moved away from a headless MacMini given FileFault had to be disabled for the server to boot after power failure. I have managed to achieve bits and pieces of that goal, meaning something work here and there, yet nothing that smooth and nothing close iCloud. Primary use case would be syncing files to personal NAS, with secondary use case being able to work from the NAS (as in Pages, Numbers, etc...apps that read/write to the synology NAS as if it were iCloud.

Hardware: Synology DS220+ w/DSM 7.xx (most current) w/latest iOS devices and macOS devices.

Connection:
Originally started w/Synology QuickConnect but felt too many risks and migrated to VPN. Even at its best point, this was a pain and required frequent tweaks and overhead.
• Current system for the last few years has been Tailscale w/3rd party vpn. Tailscale worked well keeping devices connected yet w/a recent update to iOS, Tailscale for iOS and the VPN service, no longer able to keep both 3rd party VPN and Tailscale concurrently connected making like a PIA always switching between the two.

Sync:
Synology Drive for iOS: worked a little BUT got tired of having to constantly sign out and back in to switch IP accounts (one for remote, another for local.) Also found some of the extra taps on a frequent basis tiring...the interface defaults to one spot and you have to keep navigating to the same location w/every use...little customization beyond Favorites. Apps won't work from here mind you, you can only export or save a copy to the NAS via Drive app share sheet.

Resilio Sync: RS overall works well with one of the highest friction points (that will never be fixed) being lack of being able to background sync, so always need to bring up RS and keep it running...right PIA (albeit there are other apps that have managed background sync'ing so not buying the RS excuse of this being 100% Apple limitation.)
Note a strong positive for RS is 'selective' sync, allowing me to not stuff up storage on the iPhone but still able to grab a file on demand when needed. Now, one of the unique gotcha's of Selective Sync is that it appears iOS file system doesn't recognize folder aliases, so if using any other app (Files, FileBrowserPro etc) you can not navigate because nothing sees the alias directory...only RS seems to recognize the alias directory.

WebDAV: Have WebDAV as backup in a pinch. This too requires switching connections based on internal or external ip and, while not idea, workable given I only hit the WebDAV option in a pinch.​
Refinement:
• Connection: If Tailscale and 3rd Party VPN won't play nice together, need a new solution. Anyone familiar w/Twingate? Will Twingate support Drive and other apps, or just services like AWS?
• Sync: Sync still remains painful, always keeping RS up font, center and active. Would love sync in the background.

Have to say that I have been overall impressed w/Synology and it has been a good journey. If the journey for the simple need of a self-hosted iCloud solution means leaving Synology I am open to that, yet little faith other options will be better suited.
• Back to headless Mini and set it up w/ Pi KVM
• Revisit to OwnCloud, NextCloud like solutions (low confidence things changed to be better suited for the needs expressed above.)

TLDR; need a secure way to access and sync with home file server w/o hassles of switching accounts or VPNs when remote. Want apps to read/write from self hosted server (the same as they do for iCloud.)
 
Thanks for posting your findings here. I'm attempting to do something similar, so I find it helpful.

Regarding your connection question, have you considered just setting up your Synology to be publicly available on the web through a custom domain and SSL certificate? That's what I do since I tend to share files with clients and friends and such. I realize the security risks with this, but I think many of them can be reasonably mitigated. You probably would rather just ditch the 3rd party VPN and connect using only Tailscale, but just thought I'd throw that out there as an option.

Any chance you figured out how to use iMazing to automatically backup your iOS devices to your Synology overnight? It appears like that's supposed to be possible, but I haven't been able to get that to work. I know I can backup a lot of individual files, but I like the idea of being able to do a full phone backup the way iCloud does backups so a full restore is pretty simple.

Are you using Resilio Sync for photos and videos, too, or are you using Synology Photos or hosting Immich for that?
 

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