topic Re: SSL Negotiation Failed: The connection with the server has been lost in Email

SSL Negotiation Failed: The connection with the server has been lost

Anneyc — Tue, 09 Sep 2025 12:17:52 GMT

Hi,

Since last night both myself and husbands have stoppped receiving emails on our separate computers, and this pop up appears when trying to check for new email: 'SSL Negotiation Failed: The connection with the server has been lost'.

We are receiving the emails on our Apple devices fine, so I'm guessing there is something in our SSL settings on our PC's email client which is no longer allowing emails to be received.(We use Eudora- I know, we're old)

Digging into the 'checking mail' settings, I have 'If available, STARTTLS' selected, and 'last SSL info' shows version TLSv1, Negotiation status: 'failed'. The server ip address is set at port 110 but I can't see a way to change it if I need to. Can any one shed any light? Tia

Re: SSL Negotiation Failed: The connection with the server has been lost

Anneyc — Tue, 09 Sep 2025 12:20:49 GMT

As an experiment I have just set the 'Secure Scockets when receiving' drop down list to 'Never' and the emails have now come through. Not sure it's safe to leave it like that though?

Re: SSL Negotiation Failed: The connection with the server has been lost

MisterW — Tue, 09 Sep 2025 13:39:27 GMT

@Anneyc

he server ip address is set at port 110

Port 110 is for an unencrypted POP3 connection. Port 995 is the POP3 port for an encrypted connection, select the SSL option rather than STARTTLS.

Re: SSL Negotiation Failed: The connection with the server has been lost

Anneyc — Tue, 09 Sep 2025 14:13:51 GMT

Thanks @MisterW, the options I have are: 'Never', 'if available STARTTLS', (which is what I had selected), 'Required alternate port' and 'required STARTTLS'. I just tried 'Required alternate port' and the info for this now shows port 995, but is still failing...

Re: SSL Negotiation Failed: The connection with the server has been lost

MisterW — Tue, 09 Sep 2025 14:25:39 GMT

@Anneyc what email client are you using ?

Re: SSL Negotiation Failed: The connection with the server has been lost

Anneyc — Tue, 09 Sep 2025 14:28:26 GMT

Eudora. Am thinking it might be a certificate issue- did a quick search and came up with 'probably Eudora not accepting the secure certificate from the server because that certificate is too recent'.. I know there were certificate issues recently with ios but not sure if it's connected?

Re: SSL Negotiation Failed: The connection with the server has been lost

MisterW — Tue, 09 Sep 2025 14:56:31 GMT

@Anneyc

Eudora! that's a blast from the past, we used to use it in the office. AFAIK its long been end-of-life.

A google search fro 'eudora pop3 ssl' returns this from the AI bot , so you may well be correct about the certificate issue.

To set up Eudora for POP3 SSL, you must use the secure port, typically 995, and enable SSL/TLS in the account settings under the "Checking Mail" category. A common issue is Eudora's outdated trust store, which causes it to reject new SSL certificates; this can often be resolved by manually importing the server's certificate into Edora's certificate manager or by installing third-party patches like HERMES. Eudora is no longer supported, so it's crucial to stay updated with necessary patches to maintain security and functionality.

Steps to Configure Eudora for POP3 SSL

Access Eudora Options: Go to Tools > Options in the Eudora application.

Navigate to Checking Mail: In the left-hand Category list, select Checking Mail.
Set the Mail Server: Change the Mail Server to the secure server name provided by your email provider (e.g., secure.emailsrvr.com).
Select the Secure Sockets Option: In the "Secure Sockets when Receiving" drop-down menu, choose STARTTLS or Required, Alternate Port to enable a secure connection.
Use the Secure Port: The default POP3 port for secure connections is 995.
Handle Certificate Issues: If you encounter "Server SSL Certificate Rejected" errors, click the "Last SSL Info" button and then "Certificate Manager" to import the certificate, or install patches like the HERMES patch to resolve issues with updated certificates.
Save Settings: Click OK to save your new settings.

Why You Might Encounter Problems

Outdated Certificate Store:

Eudora's built-in list of trusted certificates is outdated, leading to errors when connecting to servers using newer certificates.
Lack of Support:

Eudora is an unsupported and end-of-life product, meaning it doesn't receive updates for security vulnerabilities or new features.

Recommendations

Update the Certificate:

Manually add the server's certificate to Eudora's certificate manager to trust it.

Install Patches:

Install third-party patches, like the HERMES patch, to address certificate failures.
Switch Clients:

Given Eudora's end-of-life status, it is strongly recommended to migrate to a modern email client for better support and se

Re: SSL Negotiation Failed: The connection with the server has been lost

Anneyc — Tue, 09 Sep 2025 15:14:36 GMT

Thankyou MisterW.

I am keen to keep using Eudora if I can. The only option under the 'Secure sockets' list that works is the 'Never' option. There is a facility to import certificates in the 'Last SSL Info' menu, but I wouldn't know where to begin with that! Are you able to advise? Is the patch from HERMES a more permanent solution? (When I click on the link in your message I am directed to the Courier, and a search of 'Hermes patches' takes me to a list of suppliers of iron-on patches :-)- help!)

Re: SSL Negotiation Failed: The connection with the server has been lost

jab1 — Tue, 09 Sep 2025 15:21:03 GMT

I suspect that AI generated response is a little 'off' - I get Hermes Logistics, the clothes retailer and various other sites suggested by Mr. Google, but no reference to Eudora at all.

Re: SSL Negotiation Failed: The connection with the server has been lost

MisterW — Tue, 09 Sep 2025 15:39:13 GMT

@Anneyc I'm sorry but we stopped using Eudora years ago, and we only used it in a local network so no need for SSL.

As @jab1 says , the AI bot could well be a little 'off'. ISTR that when we ditched Eudora we moved to Thunderbird, there was an option to import from Eudora back then, whather that still exists I've no idea. The fact that you're using POP3 makes changing clients more difficult. POP3 stores mail locally, so when changing clients you need to be able to import mail from the old client to the new.

Re: SSL Negotiation Failed: The connection with the server has been lost

outcast — Tue, 09 Sep 2025 15:56:42 GMT

Here are the Hermes files - https://sourceforge.net/projects/hermesmail/files/

The underlying problem with Eurora is that it is using TLS v1, and requires patching to get to a minimum of TLS v1.2.

I'm wondering whether this is a migration consequence of moving Plusnet email to Greenby, where Plusnet which hasn't been maintained for years probably still functions with TLS v1, whereas almost all email providers now enforce a minimum of TLS v1.2.

Therefore is likely to cause issues on Greenby for customer's who have old PC's that haven't been updated to TLS v1.2.

Re: SSL Negotiation Failed: The connection with the server has been lost

jab1 — Tue, 09 Sep 2025 15:50:43 GMT

Ah, Google obviously doesn't like freeware/shareware sources.

Re: SSL Negotiation Failed: The connection with the server has been lost

outcast — Tue, 09 Sep 2025 16:03:31 GMT

No, you just searched for the wrong thing, as the link was the first result Google listed.

Re: SSL Negotiation Failed: The connection with the server has been lost

outcast — Tue, 09 Sep 2025 16:17:29 GMT

FWIW, I'd also recommend upgrading to Thunderbird and attempting to import the Eudora settings.

Trying to maintain an email client that ended support in 2006, and started breaking TLS and certificates around 2015, isn't sustainable.

@MisterW wrote:

... when we ditched Eudora we moved to Thunderbird, there was an option to import from Eudora back then, whether that still exists I've no idea.

Not on current Thunderbird, but you can by downloading an old Thunderbird first, in order to do the Eudora import.

This looks like a good place to start - https://support.mozilla.org/en-US/questions/1228297

Re: SSL Negotiation Failed: The connection with the server has been lost

jab1 — Tue, 09 Sep 2025 16:18:42 GMT

@outcast Following that link in the AI generated response - which is a link to Googles search engine takes you here: https://www.google.com/search?client=firefox-b-d&sca_esv=e7bf22627bcd1c5c&cs=0&q=HERMES&sa=X&ved=2ahUKEwiQjKTu9suPAxWJQkEAHRuNMV4QxccNegQIBRAB&mstk=AUtExfDRLn3JdUuuTF1IRXg2uVI7ZLAg8yuqq_3YWgQhAKSQY3o-4t0UA1XK8dqSMfin0-sihGZDDJvs3k3n1uUb4q9AAUyFz4zIOCwZ_Y_BWIoCzrvi9BeSpXMvBS-Hrfy5weSPq0TRHxpo-L18i32cniM6W7W9ejBUmjZSZl_qiHoGJF9ZTEnqePVjkUS2VcBbaS5s&csui=3

Admittedly, there are a number of pages following, but if you are searching for the information requested by @MisterW , that, and not clothing/logistics, should be reflected in the primary results page. IMHO, of course.

Re: SSL Negotiation Failed: The connection with the server has been lost

outcast — Tue, 09 Sep 2025 16:28:54 GMT

@jab1 - I'm guessing that you can't see my screenshot in Reply #13 ?

When is @James_B going to fix this useless image censorship filter, that is stopping this forum from working ?

Re: SSL Negotiation Failed: The connection with the server has been lost

MisterW — Tue, 09 Sep 2025 16:31:14 GMT

@outcast He can now

Re: SSL Negotiation Failed: The connection with the server has been lost

jab1 — Tue, 09 Sep 2025 16:37:17 GMT

@outcast nope, obviously I ~~can't,~~ couldn't, otherwise I wouldn't have posted the result from the link in @MisterW 's post.

As to when the image editing/approval issue is going to get fixed, by Plusnet - how long is a piece of string?

Re: SSL Negotiation Failed: The connection with the server has been lost

outcast — Tue, 09 Sep 2025 16:49:21 GMT

This is quite an interesting reading regarding Eudora certificates -

https://blog.timeoff.org/rick/2015/09/09/revisiting-eudora-ssl-certificate-failures/

IMO, although interesting for 2015, now in 2025 an alternative email program needs to be found.

I'm going to stop looking at this now, as trying to find fixes for Eudora is not a good use of my time.

Re: SSL Negotiation Failed: The connection with the server has been lost

Anneyc — Tue, 09 Sep 2025 20:07:08 GMT

Thankyou to everyone for your input. I do have Thunderbird too but have been using Eudora with no issues for the last 20 odd years so if there's a way to continue then I'll keep going!

I found some more recent info on AskWoody which has links to the Hermes files, though apparently there is also an updated version:

'The only fix is to use Pete Maclean’s QCSSL.dll update package from his HERMES Aurora work:

https://www.maclean.com/downloads/QCSSL_Update.zip

Pete Maclean is the Hermes coder.'