I’ve got a long car ride coming up this weekend and knew I was going to need to prepare some music for the journey. Driving up to Mom’s house on Thursday evening I fortified myself with a strawberry mint lemonade from Panera, which also happens to contain 260mg of caffiene. I have to avoid coffee anytime I’m out these days because the diuretic in it tends to work all too well; I’m clearly getting old. But the music situation was also key—after awhile podcasts get boring and I need something to keep me awake. Before you ask, I’m resisting cloud services because they chew through our data plan, and I’ve got a shit-ton of music catalogued on the server downstairs.

I’d ordered a new battery for our ancient iPhone 4, which has been my primary iTunes device for years, and when I went to install the replacement the four-prong connector soldered to the motherboard snapped off neatly in my meaty fingers. So I drove up with my decommissioned iPhone 6, which I’d spent less time filling with music, and which suffers from an annoying display bug that doesn’t group music in albums together in albums.

Back at home today I went through some different hoops to try and connect it to the server in the basement, which is running OS 10.7.5 (the last one compatible) and iTunes 10 in order to add more music. Both of these date to about 2015. Predictably, the iPhone 6 was not compatible. I dicked around with trying to restore the iPhone to an earlier iOS but that went nowhere. I tried a few apps that claimed they would transfer music to the iPhone, but that went nowhere ($40 to move files off the phone, but not to move music to it. What happened to all those handy file management apps back in the days of the iPod?) Finally I hooked it up to my old work tower and found a way to get music moved over through iTunes there—but none of this should have taken this long.

I guess time has made all of my home infrastructure completely obsolete even though it’s still functional. I’m going to use the old work tower as a server now that it’s decommissioned, and eventually I’ll have to figure some other solution out—a NAS or other more modern disk storage unit. But for now, it’s still humming along down there, waiting for a 2nd gen iPod and a couple of CDs to rip.