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MacPro 5.1 running Yosemite 10.10.5 and iTunes 12.8.1.3. iPad Pro, 2015 model now running 14.1.

Until the 14.1 update, the iPad was happy to transfer a folder of pictures from the Mac to the iPad via iTunes. Now, after update, iTunes gives a warning that 10.11.4 is the OS needed to let them talk. Aside from the fact that I wish I knew this prior to updating the iPad, I'd like to find a way to continue this one process.

(Note: Over the years, I've accumulated a lot of paid software, and when I loaded 10.11 to another drive to test it out, there were loads of casualties. To the point where I decided I'd keep Yosemite on my main Mac, and buy a mini when Mojave was needed, as it will be to do my taxes with TurboTax in April. The jerry-rig solution would be to use the mini to do this.)

I see software such as "Waltr" which performs such a function for audio. I'm hoping to find a method that will work for photos.

FWIW - I have math problems or images that I need to screenshot and move to the iPad into Penultimate (a sister software of Evernote). This lets me write and create an assignment I can present via Zoom or turn into a PDF post edit. The Mac screen shooting avoids the need to edit the image, VS looking at original work on the iPad and screen shooting that. The process was tedious but manageable when iTunes let me bulk transfer the images.

  • I'd love to know which apps failed between 10.10 & 10.11. I don't recall that being a difficult transition [unlike some I could mention]. Will iTunes itself not update any further? I'm stuck at 12.8.2.3 on an old El Cap Mac Pro. The 5,1 btw, will run High Sierra, or Mojave if you have an up-rated GPU. – Tetsujin Nov 11 '20 at 16:00
  • Sorry, I don't recall. It was pretty traumatic at the time, and I decided to call it quits. And until now, the only thing I needed the Mini to do was follow the OS updates for TurboTax. Which I found strange. I suppose they had their reason for needing to have such a recent OS running. It seems every year they warn to update to next OS. – JTP - Apologise to Monica Nov 11 '20 at 16:04
  • @Tetsujin - if you'd like some history and a website to help see this question. Five years ago, when I made the jump to Yosemite from Snow Leo, and stayed with it even since. – JTP - Apologise to Monica Nov 11 '20 at 16:54
  • Yes, I've used RoaringApps myself for years. Snow Leo [or Lion] to Yosemite was a jump, but Yosemite to El Cap was nothing like as disruptive. Next 'dodgy' jump is to the Sierras - both of which I thought were hideous - but then to Mojave was relatively smooth. [I actually skipped the Sierras completely, updated then rolled back.] Catalina is another dodgy jump, but we don't really have to worry about that using old cheesegraters ;) – Tetsujin Nov 11 '20 at 17:01
  • Maybe I'm confused. It's possible that SnowLeo to Yosemite was the trauma, and I dug my heels in to stay with it. A 2008 MacPro runs SnowLeo for me, and a Mini, Mojave. So my room looks like this i.stack.imgur.com/nSEG8.jpg – JTP - Apologise to Monica Nov 11 '20 at 17:08

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