Hello all.
Using some of the previous comments I came up with a method that’ll ensure ‘missing’ photos, that are currently represented as ‘Uploading x items’, are restored…
PREMISE
Use iOS Photos to hide all your photos then use OSX Photos to identify the ‘missing’ pictures.
IMPORTANT
Due to an apparent limitation regarding the number of items that may be selected within iOS Photos in one hit… follow the sequence below in order to identify all your pictures that refuse to upload to iCloud.
Read on…
ON YOUR MAC
1) Create a separate SMART Album for every year that you have photos e.g “2015”.
2) Create a separate NORMAL Album “2015 hiddens” and manually fill it with all the media contained within the 2015 Smart Album - this is necessary because iOS doesn’t directly support Smart Albums.
3) Repeat steps 1) & 2) for as many years of photos you have.
4) IMPORTANT! Allow plenty of time for a full (album) sync. between all your toys.
ON YOUR iOS DEVICE
5) Open one of your new Albums i.e ‘2015 hidden’
6) Press ‘select’
7) Press ‘select all’
8) Press the ‘share’ button
9) Select ‘Hide’ and then Confirm - ATTENTION! If Photos bums out at this stage it is because you have too many photos selected, therefore you will need to return to steps 1) & 2) and create half year Albums in order to split the selections.
ON YOUR MAC
10) Create a new SMART Album of “not hidden” media. Once updated, this Smart Album should represent all your missing content that was not hidden (step 9) on your iOS device - because they weren’t locally available to hide.
11) Highlight all photos and rotate them through 90deg. This minor edit forces OSX Photos to re-recognise the media and upload it to iCloud, you should see the bottom of screen counter beginning to reduce/show uploads (after several seconds grace period). You could also mark each photo as a Favourite (press ‘.’) but this is just belt n’braces for easily finding all your rotated photos a later date.
ON YOUR iOS DEVICE
12) IMPORTANT! Allow time for everything to sync. and your previously missing photos will start appearing in your ‘2015 hidden’ album et al.
13) Once your new photos have finished arriving on your iOS toy be sure to select and hide them too. Your Mac ‘not hidden’ album will gradually diminish so this will be a double-check that you really have caught everything.
Voila, you’ve recovered everything (hopefully)!
ON YOUR MAC
14) Within your Hidden (or Favourite) album, revisit each photo and re-rotate them to normal.
15) Un-hide (and un-Favourite) your newly uploaded photos.
16) Delete your temporary Year Albums.
For those that are wandering, the Hidden photo feature is the only option available in iOS for multiple selections (‘Favourite’ won’t allow multi-selection) that will then reflect through to your main Mac library.
This was the process I eventually followed to identify an original 30 missing pictures from my library of over 16,500 items. Be sure to allow sufficient time at steps 3) & 11), it was all frustratingly slow but incredibly thorough.
Good luck. Let me know if this works for any of you - just out of interest.
p.s. All of my affected photos were of a portrait orientation…