…even though the old hardware still works just fine.

I’m almost two years retired now, and computers can still take a big bite out of my day. Today’s exercise in spinning my wheels trying to get things work comes courtesy of Apple. No surprise there. It just works…except when it doesn’t.

Apple really Really wants you to keep up to date on not just their software but the hardware it runs on too. And the longer you delay buying their latest and greatest hardware, the more you find that out. And I’m still on some very old Apple hardware, because I need to stay on a very old version of MacOS. And I need to do that, because Adobe makes you rent their software now, instead of offering upgrades. I use the Macs almost exclusively in the art room for my photography and scanned in artwork from the drafting table, and I won’t rent their software for the same reason I don’t rent my brushes, pens, charcoal sticks and the drafting table.

And especially after Adobe screwed me out of 850 for the Windows version of Photoshop that I had, and was able to use for just over two years until Adobe decided the license I had was incorrect and they remote controlled shut it off.

So I’m stuck, but slowly getting unstuck. GIMP does everything I need that Photoshop did for me. The only stickler is Lightroom, but I’m almost free of that too.

In the meantime, if you have an iPhone and you’ve been keeping up to date with the OS upgrades and security patches on that, and you have an older Mac, you are getting more and more distant from any version of iTunes you are running to sync your iPhone with. Especially your music library.

A few days ago I ordered a CD of the Jerry Goldsmith soundtrack to Logan’s Run. I have had the LP version for decades, but only realized I never got a digital version when I wanted to listen to it on the iPod and it wasn’t there. So that CD came in the mail and I put it into the art room Mac, which also holds my iTunes library, and copied it over so I could put it on the iPhone, and the iPod Classic.

No sweat right? I’ve done this hundreds of times before. Then I found the soundtrack to the new Percy Jackson TV series and bought that off the iTunes store since it isn’t currently available on CD. Now I have two albums to copy over to the iPhone and iPod.

The Percy Jackson one actually downloaded to the iPhone as well as my iTunes library. Fine. I plug the iPod into the Mac and it syncs both albums no trouble. Bear in mind this is a Much older piece of Apple hardware than the iPhone I currently have. Then I try to sync the iPhone and that’s where the trouble began.

I plug the iPhone into the Mac, and iTunes says it needs a software update before it will connect to my iPhone. Fine. I’ve seen this before, after every security patch. Apple still supports my older hardware and the older version of MacOS it’s running with security patches. But now I experience a new problem; an error message saying it cannot download the iTunes update.

So I go looking around the net and lo and behold lots of people are complaining about this happening after the most recent iOS updates. And the thing of that is Apple says it should all be compatible with the older versions of iTunes. So their solutions are to either reinstall iTunes…except the version of iTunes you need for the older MacOS isn’t available anymore, even though it’s allegedly still compatible with the current version of iOS…or reinstall the operating system. Because you really wanted to spend an entire day installing MacOS and all your apps and configurations just to copy over some music to your iPhone.

I spent an entire morning today trying this and trying that to no avail, and swearing loudly that I would never put another update on any of my Apple devices ever again. You cannot downgrade iOS…that’s Apple’s policy. Now it seems, I cannot sync my iPhone with iTunes anymore, which means I can’t back it up, in addition to not being able to sync my music library.

Eventually among the wail of pain out there I see a link to a third party program that claims to run on my Mac Pro version of MacOS, and connects to my iPhone to allow backing up, file copy and music copy from the iTunes library. So I download a copy and give it a try. There was trial version functionality which allowed me to prove it did what I needed and I finally got my music copied over. Then I bought a license for it. It wasn’t expensive and it wasn’t subscription only.

This is it. It’s called iMazing and I can verify that it works…at least on my 2010 Mac Pro and iPhone Xs running iOS 17. So now I can make backups of the iPhone and copy music files over. It isn’t automatic synchronization but I can deal with it. They say it will also let you move your music and other files to an iPod Classic, which gives me some security there because I still like that little dedicated music player.

So that was my morning today. How was yours?

[UPDATE…]  Actually…the Apple “Lightning To Thirty Pin” connector Does  provide full iPod Out integration with accessories after all. I went ahead and spent fifty bucks on one at my local Apple Store because I’d started reading enough positive reviews of it to believe it was at least worth the risk. On the one hand were the initial reviews like this CNET one which flat out says the iPod functionality is missing. On the other were comments in various support forums including Apples, which indicated that at least for some folks it was working just fine. One of these said they had a Mercedes ‘E’ Class of the same year as mine. There were plenty of others though, who said it wasn’t working at all.

So I took a chance, bought one and plugged it and the new iPhone into my Mercedes, and as it turns out, everything works just as I would expect now.  So either Apple had a change of heart, or the initial reviews got it all wrong, or more likely Apple as is its wont gave out rather limited information regarding its hardware and the media just filled it the blanks however they thought best.

So everything is working now with the new iPhone and Spirit. I have all my menus back, my playlists, the alphabetic searching through things using the dashboard keypad. It’s all there, just as it was with the 4s. Fifty bucks for the adaptor, but that’s how it rolls with Apple.

I’ll say this though. I’m noticing a much improved sound quality out of this new iPhone…even through the car stereo. Bluetooth sound is even a little better…at least as far as streaming Pandora and Internet Radio.

So…(ahem)…as to the bitter heated rant I vented below about Apple breaking things and not giving a flying fuck…

Mostly. I’m Still not happy about how Apple likes to break things. It’s a chronic problem with them. But at least this upgrade turned out to be not so disastrous as I’d initially thought. The angry rest of this  post is after the break, if you still want to read it. And I will not this: not one word from Apple in any of the support forums was ever, to my knowledge, heard. They could have made things a lot clearer regarding this adapter and maybe there wouldn’t still be so much angst out there over the new connector. I still stand by my characterization of the Apple Complaint Department. And for any iPhone or iPod accessories that won’t take the Apple  adapters because of form factor or because of other issues…well…you’re still SOL…

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