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Apple Mail no longer working with iCloud on G4 with Sorbet Leopard?

P

Power G-Man

macrumors newbie
Original poster
Sep 28, 2025
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Hello fellow G4 users!
On both of my 2 G4s, running Sorbet Leopard, Apple Mail stopped working late June 2025. Has been working flawless for years, running app-specific passwords.

The error message says that there is a SSL problem - unable to establish a secure connection.

Did Apple change anything on the server side?

What can I do? Any tips on how to make this work again?
Miss my fully functioning G4s and would like to restore the Mail function.

Thank you!
 
I am surprised it worked on 10.5.8 at all until recently.

There are three modern mail apps that should work on Leopard: sylpheed, claws-mail and nmail (the last one CLI, other two GUI). Perhaps try any of those. My ports have newer versions and fixed sylpheed, claws-mail and nmail will probably work in versions which MacPorts has.
 
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Assuming this is the same issue as on 10.6 – 10.9 (and possibly even newer, I don’t know), this is an SSL problem and it can be fixed with an IMAP/SMTP proxy. Aqua Proxy will do it, but it’s written in Go so I don’t have a way to make it work on PPC.
 
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Wowfunhappy said:
Assuming this is the same issue as on 10.6 – 10.9 (and possibly even newer, I don’t know), this is an SSL problem and it can be fixed with an IMAP proxy. Aqua Proxy will do it, but it’s written in Go so I don’t have a way to make it work on PPC.
Click to expand...

I am sure there are a lot of proxy software in C.
 
Thank you guys! Would prefer a fix that restores the function in Mail. In the mean time, I will explore Sylpheed and Claw Email. However, it seems that the system requirements are 10.6 listed for the packages.
Will see if I can manage to compile them on my old Mac.
Any other tips and tricks are welcome.
 
Power G-Man said:
Thank you guys! Would prefer a fix that restores the function in Mail. In the mean time, I will explore Sylpheed and Claw Email. However, it seems that the system requirements are 10.6 listed for the packages.
Will see if I can manage to compile them on my old Mac.
Any other tips and tricks are welcome.
Click to expand...
Make sure to use the binary repo from @Matias_ for PowerPC Leopard. He posted instructions in a couple other threads. Barracuda156 provides binary packages for Snow Leopard and 64 bit Leopard, Matias provides 10.5 for 32 bit, and I handle 10.4. Binaries will speed this along immensely.
Sylpheed is easier to get working, but hasn't been updated since 2018. This is a problem if your email provider only uses OAUTH2 authentication. Claws-Mail is much more future proof, since it supports OAUTH2 and is updated at least yearly (current is from February 2025)
 
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Power G-Man said:
I will explore Sylpheed and Claw Email. However, it seems that the system requirements are 10.6 listed for the packages.
Will see if I can manage to compile them on my old Mac.
Any other tips and tricks are welcome.
Click to expand...

I don’t think there is anything in either port to require 10.6. 10.4 will increasingly become problematic, since support is dropped, 10.5 in most cases should do fine.

Claws-mail uses GTK3, which has quite a number of dependencies, but you gonna need the same for a lot of other software (media downloaders, text editors, podcast managers, image viewers, FTP software, photo editing, you name it).
 
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Forest Expertise said:
Sylpheed is easier to get working, but hasn't been updated since 2018. This is a problem if your email provider only uses OAUTH2 authentication.
Click to expand...
Which providers are doing this?

Gmail at least can be used without OAUTH if you create an app password. I think this is the process for most of the big providers?
 
Wowfunhappy said:
Which providers are doing this?

Gmail at least can be used without OAUTH if you create an app password. I think this is the process for most of the big providers?
Click to expand...
I believe it is now the only way to use Outlook, but I would love to be wrong.
P.S. It may be my Outlook work email, rather than all Outlook emails.
 
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Forest Expertise said:
I believe it is now the only way to use Outlook, but I would love to be wrong.
P.S. It may be my Outlook work email, rather than all Outlook emails.
Click to expand...
For Outlook you have a bigger problem, which is it needs Microsoft Exchange rather than normal IMAP.
 
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