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When this happens to me it usually is because there was some hiccup in the phone's internet connection. The way I get syncing unstuck is to kill the iPhone app (double tap the home button and swipe up the Lightroom mobile window) and restart LR mobile. if you have a good wifi connection it should now start syncing again.
Jao vdL, I have tried this several times. Even signed out, killed the app, restarted and signed back in again. It does not help at all.
The phone's hooked up to my wifi, so there's no issue with connection speed.
But even if this was related to connection speed: why have neither iCloud nor Dropbox any issues with syncing relatively fast? Speed cannot be an excuse for Adobe if their peer cloud apps are doing just fine with the same file types and sizes.
LrM started syncing eventually, BUT only while I was actively editing images in the app and extremely slowly. I was doing that for about 30 minutes and after that I realised that the first 3 images were synced.
I have a reasonably fast DSL connection, so... 3 images... really? At this rate, it will take about 12 hours to sync those 68 images - feels like something I would have been happy with 15 years ago.
At the same time, syncing files via iCloud or Dropbox seems like a flash (same file size - 15 MB - transferred in about 90 sec, i.e. you'd have synced 20 images in 30 minutes - instead of 3).
Very odd: I have now connected my iPhone to my mobile wifi (3G), and it's syncing like it should.
So it seems like a connection issue after all. Even if this workaround solves the issue for me, I cannot entirely take the blame off Adobe: syncing must be reliable, something a user of LrM should never need to worry about in any of the standard infrastructure settings. iCloud and Dropbox can do it and so should Adobe's cloud.
(And it should sync in the background - as far as I can tell, you still have to keep the iPhone awake for the sync to happen. I really don't see myself sitting next to it for 2 hours and tapping the screen every 20 secs.)
Syncing still requires permanent attendance. LrM needs a regular nudge to keep syncing. Very annoying.
Also, the little cloud symbol only occasionally shows the syncing animation, so you don't know whether it's on the job or taking another one of its extended breaks.
My "solution" was to put LrM in slideshow mode and start the slideshow. This way, LrM stayed awake and kept syncing. It's less than ideal, but it's a workaround that does the job.
I have the same problem. I bought an iPhone 7 Plus mid December and I'm able to sync (download) JPG photos within 1 minute of taking them. I took 25 + DNG (raw) photos and none of them would sync, even after waiting 2 weeks. I finally sent them to Apple Photos on my iPhone and deleted them from LR Mobile. I have 45 Mbps internet download speed and even with my iPhone next to my Apple iMac, the DNG files will not download.
Yesterday I wasted over an hour with Adobe's tech support. The support person had no knowledge of how to fix the problem and I suspect he did not even understand what the issue was. In LR Preferences, Lightroom Mobile tab, he used the "Delete All Data" feature to remove all photos from LR Mobile, then selected a collection with 4 photos to re-sync. I then took 1 JPG photo and 1 DNG photo with my iPhone. The JPG synced immediately, the DNG never synced even after waiting 2 hours.
I'm not sure what is causing this problem. After searching online, it appears others are able to upload DNG photos from LR Mobile. I'm going to try to contact Adobe support again tomorrow.