I’m an updater. I check the App Store for iOS updates at least once a day, usually more. I always want the latest version with all of its new features and obscure bug fixes, because the newest is the best, right? And when the updates are free, why miss out on those new features?

Yet updates sometimes come with strings attached. Of course, some updates, especially on the desktop, are paid upgrades. If I’ve already paid for an app or been using it for free for a long time, I’ll keep using the old version until it breaks, or until I consider the new features worthy of a fee that’s usually less than a brunch date with my wife. Because I’m also cheap. And I’m more motivated to date my wife, even if I use that app every day.

But some updates come not with strings, but a burning fuse. Every time an iOS update installs, I anxiously check to make sure my Pebble Time smartwatch software still works. I’ve received the alert that PodBlaster, my favorite podcast listening app, is slow (32-bit) and will soon break, and the developer told me that he’s not developing it anymore. Other warnings are even more insidious. I use Magical Miles for mileage tracking, and it’s already unstable, but its available upgrade is a paid annual subscription service, a hard pill to swallow when I initially paid $5 for it but prefer free ad-based apps.

Desktop updates usually carry larger price tags, and much of the software of “the good old days” remains unmatched to this day. I got an overstock copy of Microsoft Word 5.1a in 1995, and the current version still lacks features it had when released in 1992, but 5 won’t run on my MacBook Pro, and even if it could, it’s not compatible with modern files. Microsoft Outlook Express 5 (1999) was the best email client ever made. If it came back with all of the features it had 20 years ago, I would run to it crying like a long lost lover. Oh, MSOE, how I miss you! GarageBand lost its podcasting capabilities. iMovie went from a professional-level video editor to a vacation clip organizer.

But time marches on, even if it takes steps back along the way. I miss my Palm Tungsten T3, but I love my iPhone, even if its calendar apps are just catching up now. I’ll keep upgrading, which will force me to eventually adopt new technology to remain compatible, and while I’ll miss certain features, I’ll gain the future.

What about you? What old features (hardware or software) have you lost that you miss?