You've got two computers you need to move files between. Software, saved games, documents… whatever the type of files, you've got ‘em on one computer. And you need to get them to another one.

Just one wrinkle – one of those computers was made in 2020 (let's say a laptop runnning Linux or Windows 10)… and the other was produced four decades earlier (let's say an old Apple II).

That modern, fancy laptop doesn't have a 5.25” floppy drive. Or a cassette tape reader.

And that Apple II doesn't have any USB-C ports. How the heck are you going to get files from one to another?

No doubt about it, you've got a connundrum.

Luckily there are a few solutions. Let's talk about two of them, each with their own strengths and weaknesses.

Note: None of this is actually hypothetical. These are solutions I use here, on a daily basis, to move files between several computers made in different decades – each with vastly different types of storage media and ports. These include a TRS-80 Model 100 laptop (from 1983), an HP 200LX (1994), Power Mac 6100 (also 1994), a Toshiba Libretto DOS laptop (1996), and my modern Linux desktop tower.

The first solution that springs to mind, in this sort of scenario, is to utilize storage adapters to allow for common storage media to be used between all of your machines… or at least as many as possible

For example: Your modern laptop or desktop (Linux, Windows, Mac, etc.) is likely capable of mounting and working with SD or Compact Flash cards. Possibly with an adapter of its own.

Luckily, there are many IDE->SD/CF adapaters on the market – like this one here which I used to replace the 2.5” IDE Hard Drive in my old Toshiba mid-90s laptop with a simple SD card. No drivers are necessary… at least not usually. There are similar flash storage adapters that can replace just about everything from floppy drives to scsi disks.

The result, most cases, is faster, quieter, and (often) beefier storage than what originally shipped on those multiple decade old machines. Going from a spinning disk (hard drive or floppy) to flash tends to bring about pretty significant advantages in those areas.

For the topic at hand – moving files between systems – the benefits are obvious. An SD card can be pulled out of one machine and mounted in another with relative ease. A quick way to move (potentially) incredibly large amounts of data between machines that don't typically share a common media type.

While I do tend to recommend people outfit any still-in-use, aging systems they have with exactly that sort of storage (the benefits are numerous and the price-tag cheaper than a fast food run)… this doesn't fully solve the problem.

  • There are machines out there that simply do not have easy to use conversion options to flash storage. Not many, but there are some… including when cassette tapes are used for storage. While solutions do exist, moving that data to modern systems can get tricky.

  • Needing to remove a primary storage mechanism (often requiring the opening of a case) is not always the most convenient. Who wants to break out the screwdrivers every time you need to transfer a few files around?

  • File system issues can arrise. While many systems can read FAT16 (making it a great option for moving many types of files), the compatibility will never be 100%.

Luckily, there is a different kind of solution to moving files between such fundamentally different types of computers…

Modem emulators.

A device that plugs into the modem port (often an RS 232) of (nearly) any computer and emulates an analogue dial-up modem… but provides access to Internet services. Thus providing a way to Upload and Download files from just about any type of computer. If it can use a modem – even a slow one – this option becomes a very viable solution.

Getting started with emulating a modem is surprisingly approachable. And there are multiple options, each with their strengths and weaknesses.

The first option is the “do it yourself” approach. You'll need:

  • a computer with a USB port (Windows or Linux will both work here)

  • a “USB to RS-232” adapter cable (you can pick those up for less than $15 from Amazon or multiple other stores)

Plug the Serial / RS-232 end into your aging, “retro” computer. Plug the USB end into your computer (a Raspberry Pi will work great). Then run an open source program called “tcpser” – a simple terminal program which emulates a dial-up modem (with lots of options) and allows the older computer to connect to internet services (like Telnet BBS's), utlize the shell of the Linux machine, and even Upload and Download files.

This solution is powerful and extremely flexible.

It is also… a bit clunky. Needing a entire computer to emulate a modem isn't exactly a stream-lined, super mobile experience. This is made a bit better by using a Raspberry Pi (or Pi Zero), but still not ideal for all situations.

Which brings us to the other option: Standalone Modem emulators.

There are, relatively inexpensive, compact devices (smaller than a deck of cards) that incorporate that core functionality into a more portable package.

A popular one being the WiModem232.


What's super cool about these sorts of devices, is they support just about any baud rate (300 on up) – so they tend to work with just about any computer (even ones made in the 1970s and 1980s)… and this one provides ways to configure a WiFi connection straight from the terminal program on that mult-decade old system.

Ok. Now, with either of those options, you've got the ability to get your 40 year old computer connected to the Internet (at least with the ability to use Telnet). Now what?

Now, I recommend setting up a Telnet BBS.



Because, quite simply, a Telnet accessible BBS (even one with no functionality turned on except the ability to upload and download files) gives you a central point to move files around. Think of this like your Nextcloud or Dropbox account. Except this is accessible from any computer with a terminal program… which is just about every computer since the Jimmy Carter administration.

I've written up a tutorial on getting a BBS set up under Linux to get some of you started down that road.


What if you didn't want to go down that road? What if you don't feel like setting up and running a Telnet BBS just to move a lot of files around?

Check out the GuruModem.


The GuruModem is very similar to other standalone Modem emulators (like the WiModem232 we just talked about)… but it adds in something that completely changes the game…

A micro-SD card slot. With a built-in shell. And the ability to transfer files (using XModem and ZModem) from the terminal program on almost any computer.

Guru Shell

What I do:

  • Plug the GuruModem into my DOS Laptop. In the terminal program type “AT+SHELL”… and, boom, I'm dropped into a shell (which can use both UNIX and DOS style commands).

  • Upload a file to the SD card from my local computer.

  • Pop out the SD card from the GuruModem… and plug it into my modern Linux laptop.

Laptop and Guru

This little miracle gadget provides the easiest mechanisms for moving files around on older machines… that I've ever seen. Get old computers “On-Line.” With access to an SD card. This is, straight up, a game changing set of functionality for anyone who wants (or needs) to use aging hardware and operating systems.

There you have it. My recommended ways for getting computers – from decades apart – talking to each other and sharing files. I use all of these, in combination, to provide me the best of all possible options. GuruModem for getting older machines On-Line and moving around documents I'm working on… in addition to Flash to IDE type adapters to make moving much larger sized files (when needed).

Though, if I had to pick just one solution, it would certainly be the GuruModem. Portable, easy to use, highly flexible. Can't recommend it enough.


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