This explains my history in classic Mac computing and the first sections of this arcticle depict how I got to the final state. Also, this article is a work in progress. Screenshots and other media to come.

Once upon a long time ago I was a young tech nerd. I'm still a tech nerd, just not so young. In the late 90's I was very much enamored by the Macintosh for a variety of reasons. Partly because of the stability of the operating system when compared to the Win 9x systems that were out there, and partly because of the pure sex appeal of the hardware and OS as compared to Wintel machines of the era.

As a young teenager, I couldn't afford to buy the brand new machines of the era, but used computers were obtainable. The first computer I purchased for myself was a Macintosh SE for a whole $30. The second computer I purchased for myself was a Macintosh Quadra 700 for $25 in the late 90's. Tech was moving fast and the PowerPC (PPC) architecture made the 68k machines obsolete almost overnight making them easily obtainable.

I joined the AppleFritter and 68kmla forums back then to learn more and share my own experiences as a Maintosh enthusiast and hardware hacker. I'm still technically a member of the 68kmla, but I haven't posted in years. You can find my ancient posts under the username foetoid. I had once upon a time dreamed of turning a PB 5xx into a wearable computer. From the late 90's to the mid 00's I collected ~60 68k and PPC machines. When I moved to the west coast, I had to let go of them unfortunately. I had all sorts of machines including a Quadra 950 and a WGS 95. I have grown to miss a number of these machines greatly and the cost to replace them these days simply isn't justifable.

Part of my collection included a PowerBook 520 and a PowerBook 520c. I loved the hardware design of these machines. Apart from the PowerBook G3 Pismo, there hasn't been another machine with more sex appeal in my opinion.

One of the easiest upgrades for the 520/c is upgrading to the 33Mhz 68LC040 from 540/c. It's a simple and inexpensive (relatively) parts swap from eBay. The costs of getting into the territory we're going to explore in this article starts reaching into the ridiculous, so unless you're a die hard or have money to burn, I would suggest that you simply enjoy the reading material.

What We're Doing

We're going to take a PowerBook 520c and make it do things that were never concieved of in 1994. Run more modern unsupported operating systems? Definitely. Remote control current operating systems? Absolutely. Connect to VPNs, access modern networks, and edit documents natively? Yup!

We're going to...

  1. Do a PPC CPU upgrade
  2. Run MacOS 8.6 where Mac OS 8.1 was the highest supported (Thought about going 9.x but RAM limitations are at thing)
  3. SSH into Linux boxes and do modern stuff
  4. Use VNC to connect and control modern machines
  5. Connect to VPNs
  6. Edit documents over the network using modern network protocols
  7. If I can find a revision C. PCMICA adapter, do this wirelessly
  8. If 7 is achievable, rebuild the battery pack and do this from the local diner


Because I can.

Why Not Use a 540c or a 550c?

First, the 550c is unobtainium. Secondly, if I find a 540c for the right price I might snag it to get the active matrix display. In this case, the 520c fit for a couple of reasons.

  1. I got it for an even $100
  2. It was in near pristine condition
  3. It screamed at me from a nostalgic place from my younger years

Getting Started

Getting started on my adventure I'm selecting a few components that are going to be crucial to my success while limiting my expense. By no means is this a list of things you must do in order to be successful, however, just what I chose to do.

Lab Environment

Getting started with this was quite the exercise in mental gymnastics. Afterall we're talking about using technology that existed in the days of Microsoft when Novell was cool. (When's the last time you touched and IPX/SPX network?)

I knew that I needed some bridging technologies in order to make this work. Going straight from Windows 10/11 or MOSS 10.x down to this level directly simply wasn't going to work. In this case I chose to use the following:


  • PowerBook 520c
    • CPU: 25Mhz 68LC040 -> 117 Mhz PPC 603e (Upgrade Card)
    • RAM: 40MB (8MB soldered to upgrade card, 32MB Upgrade)
    • HD: 160MB SCSI (Need a SCSI2SD adpater before this drive dies..)
    • NW: 10Mbps (AAUI adpater required)
    • OS: 7.1.1 (Starting) - 8.6 (Ending)
    • External Devices: Iomega 100MB Zip drive (required), SCSI CD-ROM drive (not explicitly required for this method, but could negate the need for the Zip drive.)
  • PowerBook G3 Pismo
    • CPU: 500Mhz PPC G3
    • RAM: 512MB
    • HD: 80GB IDE/ATA
    • NW: 10/100
    • OS: 9.2.2/10.3
  • Windows Server 200 Professional VM (Hosted on SuperMicro/TrueNAS iSCSI)
    • CPU: 1 vCPU @ 2.4Ghz
    • RAM: 1GB
    • HD: 100GB
    • NW: 1Gpbs
    • OS: Windows 2000 Server Professional
  • SuperMicro 1U Server
    • CPU: 2x AMD Opteron 6378 - 32 cores @ 2.4Ghz
    • RAM: 256 GB
    • HD: N/A
    • NW: 10Gbps
    • OS: VMware ESXi 6.7 U3
  • TrueNAS iSCSI Target
    • CPU: Intel i3-10100 3.6Ghz
    • RAM: 16 GB
    • HD: 22TB HD/4TB SSD
    • NW: 10Gbps
    • OS: TrueNAS 12.x
  • TrueNAS File Server
    • CPU Intel i3-10100 3.6Ghz
    • RAM: 32GB
    • HD: 40TB HD
    • NW: 10Gbps
    • OS: TrueNAS 12.x

Hardware Acknowledgements

For this particular exercise, there is no explicit need for the SuperMicro VMware or TrueNAS servers. Oracle Virtual Box or VMware Player will work sufficiently well to host the Windows 2000 server on your existing hardware. Just make sure that your network interface is configured as a passthrough interface so you're not isolated from the rest of your network. In my line of work, it's important for me to have this kind of lab equipment. (I know... It's a petty flex)

Hardware Required


  • Macintosh capable of running MOSS 9.x
  • PB 5xx series laptop
  • 32 MB RAM upgrade for PB 5xx
  • PPC upgrade for PB 5xx

Less Explicitly:

  • External Iomega SCSI Zip drive
  • External SCSI CD-ROM

Software Required


  • MOSS 8.6
  • ResEdit
  • WishIWere

Less Explicitly:

  • StuffIt Expander
  • Toast

Getting the PowerBook Ready

Aside from the realative unobtanium nature of PPC upgrade cards and 32MB RAM modules for the PB 500 series these days there were some early goals for this machine. The machine came with 7.1.1 installed on it. Network protocols were still very much up in the air at the point in history when the machine was released. AppleTalk was all that Apple supported out of the box. TCP/IP or IPX/SPX were additional add-ons. Even getting EtherTalk (AppleTalk over Ethernet) was something I had to conquor.

I was however able to get TCP/IP and EtherTalk working to get the machine connecting to my G3 Pismo running 9.2.2. That was good enough to get the machine updated to 7.5.3 in the early days of my ownership of the machine when it was still a 68LC040 with 4MB of RAM.

That is the one thing that Apple was so far ahead of the time with back in those days. SIMPLE network based OS installs and upgrades. This is going to be a theme in this article.

Getting to Mac OS 8.1

Before I got my hands on the PPC upgrade, but after I had the RAM upgrade in hand, my goal was to get the machine to a state that I remembered my old machines having from 15+ years ago. Luckilly for me I had anticipated that I might buy more classic Macs in the future and kept my AAUI tranciever and Zip drive along with all the necessary PowerBook cables when I moved. 8.1 was on the docket. With a 160 MB HD, there isn't much to work with from a storage perspective. Backups would be necessary.

Backing up data

While I could have backed up data to the G3 Pismo, for data integrity's sake, I decided that I would stand up a virtual machine running Windows 2000 Professional Server and enable File Services for Macintosh. This way I can take modern backups of my data for ease of recovery down the road.

IMPORTANT! It's important to note that for whatever reason you should not use Windows 2003 Server for this objective. While File Services for Macintosh were still available in 2003, I found that I could not connect my 520c running 7.5.3 to the 2003 server over AppleTalk. The 9.2.2 machine would work just fine. There are probably ways to work around this, however I did not explore this as I didn't see the value in it.

Installing Mac OS 8.1

After having a good backup, I obtained a Mac OS 8.1 ISO from a source where there is a full garden of Macintosh goodness. You do the math. I DO NOT advocate software piracy (no matter how old the software is). Somewhere in my boxes of software I have the original media (yes, I'm a data hoarder).

  1. I mounted the 8.1 ISO using Toast on my G3 Pismo and shared it using File Sharing.
  2. From the PB 520c I fired up Chooser and connected to the Pismo and mounted the 8.1 share
  3. I ran the MOSS 8.1 installer and bing bang boom, I upgraded 7.5.3 to 8.1 over the network.

Going to MOSS 8.6

Prior to install, you will need to fire up WishIWere and set it to PowerBook 5xx/PPC and restart.

Due to HD capacity limitations, I couldn't simply upgrade to MOSS 8.6 over the network, and it turns out my original MOSS 8.6 CD had becomed damaged over the years and wouldn't read in any of my Macs. Because of this, I again obtained a Mac OS 8.6 ISO from a souce where there is a full garden of Macintosh goodness.

My external SCSI CD-ROM only reads pressed CDs, so burning the ISO was out of the question. In order for me to install MOSS 8.6 I had to jump through some hoops.

I fired up my Zip drive and did a fresh network install of 8.1 to the Zip drive. I then selected the Zip drive as my Startup Disk and bounced the PowerBook. Once I was booted off of the Zip drive, I fired up Chooser and connected to my Pismo mounting the 8.6 share that was mounted on the Pismo. From there I formatted the 160 MB HD in the 520c and then performed a clean install of MOSS 8.6 on the 520c. Due to the limitations of the HD, I did a custom install, only selecting options that I needed to get the OS up and running.

Once the install was complete (and before rebooting), I fired up ResEdit and did the following:

  1. Scroll down and find the resource named "gusd" and open it.
  2. Open resource ID 1.
  3. Look for a line that says "007C 0024"
  4. Replace that line with "007E 0024"
  5. Save the changes to the System file, and quit ResEdit.



While I can boot into 8.6, Finder is currently crashing on boot. I need to do some more research as to why this is. It might be due to WishIWere running on the Zip disk and I might have to move all of that over to the PB HD. I don't know yet.

  • I moved the extension, control panel, and preferences over to the HD. No change.

Connecting to Modern Machines

You don't need to do the PPC/MOSS 8.6 to do this. This is also not specific to the PB 520c.

Software Required

  • MacSSH
  • VNC Client... Your Milage may vary on which VNC client works for you
  • VNC Server - Host Machine


If you want to connect to a Linux box via SSH, cryptography is going to be your enemy. I've found that Ubuntu 10.0.4 LTS (although out of support) will allow you to connect to it using MacSSH. Some specific settings need to be configured. (more details to come) From there, you can SSH to Ubuntu 20.04 boxes, and presumably other distros (CentOS/RHEL, etc)


You can install a VNC server on an Ubuntu 20.04 box and then connect via RDP to any Windows box you want, including Windows 11. Resolution and scaling will be an issue. Have also had problems with keyboard input. More to come.