Hello I just registered to add to this thread.
As many of you, I started using Eudora Pro v2.1.2 on Win95 in 1996, when one day I found an installer file hidden in some obscure online directory (and found with Lycos search engine) and since I never looked back. I have been of course gradually been upgrading over time up to the last v7.1 in Pay mode, and I'm on a Server2003 workstation (and no, I am not even close to upgrading to any of the awful newer win options, besides as is this one does all I need, and feels crisp and agile, otherwise there is my secondary win7 laptop for other stuff that refuses to run on XP/2003). Anyway, I think Eudora is still the best email client out there, and even though over the years I gave a try to some "more modern" alternatives, I always quickly ended up going back to use my very comfortable Eudora. I did of course run into the TLS issue when providers started upgrading, and Hermes did solve the problem for me as well in regards to maintaining security up to date while handling my email accounts. But there is one single issue that I still have a problem with, and that is the other reason for this post.
As said before, after Hermes I was once again able to check and send email via TLSv1.2, I have my own server so all my email accounts are on that private server, no Gmail or any other public services. Not that I have anything against them, its just that I never needed them. Ok back to the main point, I also have an "Alternate Port SMTP Server" service at No-IP.com, which basically allows you to send emails without having to use your ISP provided SMTP, etc. I use this as an option because in these "modern" times sometimes when I send a (single) legitimate email to one of my customers, that might contain a link, PDF document attachment, or the subject is worded in a certain way, at times my regular SMTP server rejects the message and bounces it back as "High probability of spam" as it gets flagged without any real justification. Very frustrating to say the least, so in those cases its where the No-IP SMTP option comes in handy to solve the issue. I brought up the problem of the frequent false positive spam flagging to my server hosting company, but they said that there is not much they can do about it, as now a days most SMTP servers rely on a ever more strict set of rules on how to identify spam, and check other 3rd party databases about flagged addresses, IPs etc. Guess we have the spammers to thank for that escalation. I have been using this No-IP service for a couple of years now, and it can be really a big time saver, specially when it comes to be in quick touch with your customer when they are expecting you to be without having to pull out your hair.
So the one remaining issue I have with Eudora is that even tough at the beginning I was able to send emails securely through this No-IP SMTP service by setting the secure sockets mode to "Required StartTLS", about 6 months ago I started noticing that I was getting a very similar, if not the same error message as I saw on another site where the person was reporting not being able to get his Yahoo mail anymore onto Eudora: 'SSL Negotiation Failed - The connection with the server has been lost. Cause (1)', which he ultimately also solved by installing the Hermes patch. So I started trying the other secure sockets options, but none would work, except for the "Never" option, which means your emails are going out in the clear as text. Not the worst thing in the world unless you are with the CIA, but obviously not ideal either in these times where you never know who might be monitoring you. So I wonder if anyone has any ideas or has run into something similar, specially if you happen to have any services with No-IP as well. No-IP was of course the very opposite of helpful claiming they did not see any problems on their end with my account, even tough the server was clearly blocking my connection attempt, but we know why they do what now a days with these kind of TLS issues. I should also point out that I tried my SMTP service with Thunderbird installed on the win7 laptop, and of course it works just fine via TLS.
BTW I just wanted to mention that after doing the Hermes upgrade for all my multiple email accounts I am now having to set both inbound and outgoing secure sockets to "Required, Alternate Port", check the "Use submission port (587)" option, and in this way I get a Succeeded at TLSv1.2 negotiation result. The way it was before, set at Required StartTLS I was getting an error, and the negotiation error result indicated TLSv1 was being used. But as long as it works correctly I really don't mind what settings I need to use.
Thanks in advance for any recommendations and/or insights into my last remaining TLS problem with the NoIP SMTP service.