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Web browser and email client for 68k Mac?

LisaXL

Active member
Hi there,

I have a question regarding which web browser and email client I can use with the 68K Mac? The iCAB 2.9.9 can't really get on any websites. The Outlook Express doesn't allow you to enter account with "@" sign in it (for example "abc@gmail.com"). I need a mail client that can read mails from Gmail and Hotmail. Any help is appreciated.

Thanks.
 

LisaXL

Active member
As for the Email client, I have tried Green Mail, it doesn't work over SSL/TLS. I tried Eudora, Outlook Express 5.0.6, Mulberry... But they seemed to require a PowerPC Mac. Doesn't work either. It is frustrating.
 

CircuitBored

Well-known member
Hi there,

I have a question regarding which web browser and email client I can use with the 68K Mac? The iCAB 2.9.9 can't really get on any websites. The Outlook Express doesn't allow you to enter account with "@" sign in it (for example "abc@gmail.com"). I need a mail client that can read mails from Gmail and Hotmail. Any help is appreciated.

Thanks.
It is worth considering that the setup you are asking for is a security nightmare and there is no practical way to do it without opening yourself up to a lot of vulnerabilities. These are vintage machines with long-obsolete system software that has no idea what to do with the modern web. The WebOne proxy (included with @mactjaap's wonderful MacIPpi package for Raspberry Pi) does a pretty good job of getting vintage Macs online but it still has its pitfalls. You simply aren't going to get a pleasant experience browsing the web or even receiving emails on a 68K. Even the fastest Quadra is miserable at rendering eveslightly modern web content. Using SSH or Telnet to connect to a Linux host running Lynx or a similar text-based browser is actually one of the better ways to experience the web on classic Mac because it feels "retro".

Use a modern device with up-to-date security patches for web browsing and emails. Don't try to log in to anything modern from a 68K Mac. Seriously. Either use your Mac as a retro tunnel into a modern machine or do not take it online.

Enjoy your Mac but remember what it is. Think of it this way: you can own and drive a classic car to your heart's content but taking it on the highway is a disaster waiting to happen. Classic cars are missing all the underpinnings and vital technology that makes modern highway travel so safe. You can't see the differences beneath the surface but they are lethally important to be aware of. It's possible that you will be able to do it and get off scot-free but the risks simply aren't worth it. Take the longer, slower route. Keep your web presence secure. Most importantly: have fun with your beige!
 

LisaXL

Active member
It is worth considering that the setup you are asking for is a security nightmare and there is no practical way to do it without opening yourself up to a lot of vulnerabilities. These are vintage machines with long-obsolete system software that has no idea what to do with the modern web. The WebOne proxy (included with @mactjaap's wonderful MacIPpi package for Raspberry Pi) does a pretty good job of getting vintage Macs online but it still has its pitfalls. You simply aren't going to get a pleasant experience browsing the web or even receiving emails on a 68K. Even the fastest Quadra is miserable at rendering eveslightly modern web content. Using SSH or Telnet to connect to a Linux host running Lynx or a similar text-based browser is actually one of the better ways to experience the web on classic Mac because it feels "retro".

Use a modern device with up-to-date security patches for web browsing and emails. Don't try to log in to anything modern from a 68K Mac. Seriously. Either use your Mac as a retro tunnel into a modern machine or do not take it online.

Enjoy your Mac but remember what it is. Think of it this way: you can own and drive a classic car to your heart's content but taking it on the highway is a disaster waiting to happen. Classic cars are missing all the underpinnings and vital technology that makes modern highway travel so safe. You can't see the differences beneath the surface but they are lethally important to be aware of. It's possible that you will be able to do it and get off scot-free but the risks simply aren't worth it. Take the longer, slower route. Keep your web presence secure. Most importantly: have fun with your beige!

Well said and points taken. It seems there is no way to get access with web and email using the available programs for 68K Macs. I will inspect into Web One. Thanks for the lead. I just enjoy using the classic Mac OS so much that I hope to use it as my full time machine. I guess I will stick with playing Dark Castle and producing documents with Ready Set Go! That's enough to satisfy my nostagia.
 

AndiS

Well-known member
Everything written here is true, sadly.

I just want to specify it a bit more. iCab 2.9.9 is the most modern browser for 68k Macs. But as you discovered, it won't go to any modern websites. And even if it could display them (there are some sensible webdesigners left), it is not able to work with modern cryptography so https and with it most of the current web is out of the question.

Mail has the same problem. It should be possible to set up even very old e-mail clients with modern services like gmail. But then you hit the crypto wall again. Setting up a proxy between your client and the mailserver should be much more feasible than surfing the Web though.

There is one thing left that still works and that is IRC. I've even used ircle 1.5 to chat from a 8 Mhz Mac Classic and the experience is actually not bad. The only problem I encountered is that ircle uses the old MacRoman encoding and therefore does not display some special characters correctly. Otherwise it is great fun to use this old Mac to communicate with people whose wireless mouse controllers have more computational power than the Classic :)
 

beachycove

Well-known member
Just idly throwing this out here because, after reading through the above, I wonder if mail could work as a sort of retro-challenge-ish bodge:

1. Get yourself a fixed IP and a domain like classicmac.org or whatever/ go with a dyndns solution (but let’s keep it simple with a fixed IP and domain)
2. Get a Mac capable of running MacOS9.1 and AppleShare IP 6.3
3. Install 9.1 and AppleShare IP 6.3 on said machine
4. Start up the mail server in ASIP, give yourself an email account like whatever@classicmac.org, and set the port for your ASIP mail server in software and on your router to [something unusual]
5. Get a Google address
6. Set up a rule in said Gmail account that forwards all mail to whatever@classicmac.org:[unusual port number]
7. Install Claris emailer or another client of you choosing on your 68k Mac and set it as an email client of your ASIP server
8. Start up your 68k Mac and read your mail.

PS: I suppose any of the old mail servers could do this just as well, and not just ASIP….

Workie or no workie?
 

LisaXL

Active member
Thanks a lot for everyone's feedback. I am just wondering if there is any free public pop3 mail service that doesn't use SSL/TLS encryption? If there is such service, I would like to use it and forward my Gmail emails to it.
 

greystash

Member
I wrote a guide on this focusing on OS8/9 a while back and I'm still using email with Outlook Express occasionally. I've accepted there are security vulnerabilities with this setup but I enjoy using it and don't transmit anything of importance. There's a small annual cost involved with this method but since I'm a web developer it's mostly free for me so was the perfect solution to me - it may not suit everyone.
https://mac-classic.com/articles/setting-up-modern-email-for-early-mac-os-8-0-9-2-2/
 

Cory5412

Daring Pioneer of the Future
Staff member
As everybody says, there's unfortunately a couple different problems with accessing modern Internet services on vintage Macs. You either need to alter the service, use external help, or use/run services that are themselves, vintage friendly.

The first set of problems really comes down to Encryption generally not being "optional" at all these days. 68k Macs have a difficult time handling the flow of data in an "everything is encrypted" setting. Especially with modern encryption standards. They usually can do it but it is very slow.

The other set of problems comes in play when you start talking about offering services optimized for vintage computers. (This really generally applies to any computer from before around 2005 but due to certificates changing you can also see this stuff in software that hasn't gotten security updates in a few years.)

Old computers expect implicitly for everything to be trusted and for authentication to be optional and rare. Most old email clients don't have a way to ask for SMTP auth, and most old email servers don't require it and don't have a way to enable it.

In addition, most modern email servers do not trust servers that don't have certificates.

The third thing (I know I said two above) is that most modern email accounts are a veritable firehose compared to the IV drip of the way email worked in the '80s and '90s, or even the early '00s. My personal and work email accounts each get about 100 total messages per day. It would be more if I explicitly asked services and web sites for email notifications. My work email account takes about 7 gigs on disk and my newer personal one (the one I use with almost no automated services) is about ~5-8 or so total gigs.

It's outright unreasonable to attempt managing 5 gigs of email in one go on a Classic Mac OS computer. Almost any email program on any release of Classic Mac OS will just absolutely lose it with that much email. Heck, Macs didn't even support 4-gig volumes unless they have an '040 or better.

The fourth thing (yes, I know) is that most modern email has lots of imagery and styling that existing programs can't display and that would in general look bad on small displays. (Again: if the HTML engine in your email client were capable of rendering it.)

It is worth considering that the setup you are asking for is a security nightmare and there is no practical way to do it without opening yourself up to a lot of vulnerabilities.

Fun anecdote. I run a Mac OS 9 web and file server -- http://vtools.68kmla.org. I was originally planning on adding email to it.

As part of testing for that, I set up DNS and reverse DNS and got my ISP to open port 25, etc etc, turned the service on, and in under 24 hours had a bit over 4 gigs of backlogged mail traffic.

It turns out that basically every IP is always being scanned and AppleShare IP 6's email server software doesn't have any way to authenticate users, so it's just... open.

For better or worse, the Internet was radically different in 1998 to the wya it is now, both in severity and scale. The reason I noticed was because AppleShare IP's mail stack crashes (badly) if the one and only data file grows to more than 4 gigs. (Fortunately, at some point I'd set it to hold outgoing mail, so my IPs weren't, as far as I know, blacklisted.)

The other thing I had to do was ask other people I was testing with to allow the server in on their servers, which you can't guarantee public providers (Google/Microsoft/Apple/Yahoo et al) will be willing to do in perpetuity.

There's some work-arounds, you could set up a smarthost so that the email server looks modern to the rest of the world. And, you can put vintage access behind a VPN -- even an insecure VPN such as an unencrypted PPTP host will protect the mail access ports (in that case you're doing VPN to protect network ports, not to actually create privacy.)


Unfortunately, I haven't been able to find a PPTP client for any older than Mac OS 7.5.x on an '030 with 8 megs of RAM or better. You could use an older router to put an entire gaggle of vintage machines on a VPN, but I haven't tested or set that up and my home Internet isn't in a place where it would be reasonable to do that.

The next best option, I'd say, is to set up your email in a modern linux console client like alpine or mutt and use ssheven on a 68k Mac to connect to that machine.

I wonder if mail could work as a sort of retro-challenge-ish bodge:

I have done this and I can not emphatically enough say that I recommend against doing it. You'll pay 2x as much for business internet, your IP will get scoped instantly and you'll instantly receive literally more mail than ASIP can conceive of, and then your IP will be blacklisted.

This may be possible if you use a newer server OS but in general, I recommend against doing this unless you are an experienced email administrator who understands how things flow.

There is one thing left that still works and that is IRC.

We have an IRC channel for anyone who wants to hop in, vintage or modern: #68kMLA on irc.oshaberi.ne.jp.
 

Cory5412

Daring Pioneer of the Future
Staff member
I'm going to double down on this specific point:

Forwarding your modern email to a vintage computer is a bad idea. Aside form encryption and authentication - in my experience modern email accounts get hundreds of emails a day, totaling up to tens of megabytes. Most old email programs, even the very newest OS 9 era applications like Outlook Express 5 and Netscape 7, will handle that amount of data very poorly. You'll have to be very fast at either deleting things or splitting them out into different data files.

AppleShare 6, the server software beachycove and I mentioned, can only support 4 gigs of mail total for an entire server.

Add to that: vanishingly little of the email your modern email account receives will display correctly on any email client for Classic Mac OS, even Netscape 7 or Outlook Express 5 which are both from the late Mac OS 9 era.

The way to do this would be to set up a dedicated server like vtools.68kmla.org or whatever you wanted to use, and then find other people using vintage machines to communicate with.

If you use an appropriate SSL-stripping proxy you may be able to use a Classic Mac OS web browser to view the plain-HTML version of Gmail: https://support.google.com/mail/answer/15049?hl=en
 

WakelessFoil

Well-known member
Just idly throwing this out here because, after reading through the above, I wonder if mail could work as a sort of retro-challenge-ish bodge:

1. Get yourself a fixed IP and a domain like classicmac.org or whatever/ go with a dyndns solution (but let’s keep it simple with a fixed IP and domain)
2. Get a Mac capable of running MacOS9.1 and AppleShare IP 6.3
3. Install 9.1 and AppleShare IP 6.3 on said machine
4. Start up the mail server in ASIP, give yourself an email account like whatever@classicmac.org, and set the port for your ASIP mail server in software and on your router to [something unusual]
5. Get a Google address
6. Set up a rule in said Gmail account that forwards all mail to whatever@classicmac.org:[unusual port number]
7. Install Claris emailer or another client of you choosing on your 68k Mac and set it as an email client of your ASIP server
8. Start up your 68k Mac and read your mail.

PS: I suppose any of the old mail servers could do this just as well, and not just ASIP….

Workie or no workie?
It doesn’t have to be that complicated. I’ve received and sent gmail from my Macintosh Plus using Eudora 1.5 and a smtp/pop3 server on my local network. It’s not that difficult but no one has made good tutorials on this.
 

WakelessFoil

Well-known member
Thanks a lot for everyone's feedback. I am just wondering if there is any free public pop3 mail service that doesn't use SSL/TLS encryption? If there is such service, I would like to use it and forward my Gmail emails to it.
I used sTunnel as a pop server for receiving Mail and exim for sending. Both can easily be set up and run on a raspberry pi. Here’s my gmail in Eudora on my Mac plus. It runs pretty well actually. Even includes attachments and text formatting.
 

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