Classic email clients vs Gmail

The two main problems for the classic Mac OS geeks who still want to use their vintage Macs on a daily basis are browsing the Web and doing email. The Web browsing is the trickiest part, because it has changed a lot in these last ten years: standards, technologies, security, plug-in management and the like. Usually, those who want to try to browse around a bit will find that a combination of old browsers is mandatory, because sometimes iCab 2.99 renders a webpage less poorly than, say, Netscape Navigator 4.8; or Opera 5 handles some CSS more gracefully than Internet Explorer 5. There are always tradeoffs, especially in this territory, since the choices you have are limited to browser versions which are no longer supported. A notable exception is Classilla, currently under development and the only chance to have modern webpages display in a viewable, readable, usable manner for those who still use Mac OS 8.6 to 9.2. (This very blog renders correctly in the latest version of Classilla — 9.1 at the time of writing).

But this post is about email and email clients. Email is generally more manageable in a classic Mac OS environment, and gives much fewer headaches than Web browsing today. Unless you want to retrieve and manage your Gmail account(s), that is.

Towards the end of last week, I decided to do a casual experiment. I hunted, downloaded and installed as many decent classic Mac email clients as I could and tried to configure a Gmail account in all of them. This is the list of clients I have tried so far (in alphabetical order):

  • Claris Emailer 2.0v3
  • Classilla Mail module inside Classilla 9.1
  • Eudora 6.1.1
  • Eudora Light 3.1.3
  • Green Mail 1.0b13
  • MacSOUP 2.8.3
  • Mailsmith 1.1.8
  • Microsoft Outlook Express 5.02
  • Netscape Messenger (inside Netscape Communicator) 4.8
  • Netscape Mail module inside Netscape 6.2.3
  • Netscape Mail module inside Netscape 7.0.2
  • Nisus Email 1.6.1
  • PowerMail 4.2.1

Where to find them

All releases of Netscape browsers are at the Netscape Archive. You can download Classilla from its homepage. Eudora, Eudora Light, MacSOUP, Nisus Email and PowerMail 4.2.1 can be downloaded from the email section of The Mac Orchard (a great reference site for Mac software, and one of the oldest, being online since 1995). The website of the developer of Green Mail 1.0b13 has disappeared, but you can still download Green Mail from this page thanks to Microsoft Outlook Express 5.02 should be bundled in Mac OS 9, while Mailsmith 1.1.x will be harder to find. (My copy was graciously given to me by Mr Rich Siegel of Bare Bones Software, but I think it’s not cool to pester him. So if you have it laying around in some old hard drive or included in some old software CD-ROM, fine.)

The Gmail test

Since I already knew that some of these clients aren’t able to handle IMAP accounts, I only tried to set up a Gmail POP account. According to the Gmail Help page Configuring other mail clients, the general POP settings are as follows:

Incoming Mail (POP3) Server – requires SSL
Use SSL: Yes
Port: 995

Outgoing Mail (SMTP) Server – requires TLS or SSL
Server: (use authentication)
Use Authentication: Yes
Port for TLS/STARTTLS: 587
Port for SSL: 465

Account Name: your full email address (including or
Email Address: your email address ( or
Password: your Gmail password

The system I used for my tests is a Power Macintosh 9500/132, with 272MB RAM, a 4GB hard drive (with more than 2GB free), with Mac OS 9.1 installed and the base extensions set enabled.

For starters, the mere fact that Gmail requires SSL authentication for both POP and STMP connections leaves some of these clients out, because they simply do not support it. Claris Emailer and Eudora Light, for example.

Then there are other email clients which were sort of grey areas during setup. Green Mail, Mailsmith 1.1.8 and Nisus Email 1.6.1 let me specify that both POP and SMTP servers require authentication with a password, and Green Mail and Mailsmith even let me override the default POP and SMTP ports (usually 110 and 25 respectively) with the correct ports needed by Gmail, but the result for all these three clients is that when connecting they either hang or the connection times out.

You may find odd that I included MacSOUP in the bunch, because it’s usually considered one of the best newsreaders for Mac OS, but actually it can also handle email. For mysterious reasons, however, in my test MacSOUP just kept crashing and I couldn’t even try it. In the following days I’ll try to figure out what the problem is, and I will update this post in case I manage to test the software and have a definitive answer.

Now, the remaining clients (the various Mail modules of Netscape/Mozilla/Classilla, Eudora 6.1.1, Outlook Express 5.02 and PowerMail 4.2.1) all explicitly support SSL connections and theoretically they should all work with a POP Gmail account. In practice, though, I haven’t obtained clear-cut results. Netscape Messenger 4.8 (the email client inside the Netscape Communicator 4.8 bundle), for example, did let me specify SSL/TLS for outgoing messages (as you can see in the figure), but apparently it has problems with retrieving mail, since it hangs indefinitely upon checking.

Netscape Messenger 4.8 handles SSL/TLS connections, but I couldn't get it to work with my Gmail account.

I think I read somewhere that Netscape 4.x had problems in handling email accounts where the username must include the domain part (in this case the Too bad, anyway — Netscape Messenger 4.x has been my main email client for years and never gave me a problem. If you intend to use it for other email accounts that don’t require strict settings like Gmail’s, remember that version 4.x only supported one account. If you like (as I do) the Netscape Mail interface, I suggest you use a later version of Netscape (6.2.x, 7.x or Mozilla 1.2.1 or Classilla).

Back to my tests with Gmail, I had generally successful results with the Mail modules of Netscape 6.2.3, 7.0.2 and Classilla 9.1. Netscape 6.2.3 was incredibly slow and somewhat unstable, so I’m not recommending it. The faster of these three has been Netscape 7.0.2 for me, but your mileage may vary. These clients all support multiple accounts.

Eudora 6.1.1 at first didn’t work and unexpectedly quit. Always read the readme files, because you will find out that you need Macintosh OS System 9.0 or above, with CarbonLib 1.6. My Power Macintosh had version 1.1 of CarbonLib, so I had to find a newer version. Nevertheless, despite following the Gmail Help instructions for setting up Eudora on the Mac to the letter, I couldn’t send or receive emails. Eudora’s behaviour for email retrieval was strange, because it didn’t hang, timeout or give me any error, yet it didn’t download the test messages I had sent to that account. As for sending, all outgoing messages remained in a ‘queued for sending’ status, but they were never sent, not even by forcing Eudora with the Send Immediately command. This might be a problem with my system, though, so I would dare say that Eudora 6.x should work for you.

PowerMail 4.2.1 and Outlook Express 5.02 were the only two clients which worked flawlessly from the start. They both support everything a Gmail account needs, and I had no hassles in sending and receiving emails. As I commented on Twitter, I found rather ironic that a Microsoft product could be a winner, although it’s only fair to say that for a little while Microsoft did release proper software for the Mac, Word 5.1 being the first example coming to mind.

If I were to pick my favourite client to use with Gmail, I would choose PowerMail. Now, again, the irony is that PowerMail is the only commercial product of the bunch — in other words, it doesn’t come free. If you want to handle multiple Gmail accounts with a versatile and powerful email client for the classic Mac on a daily basis, I’m sure you won’t mind paying for PowerMail. The current version is 6, works on Mac OS X, and according to CTM Dev website a licence for 1-2 users costs $49 or 49 Euros (without SpamSieve) or $65 with SpamSieve. If you try to connect to CTM Dev through the older PowerMail 4.2.1 you get a ‘Service Unavailable’ error, so I guess you should contact the company and ask about pricing for the older classic Mac OS version of PowerMail. I will try to contact them and ask about this myself. Who knows, maybe they’re even willing to consider turning pre-Mac OS X versions of PowerMail freeware, given that now the majority of Mac users are on Mac OS X.

If, on the other hand, you just want some reliable, Gmail-ready client to use occasionally with your vintage Mac, at the moment the best option is Outlook Express 5.02, followed by Netscape Mail 7.0.2 and the mail module of Classilla 9.1. If you want to check and send email from your Gmail account using the Web interface, your best options are Classilla 9.1, iCab and Opera 5 (these last two work better if you connect to the mobile Gmail website).


So, here’s a summary:

Email client Result
Claris Emailer 2.0v3 Does not support Gmail
Classilla Mail in Classilla 9.1 Full Gmail Support. Works OK.
Eudora 6.1.1 Should work. Test on my Mac failed.
Eudora Light 3.1.3 Does not support Gmail
Green Mail 1.0b13 Did not work
MacSOUP 2.8.3 Unknown (Program crashed)
Mailsmith 1.1.8 Did not work
Microsoft Outlook Express 5.02 Full Gmail support. Works well.
Netscape Messenger (in Communicator) 4.8 Did not work
Netscape Mail in Netscape 6.2.3 Worked. Very slow.
Netscape Mail in Netscape 7.0.2 Full Gmail Support. Works OK.
Nisus Email 1.6.1 Did not work
PowerMail 4.2.1 Full Gmail support. Works well.


Keep in mind that I’m not discussing the intrinsic quality of these email clients, and that this casual testing was only to have a more precise idea of the current status of classic Mac OS email as regards to Gmail support. If you want to handle other accounts with standard settings that don’t require special POP/SMTP ports and secure authentication, you can basically pick any of these (and other) clients and you should be fine. At that point it’s a matter of personal preferences, habits, and needs. I love Claris Emailer, for example. During these tests I have rediscovered Green Mail (thanks to Grant) and I think I’ll stick with it for all my non-Gmail needs. Another favourite (and the sole email client on my PowerBook 5300) is Mailsmith 1.1.x. If you’re adventurous enough and are putting online your old 68k Mac, perhaps the best choice is going to be Eudora Light, since the other clients examined are either PPC-only or would turn out to be extremely memory-hungry anyway. PowerMail is an excellent all-around candidate and probably the most feature-rich (but remember the caveat about buying a licence).

I will definitely update this post as new information comes in, and I’ll write more extensively about email clients for the classic Mac OS in the future.

10 thoughts on “Classic email clients vs Gmail

  1. Thanks for this post Riccardo, detailed, well written and documented.

    I love classic macs and I love Gmail, I use this method to use both, a bit tricky but very effective:

    On OS X, using Stunnel, you can create an encrypted communication (SSL) as request by Gmail.
    All email clients without SSL support can receive and send using this connection, specifying the server for sending (SMTP) and receiving (POP) as “localhost” on a specific port. I use it with MacSoup on my MacBook Pro and it works fine.

    In this way, all the classic macs email clients, even 68K, which are on the same network of the mac OS X with Stunnel up and running, can send and receive using as server the network IP address of the mac with Stunnel.

    This is the Stunnel homepage:
    This is an interesting guide to setup 68K macs for use SSL for modern email:

    If you want to try this method and need help, just let me know.

  2. Thank you, Tommaso. When you talked about Stunnel on Twitter, I meant to take a closer look to it and add the information to my article, but I didn’t have the chance. Today I will, and perhaps I’ll write a follow-up in the next days. Again, thanks for the tip!


  3. I’ve been using Netscape Communicator 4.8 with Gmail Imap. It works fine. Outlook Express also works fine with Gmail’s Imap service.

    Another good POP client for System 7 through OS X is SweetMail. Doesn’t work with Gmail but works fine with many other services, in my case Lavabit.

  4. By the way, found your site a few months ago. I really enjoy your posts. Please continue your excellent work. I recently started collecting a few vintage Macs, an SE/30 and a Powerbook 1400c/166, and appreciate your perspective.

  5. Regarding user names that contain an ‘@’ symbol … try replacing the ‘@’ with either a ‘$’ or ‘%’ instead. This format should still get parsed correctly by the server, and it eliminates the issue of the user name appearing a a fully qualified email address.

  6. I’m actually having the exact same problems as you were with Eudora 6.1.1 (other than the CarbonLib one; I was already at 1.6). Please update if you manage to find out what the problem is!

  7. Okay, I’ve ended up using Outlook Express 5.0.6 and it actually has a pretty nice UI. Thought it would be useful for your other readers to know that it doesn’t work with Gmail if you check mark the ‘Always use secure password’ checkbox in Advanced Receiving Options; in other words, may sure you leave it unchecked:

  8. Looks like ‘img src’ tags don’t work here, so here’s the image I tried to link to:

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