ChatGPT Helps me Open a 27+ Year Old Newton Backup File!

Yes, as a lifelong nerd I of course had an Apple Newton back in 1994 when I was a senior in high school. Check out this photo I took of my Powerbook and Newton together likely in 1994 or 1995:

The Newton had a companion app for backing up and synchronizing called the “Newton Connection Kit” or NCK. Apple being Apple this was an optional software package that did not come bundled with the device.

One of the neat things about the Newton Connection Kit software was that it allowed data from most of the core Newton applications (calendar, notes, contacts, etc) to be edited on the host Mac or PC. It stored everything in a single file that I have preserved all of these years.

Every so often I boot up Basilisk II on my modern Mac and tool around with some of the old Mac apps I enjoyed as a kid. (This process, by the way, is a heck of a lot easier now with the awesome Infinite Mac website that’ll load things up in a web browser with zero configuration).

During one of these tinkering sessions I stumbled across the file and remembered how the NCK used to work. So I headed over to the Macintosh Repository and found a working copy of NCK, installed it, and then discovered that my old backup file wouldn’t open.

This was due to the file losing its Mac file type and creator information. Unlike the PC that uses a file extension (like .DOC for a Word document) the classic Macs stored the originating application inside the file itself. Oftentimes transferring the file from a Mac to a PC like I must have done years ago stripped the Newton backup file of this information. Because of this the NCK software couldn’t see or open the backup.

I searched extensively over the last couple of weeks looking for the four letter code needed to get this file open to no avail. So I asked ChatGPT 4:

Its answer of “pkgb” was unfortunately not the right one. It was close though – pkgb is the file type for Newton’s equivalent of apps that the NCK software would also install back in the day. Many times people would email these apps to each other and found the NCK software didn’t know what to do with them.

So then I asked ChatGPT a followup question: “On an old Mac how might I look up what file type an application is looking for?”

Its step-by-step response led me to the right answer.

After following ChatGPT’s instructions using the Mac’s old “Resedit” utility I was able to quickly drill down into the 1994 application and get my answer. The correct file type for NCK backup files is “DCKb.”

I added that file type to my backup file, double clicked and BOOM! Suddenly everything that was on my Newton that day in 1995 was once again available to me.

To be honest there wasn’t much that was all that interesting. But there were some nostalgic calendar entries like the date of my high school graduation:

The rest of it had a bunch of random notes from high school and college classes but also a few fun things like this drawing a friend of mine made on the Newton on October 28, 1994:

What’s amazing about ChatGPT is its ability to sift through all the garbage you might get in a search result and guide you to the right place. It doesn’t always get things right as we saw here, but generally it will point you in the right direction.

If you’re curious about the Newton I made a video about this classic PDA platform a few years back when the iPad gained handwriting recognition functionality. It’s amazing how far ahead of its time it was.

Newton Makes a Cameo in For All Mankind

I love the Apple TV+ show For All Mankind. It’s an alternative history sci-fi drama where the Soviets landed on the moon ahead of the United States. There’s something for everyone with this show which is helmed by Ronald Moore who previously worked on Deep Space Nine and Battlestar Galactica.

Season 3, which just launched this week, takes place during an alternative 90’s where the Soviets and Americans are racing to get to Mars. And being an Apple show they are of course using Newtons as their personal digital assistants!

Unfortunately the Newton’s screen never looked this good. The best they could do was a green “indiglo” that was popular on some watches back in the day.

Perhaps all of the space age tech that developed out of the alternative space race in For All Mankind made for better displays!

Read and watch more about Newton in this recent blog post.