Dear Geek: Frustrated Listener


I was recently on a transatlantic flight, listening to my favorite tunes on my iPhone 7 on takeoff, and I was looking forward to listening to more of them throughout the flight. Much to my surprise, once we were out over the water and out of cell range, my tunes were no longer available! Turns out that the tunes I paid good money for can only be listened to when I’m within range of a cell tower or when I’m hooked up to Wi-Fi. To add insult to injury, I found out that I also must use a portion of my available data to listen to my tunes, and when my monthly data allotment is used up, I must pony up for more data!

So my question is: How can I move some of my tunes from my iPhone 7 over to my antique, but still functional, iPod? Ah, those were the good old days, weren’t they? When you put your purchased tunes on your computer and you had control over which ones went on your iPod! Oh well, I guess that’s progress.



Frustrated Listener


Dear Frustrated Listener,

Thank you for writing in, and hope you had a great trip. Though I’m not a Mac guy, I’ll do my best to help. Usually when I write my responses, I jump back, tell a little related history, then hit the solution — bear with me.

When record stores were common, we had to go buy an 8-track, CD, cassette, or vinyl (everyone over a certain age must still miss the hissing and crackle of a vinyl record playing as much as I do). I remember creating my fair share of mixtapes, starting out for fun, then like all teenagers in the ’80s, I made some for those “someone special” girls. Fast-forward to the ’90s when Napster, a revolutionary file-sharing service came out, and digital music was available at my fingertips in an instant (not that I’m admitting to using it …). After legal battles, Napster and other similar file-sharing services shut down, but the door was cracked open with regards to the ability to instantly download music, much to the chagrin of Strawberries Records & Tapes and Tower Records. iTunes and other streaming music services began offering music online, legally. iTunes and the iPod were a perfect match. Buying music, just a singular song as opposed to an album, was incredibly convenient, and being able to carry an incredible number of songs around on a small device was revolutionary. Putting this onto an iPhone (at that point only available through AT&T, if you remember those days) and adding Internet/apps made these new smartphones nearly limitless in their ability.

Fast-forward to more now, and Apple has a service called Apple Music, which is a solution to what you are after. Apple Music is a streaming service ($9.99 a month or $14.99 a month for a family plan with up to six users). This allows you to stream and download any song in their library for offline listening. If you already have an extensive music library and don’t want to pay the subscription price, Apple has the iTunes Match service ($24.99 a year), which allows you to put your iTunes purchased songs into your iCloud, which are then available for download onto an iPhone, iPod touch, iPad, Mac, or Windows PC (up to five computers and a total of 10 devices are allowed). I feel that one of those two services is the best solution for you, and I’d recommend reading through their services online to figuring out which one is the best fit.

For readers who do not use iTunes, I’d look at Spotify, Google Play Music, and Amazon Music. The pricing is all similar, and they all have the ability to stream and/or download music for offline play.

Perhaps my favorite use of these services (besides playlists for car rides and running) is something I torture my kids with. If they mention a word or phrase that reminds me of a song, within seconds I have it playing for them. Most of these are older songs, and when they hear what I’m playing, they look at me bewildered, as if I’m wearing polka-dotted clothes dancing around playing an accordion. If they mention wanting candy, “I Want Candy” by Bow Wow Wow circa 1982 is soon streaming through my phone. When we talk about hip-hop and rap remixing tracks, I tell them, then have them listen to the originality of “Rapper’s Delight” by the Sugar Hill Gang. If the word “poison” is mentioned on the news, or if they read that something is poisonous, Bell Biv Devoe’s “Poison” is soon pumping through my phone and my kids see me awkwardly display my “Dad dance moves,” then blush when the lyrics turn to “Never trust a big butt and a smile” and my kids giggle. Now that I’ve seen that written, I’ll be rethinking the musical choices I play for them, come to think of it.

Hope this has helped, Frustrated Listener, and thanks again for writing in! If any readers want to comment on songs I should listen to, new or old, I promise to listen to them, and think it would be a fun string of comments on the site!


The Geek

Adam Darack is the IT administrator for the town of Edgartown. He writes regularly about the technological issues facing Island business owners. Got a question? Send it to with the subject line “Dear Geek.”