Can you still use an old PDA today?

After looking at all the interesting facts about the various PDAs in this collection, you may be asking yourself: “Would it be possible to use an old PDA today?” And as always, the answer would be “Yes, but…”. This article will try to lay out the main obstacles to using an old PDA today, and how to avoid or at least work around most of them.

Uses of an old PDA

Before we go into the details of the obstacles, let’s first review in what ways an old PDA could be used today. Here is a non-exhaustive list:

As a holder and manager of personal information (PIM), such as your calendar, address book, phone book, to-do lists, and memos
As a means to make notes or longer documents on the go
As a calculator
As a way to read and respond to e-mail
As a way to listen to music and audiobooks
As a way to surf the web, mainly for information and news
As a way to use web apps, such as Google apps

This, of course, begs the question why you would want to do any of this, when you can do it very easily using a modern smartphone. And here you would have to provide the answer. Some people, like myself, would just answer “because I want to”, or “because I want to explore what is possible”, or even “because it is hard, and I like challenges”. Another reason cited by some users today is “I want to use it because it provides a distraction-free experience”.

So what are these challenges?

Let’s break down the uses of an old PDA into two categories:
A. Uses that do not require a connection
B. Uses that do require a connection

Uses that do not require a connection

This includes numbers 1-3 and 5 above, provided that you used the PDA exclusively to manage your PIM, make notes and listen to music or audiobooks. Of course you would have to find a way to get that music and audiobooks onto your PDA in the first place, but that could be solved by copying the files onto a suitable storage card, such as an SD card, that your PDA supports. For the PIM information – when you have a requirement to make use of that information on more than the PDA – for instance on your computer, then you would need a connection. More on that later. Let’s first investigate the use of storage cards:

Hurdles in using storage cards

Very old PDAs (from the 1980s through to mid 1990s) could only store information in RAM. Why? Well, flash memory had either not been invented yet, or was prohibitively expensive. Those who had a slot for memory expansion, usually had a proprietary slot for a proprietary RAM-card using a small coin-cell battery to retain the information. So not only would it be difficult to find such cards in this day and age, but they would be difficult to interface with a modern computer and in most cases fit too small amounts of data, in order to be usable as a storage medium for music or audio-books. Not that it matters though, because PDAs from this time-period were not powerful enough to even play audio.

Slightly newer PDAs started to include slots for CompactFlash cards once they were generally available. Although not so popular today, they can still be purchased both new and used. There are three main hurdles to overcome when using them today in a PDA context:

1. How to connect them to a modern computer (to get files onto them)

2. The storage size

3. The file system

No modern computer (PC, Mac, or otherwise) that I know of includes a CompactFlash slot today. However, there are several memory-card readers available that have a slot for CF-cards and that connects to a USB port of your computer. So this is a hurdle easy to overcome. The storage size hurdle is a bit trickier. The problem is that most older PDAs do not accept cards larger than 2 GB. New cards are considerably bigger. There are two possible solutions to this. Solution 1 is to find an old, used, card with a size of 2GB or less. The other solution is a bit more involved: Use a bigger card, and use disk partitioning software to create a partition (it has to be the first partition) that is 2GB or less. In my experience, this sometimes works, but not always, and there is no way of knowing beforehand if it will work or not. Once you have a suitable card at hand, you need to format it (or the partition) in a way that the old PDA – and the new PC – understands. This is usually FAT16. Modern versions of Windows do not make this easy. The normal format command or the option to format in Windows Explorer does not expose this option. There is other software available, however, to make this possible. Alternatively you can use an older PC with an older version of Windows to perform this. After reading the rest of this article, you may conclude that this is the easiest path anyway.

There was a brief period in time, before the use of CF Cards became the norm, when some PDAs used PCMCIA (later called “PC-Card”) as storage cards. These are hard to find today, but there are CF card to PCMCIA card adapters that can be used to transform a CF Card to the PCMCIA form factor. The same hurdles as described above apply to these, with the additional hurdle of finding a PCMCIA adapter that actually works with your computer and operating system.

Even newer PDAs, such as those released towards the end of the 1990s and in the 2000s will most likely have an SD card slot (unless its a Sony PDA – in which case it will feature a Memory Stick, Memory Stick Pro or Memory Stick Duo slot), making things slightly easier, but the same restrictions on size and file-system may apply. Remember – the SD cards have evolved over time too. First, there were SD card. Then there were SDHC card, and later SDXC cards. Best is to find a “pure” SD card. If you are the owner of a PDA from Sony, you will either have to find a suitable Memory Stick from the time period, or a micro-SD to Memory Stick adapter. Be sure to check the variant of Memory Stick that your PDA is using, first!

Uses that do require a connection

All other uses of a PDA require some kind of connection. The most usual scenario for the use of old PDAs is to connect it to a computer, usually a Windows powered PC, and synchronize information between the PDA and information residing in the PC. All PDA platforms had their own synchronization platform, and the things you would synchronize would differ. Before we go on to the software side of things, let’s look at the physical connection between the PC and the PDA:

Serial connection

Before USB was invented, a serial connection using something like RS-232C was the norm for connecting a PDA to a PC. On the PC side, the connector was usually a so called 9-pin D-Sub connector. The PC would have the female socket and the cable would have a male connector. D-Sub connectors were too big to fit in most PDAs, so manufacturers had to find something smaller that could carry the same signals. Usually this led to a plethora of proprietary connectors with no interoperability between PDAs from different manufacturers. Some used a special cable featuring its unique connector in one end and the D-Sub connector in the other, but more common was the use of docking stations. The docking station was the unit connecting to the PC, and when the PDA was put in the docking station, connection to the PC would be made.
Being used to the ease of use involved when using USB, it is perhaps hard to remember all the choices you had to make in the old days of RS-232C serial connections. Not only would you need to select the appropriate speed of the connection (ranging typically from 9600 bits/s to 115200 bits/s), but also whether parity should be used or not, and if there should be one or two stop bits per symbol. On the PC side of the connection, you also typically needed to tell the operating system which interrupt (IRQ) the connection should use.
Today, not many PCs contain a serial connector. To overcome this problem, you can use a serial-to-USB conversion cable. These usually work well. Remember to order one with the correct connector (female or male), fitting your PDAs sync-cable.

Parallel port connection

Although unusual, some PDAs like the Atari Portfolio, contained a parallel interface. Parallel interfaces were the common means of connecting a printer to a PC in those days, but the Portfolio used it to connect to a PC. Parallel interfaces are even more uncommon on modern day PCs, so a suitable adapter would have to be found. I have not yet investigated the availability of this.

USB connection

If you are lucky enough to have a PDA with a USB connection you will have no other problem connecting it to a PC than finding a cable with the correct connector. Back in the day the most common connector for a PDA would be a mini-USB connector, not to be confused with the micro-USB connector introduced later. The fact that most PDAs would run the old USB 1.1 standard, rather than USB2 or USB3 more common today is not a problem, as USB is one of the few standards where backward compatibility really works in practice.

IR connection

There was a time where users of PDAs, typically users of PalmOS powered devices, would exchange business cards with each other using the built-in infrared ports of their PDAs. Many PCs of that same era also featured infrared transceivers making it possible to transfer files between PCs and between PCs and PDAs. It should be noted that just because a device contains an infrared transceiver it could not always transfer a file to another device also containing one. This is because IR used different standards, and devices themselves would have to be compatible on the file level. The earliest devices with infrared ports often did not follow a common standard at all. The conclusion here is that although a very cool idea, in practice you would not have much use of IR today.

Other (esoteric) connection types

The Timex Datalink, being a wrist-watch with a normal form factor for wrist-watches, could not use a normal connector at all for transferring data between it and the PC. Instead Timex, in cooperation with Microsoft, invented a very clever way of transferring data between the watch and the PC. It used a special program on the PC that when invoked made the screen flicker in a particular way that the watch, with its built-in photodiode, could detect and translate to data. For this to work, the screen would have to be a CRT. A more modern LCD screen would not work at all. This of course poses a problem today where most CRTs has been dumped and are difficult to find, at least at a reasonable price. Also, if you do find a suitable CRT screen, how do you connect it to a modern PC? Most CRT screens would use a 15-pin D-Sub connector for its video connection, and these are only to be found on some server PCs today. Even if you had one of these, the program would not run on modern Windows. You could, of course, run a Virtual Machine that started an ancient version of Microsoft Windows, like Windows 98 SE, and that would be able to run the sync software. A better option would be to find an old PC that contains a proper VGA connector.

The software side of things

Wouldn’t it be great if all software ever written for Microsoft Windows would be able to run on a modern computer? Indeed it would. Unfortunately that is not the case. This means that if you really want to synchronize your old PDA with a program or programs that run on a PC, it would not automatically work, unless that PC is running a version of Microsoft Windows that supports that specific synchronization program and/or PIM-software. I say “Microsoft Windows” here, as it is the most common operating system supported by those synchronization programs. If you have a Mac or run Linux, you will face even more difficulties. So let’s say that your synchronization software is made for Windows 3.11 and Windows 95. What do you do? In many cases it will also run on Windows XP (32-bit edition). In most cases it will run on Windows 98, second edition (which is more stable and easier to work with than Windows 3.11 and Windows 95). There are basically two ways to deal with this:

Either you find an old-enough PC that is able to run that operating system natively, or
You create virtual machines inside your existing PC that can run those older operating systems.

Let me explain the path I have chosen. As my collection spans the entire period from the Psion Organizer in 1984 to the HP iPAQ 214 Enterprise in 2005, the synchronization software requires different versions of Windows to run. For the oldest software, I have found a laptop that runs Windows for Workgroups 3.11 natively. For most other software, I have a PC that is old enough to run Windows XP SP3 (32-bit edition) natively. For software that requires Windows 95 or 98, I have created a virtual machine (using an old version of VMWare) inside the XP machine that runs Windows 98, second edition.

File formats

Another, related problem to software is the problem of changing file formats. A document written in a recent version of Microsoft Word for instance is not backward compatible with an early version of that program. The same is true about the supposedly portable document format called “Portable Document Format” or PDF for short. Looking specifically at formats used for storing music, you would find that mp3 is generally speaking compatible across generations of devices, but earlier PDAs using less powerful CPUs may not be able to play them anyway if they have too high bit-rate.

How to transfer files between machines

You may think that as networked file transfer capabilities were introduced already with Windows for Workgroups, it would be easy to connect all machines to your LAN and start to transfer files. Wrong. For two reasons: 1) Exposing your LAN to very old machines is generally a bad idea due to security concerns. Old machines contain known security holes that cannot be patched and you do not want to risk one of these being exploited and to poison your LAN resources. 2) The SMB protocol used in earlier versions of Windows is insecure and have been turned off entirely in newer versions of Windows. So they cannot “talk” to each other, at least not using this protocol. Using a simple protocol like ftp would perhaps be an option, but instead of fighting with finding suitable software for that for the older machines, I came across something called copyparty, an excellent piece of software that exposes files to any machine in the network that has a web-browser. Basically any web-browser. As long as copyparty is not exposed to the internet, it should be safe. This is what I use in my homelab.

What if you want to read e-mail or surf the web?

Ah, now things get really complicated. Protocols used for connecting to Wi-Fi, an e-mail server or a web-server has evolved a lot during the last 20 years.
Let’s break it down:

Connecting to a Wi-Fi network

PDAs from the later part of the PDA era (from the 2000s), could contain a radio that was intended to connect to a Wi-fi network. Usually that radio would use the IEEE802.11b standard, or in some cases the 802.11g standard. The router you have in your home or at the office today would typically use a more modern standard such as the 802.11ac or 802.11ax standard. Most routers would be backward compatible to the older standards for connection, so this per se would not be a problem. The authentication to the Wi-fi network would be a problem, however. Early PDAs expected open network that required no authentication at all. Later PDAs relied on the WEP authentication scheme. As it was discovered that WEP security was in fact very easy to break, most manufacturers of routers have removed the possibility to authenticate via WEP. Even if it was available, would you want to leave your network open for anyone to get access to any resource in your network by exposing it via WEP? Of course you wouldn’t. So how do you deal with this situation? The most reasonable solution is to get an old router that enables authentication via WEP (or to use no authentication at all) and expose that to the old units. In order for it not to pose a threat to units on your LAN, you would either isolate it to only connect to the Internet but using a different subnet, or by using VLAN isolation, or to expose it to selected resources in your LAN (such as the excellent copyparty file server software) by using a routing firewall. I choose the latter approach in my home network.

What about dial-up Internet?

In most countries, dial-up internet service providers disappeared a long time ago. This makes software that assumes that the way you connect to the internet is through a dial-up ISP useless. Or does it? Well, as it turns out provided that you have some specific equipment, a bit of ingenuity and some spare time at hand, you can in fact be your own dial-up internet service provider, at least if you are going to connect one PDA or computer to the internet which is located in your own home. Since this is quite involved, I will write a separate article about it later, once I have done it myself.

Reading e-mail on your PDA

Old but connected PDAs supported SMTP for sending e-mail and POP3 for getting them from the e-mail server. Newer PDAs included support for the IMAP protocol that also supported the use of email folders and selectively getting what emails you wanted to download from the server. Although most email servers still support these protocols, in practice it is difficult or in some cases impossible to use it, because of other layers of security introduced in modern times. So if you really want to do this, you would probably have to set up your own email server, something that is less than trivial. If your PDA has a big enough display, and you can overcome the hurdles of the next chapter, you could possibly read e-mail using a web-based client.

Surfing the web

So your PDA has a web browser, such as Pocket Internet Explorer, or Opera Mobile or Netfront? Great! That would mean that you could surf the web using your PDA, right? No, not at all. At least not with a considerable amount of preparations to do first. Let me explain! In the early 2000s when PDAs were equipped with a web browser, the web was a happy place using simple web-pages served from a server to the client using the http-protocol. Web-pages consisted mostly of HTML-code and some images. Not so anymore. Today, because of security concerns, almost all web content is served through the secure https-protocol. Notice the “s” at the end. Web browsers from the early 2000s don’t support the https protocol at all, at least not those available in PDAs from that time. To be specific, old browsers could support SSL 2.0, SSL 3.0 and perhaps TLS 1.0. But modern web-pages use TLS 1.2 or TLS 1.3.

Then we have the problem of the content of those web-pages. Today most web-pages not only contain html-code and images, they contain vast amounts of CSS-styling code and Javascript code. Most of this is incomprehensible to the PDA browsers. It should be noted that the limited CPU power available in an old PDA also makes it impossible to display a modern web-page.

So what to do? Give up? Of course not! The first and easy solution that will always work without any effort is to use sites that specialize in displaying content for old browsers. One such site is http://theoldnet.com. Another is http://frogfind.com, a search engine specifically designed to find content that works well in older browsers.

But what if you really want to display a modern web-page on an old PDA? Then you would have to introduce a layer of translation between the internet and your old PDA. The PDA would send a request to see a modern web-page. The translator would intercept this message, get the content from the internet and translate it into a language that your old PDA understands and send it to your PDA. There are two types of such translators available. One works as a proxy server, that is you configure it in proxy server connection of your PDA. One such proxy server that works well is WebOne. The other type works as a home-page for your browser where you enter the url of the page you want to see, and it then displays it on its own page. This means that no proxy setting of your PDA is required. One example of this is Browserver. Both these are free and open source software that you can install on your own server. Combined with a firewall-router software and separate old Wi-Fi access point, you can create your own “retro-net”. This is what I have done in my homelab.

Here is a figure displaying my setup:

Retro PDA
   |
Retro Wi-Fi
   |
Firewall / Router
   |
WebOne / Browservice / local services
   |
Internet