Discussion:
SSL certificate issue - cannot get into the certificate manager
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zazie
2015-02-16 15:13:12 UTC
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I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
zazie
2015-02-16 15:24:05 UTC
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Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
I forgot to add:
* I have added the certificate under properties, "incoming mail",certificate manager - but this did not resolve the problem
* and I still cannot get into the certificate manager under the generic properties
Ajo Wissink
2015-02-16 23:20:33 UTC
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Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
Just try to send a message. That will get you into the manager.
zazie
2015-02-17 08:42:46 UTC
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Post by Ajo Wissink
Just try to send a message. That will get you into the manager.
but no (I tried that of course) - it does not....

Sending an mail gets the "SSL negotiation failed [...] cause 200" error
and the SSL screen showing the certificate pops up ("The server's SSL certificate was rejected [...] unknown error") and no matter whether I try yes or no, I do not get into the manager under the generic properties tab. When I go to properties of the personality under the generic properties tab, it gives me the message that I have not used this personality.

So - somebody knows what to do ? Really hope so - if this forum does not, then who does.... Zazie
zazie
2015-02-17 11:00:14 UTC
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Update - after contacting the helpdesk of XS4ALL (my very reliable provider in the Netherlands):
* there are more Eudora users with the same issue
* XS4ALL uses a new type of certificate which uses a new hashing method

This may result in the fact that, despite answering "yes I trust this certificate" when the first error message pops up, the certificate is not accepted by Eudora - therefore no mail is sent and therefore the certificate manager is not accessible.
I have asked XS4ALL to send me more information about the new certificate so that I can post it here and hope that someone knows how to tell Eudora to work with the new type of certificate.
In the meantime, I have switched off using secure sockets and hope for the best...
Ajo Wissink
2015-02-17 11:27:45 UTC
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Post by zazie
* there are more Eudora users with the same issue
* XS4ALL uses a new type of certificate which uses a new hashing method
This may result in the fact that, despite answering "yes I trust this certificate" when the first error message pops up, the certificate is not accepted by Eudora - therefore no mail is sent and therefore the certificate manager is not accessible.
I have asked XS4ALL to send me more information about the new certificate so that I can post it here and hope that someone knows how to tell Eudora to work with the new type of certificate.
In the meantime, I have switched off using secure sockets and hope for the best...
Don't bother with the error messages and answering yes. That most
often does not work.

Here is again what Katrina in the Eudora mailing list says:

**********************************************

Open the properties for the personality in question and go to the
"incoming mail" tab.


Click on the "last SSL info" button at the bottom.


Click on the "certificate information manager" button


You'll get a window that lists certificates. The certificate(s) for
the current connection are at the top. If there is a plus sign next to
the one that is visible, click on it. Continue clicking on the + signs
until you can see the entire certificate chain.


Certificates that are trusted have happy face icons. Certificates that
are "bad" have skull icons. Select the one with the skull icon then
click the "add to trusted" button.


Click on "done" then close the windows to get out of the personality's
settings.


Do a mail check.


Repeat as many times as necessary until there are no more untrusted
certificates

***********************************************

You may also have to do this with sending mail.
zazie
2015-02-17 17:47:04 UTC
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I am sorry - I must have been very unclear in my previous posts !! Ajo's answers point me to all the directions I have already investigated...
Post by Ajo Wissink
Don't bother with the error messages and answering yes. That most
often does not work.
NO, indeed, it only works for that particular message - but apparently you need to do that in order to get access to the certificate manager.
Post by Ajo Wissink
Here is again what Katrina in the Eudora mailing list says: [...]
YES, and indeed I have done that (yearly, in the past) but NOW it does not work since I cannot get access to the certificate manager.
Post by Ajo Wissink
You may also have to do this with sending mail.
YES indeed and that is where the problem starts - usually, normally, always since now that did work but now I cannot get into the certificate manager under "generic properties" (which is where the sending information goes): it gives me an error message (see previous post).

Please let me know how I can be clearer about what I have tried and what did not work ? So that we can proceed to the next step? Thank you !!!!
3***@gmail.com
2015-04-17 22:51:31 UTC
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Post by zazie
I am sorry - I must have been very unclear in my previous posts !! Ajo's answers point me to all the directions I have already investigated...
Post by Ajo Wissink
Don't bother with the error messages and answering yes. That most
often does not work.
NO, indeed, it only works for that particular message - but apparently you need to do that in order to get access to the certificate manager.
Post by Ajo Wissink
Here is again what Katrina in the Eudora mailing list says: [...]
YES, and indeed I have done that (yearly, in the past) but NOW it does not work since I cannot get access to the certificate manager.
Post by Ajo Wissink
You may also have to do this with sending mail.
YES indeed and that is where the problem starts - usually, normally, always since now that did work but now I cannot get into the certificate manager under "generic properties" (which is where the sending information goes): it gives me an error message (see previous post).
Please let me know how I can be clearer about what I have tried and what did not work ? So that we can proceed to the next step? Thank you !!!!
I am also experiencing the exact same problem as you in that I started receiving the SSL Certificate Error for each of my e-mail accounts (personalities) and the message for each account that the certificate was bad and that the host name and certificate names do not match.

I also can not get past the "Last SSL" box as like you I receive the "you have never checked mail using an SSL connection" message and like you can go no further.

Although with a different ISP provider (Netregistry) my problem started when they upgraded a few days ago, did you ever get your problem solved and if so what was the fix to let you get past the "Last SSL" problem

Any advice will be greatly appreciated.

David
Bob Kingsley
2015-08-10 03:06:34 UTC
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Many of us are having the same problem. Click on "Last SSL Info" and get

"You have never checked (sent) email using an SSL connection ---"

I have tried both sending and checking but can not get to the next step. Suggestions please!
Ajo Wissink
2015-08-10 08:51:09 UTC
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On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
BobbyK
2015-08-28 00:04:47 UTC
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On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.

BK
Ajo Wissink
2015-08-28 01:25:28 UTC
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Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
If you have tried to send a message, or have tried to check mail, and
you still get that error message then there must be something else
wrong. I suggest that you pose your question in the Eudora mailing
list:

http://www.listmoms.net/eudora-win/

Ajo
BobbyK
2015-08-28 02:41:36 UTC
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On Thu, 27 Aug 2015 22:25:28 -0300, Ajo Wissink
Post by Ajo Wissink
Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
If you have tried to send a message, or have tried to check mail, and
you still get that error message then there must be something else
wrong. I suggest that you pose your question in the Eudora mailing
http://www.listmoms.net/eudora-win/
Ajo
LOL. At first I thought this would be easy until I realized that it
takes an email to join that list. Have to break down and get a gmail
address I guess.

Thanks Ajo.
BK
BobbyK
2015-08-28 15:27:17 UTC
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Post by BobbyK
On Thu, 27 Aug 2015 22:25:28 -0300, Ajo Wissink
Post by Ajo Wissink
If you have tried to send a message, or have tried to check mail, and
you still get that error message then there must be something else
wrong. I suggest that you pose your question in the Eudora mailing
http://www.listmoms.net/eudora-win/
I have successfully joined this list and sent a post. However, I
haven't seen mine but others so far. I don't want to re-post if it
has been distributed. Have you seen it so far?

I may have goofed because I have very little knowledge of Gmail, which
I have to use.

Thanks Ajo.

BK
Ajo Wissink
2015-08-28 16:48:30 UTC
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Post by BobbyK
Post by BobbyK
On Thu, 27 Aug 2015 22:25:28 -0300, Ajo Wissink
Post by Ajo Wissink
If you have tried to send a message, or have tried to check mail, and
you still get that error message then there must be something else
wrong. I suggest that you pose your question in the Eudora mailing
http://www.listmoms.net/eudora-win/
I have successfully joined this list and sent a post. However, I
haven't seen mine but others so far. I don't want to re-post if it
has been distributed. Have you seen it so far?
I may have goofed because I have very little knowledge of Gmail, which
I have to use.
Thanks Ajo.
BK
You should have received a welcome message after sending your request
to join. A first post may take a little time, a few hours perhaps,
because one of the "list moms" who are moderating the list has to
clear you. Your message just appeared! while I am writing this!

Ajo
j***@gmail.com
2015-08-29 11:21:52 UTC
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Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign. Click to select the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
BK
BobbyK
2015-08-29 18:02:02 UTC
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Post by j***@gmail.com
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign. Click to select
the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
Post by Bob Kingsley
"You have never checked (sent) email using an SSL connection ---"
That is the best suggestion yet. Only a couple of problems. I was
able to finally get into the "Certificate Information Manager" again
and work with getting certificates trusted. The first problem is that
I can't get that move saved. Have tried it many times. Then I had to
shut down my computer and now I can't get back to the Cert Info Mgr
again, and the relay personality is unchecked. Will keep at it
though.

Thanks.

BK
j***@gmail.com
2015-08-29 18:52:46 UTC
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After your reboot, you need to try to send an email first before you can re-enter the Cert Info Mgr. I fell into that trap, too.

I'm not sure what you mean by "can't get that move saved". Eudora doesn't move the certificate down to the "trusted" section, curiously enough. At least, it doesn't show it. Maybe it adds it to "trusted", but it keeps it in the top section too, I don't know. Just keep adding each one to "trusted", then it should work.
Post by BobbyK
Post by j***@gmail.com
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign. Click to select
the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
Post by Bob Kingsley
"You have never checked (sent) email using an SSL connection ---"
That is the best suggestion yet. Only a couple of problems. I was
able to finally get into the "Certificate Information Manager" again
and work with getting certificates trusted. The first problem is that
I can't get that move saved. Have tried it many times. Then I had to
shut down my computer and now I can't get back to the Cert Info Mgr
again, and the relay personality is unchecked. Will keep at it
though.
Thanks.
BK
BobbyK
2015-08-29 20:04:02 UTC
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Post by j***@gmail.com
After your reboot, you need to try to send an email first before you can re-enter the Cert Info Mgr. I fell into that trap, too.
I'm not sure what you mean by "can't get that move saved". Eudora doesn't move the certificate down to the "trusted" section, curiously enough.
At least, it doesn't show it. Maybe it adds it to "trusted", but it keeps it in the top section too, I don't know. Just keep adding each one to "trusted",
then it should work.
I meant that even when checking the smiley faces and the untrusted
certs showed as trusted there was no skull and crossbones to check and
save them there.

All is well now. I finally got the skull and crossbones figure,
clicked it and VOILA.

I have to thank AJO for tons of help offline, and you, specifically,
for the long, and simple explanation that helped me get to the
Certification Information Manager.
Post by j***@gmail.com
Post by BobbyK
Post by j***@gmail.com
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign. Click to
select
Post by j***@gmail.com
Post by BobbyK
Post by j***@gmail.com
the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
Post by Bob Kingsley
"You have never checked (sent) email using an SSL connection ---"
That is the best suggestion yet. Only a couple of problems. I was
able to finally get into the "Certificate Information Manager" again
and work with getting certificates trusted. The first problem is that
I can't get that move saved. Have tried it many times. Then I had to
shut down my computer and now I can't get back to the Cert Info Mgr
again, and the relay personality is unchecked. Will keep at it
though.
Thanks.
I\
Ajo Wissink
2015-08-29 22:54:27 UTC
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Post by j***@gmail.com
After your reboot, you need to try to send an email first before you can re-enter the Cert Info Mgr. I fell into that trap, too.
What is a reboot needed for?

Ajo
Ajo Wissink
2015-08-29 19:09:19 UTC
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Post by j***@gmail.com
Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
BK
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign.
If the last one is a smiley face then you have no untrusted
certificates. Only skulls are not trusted.

Apparently your problem is not an untrusted certificate, but something
else. Problems with a connection sometimes make Eudora think there is
something wrong with a certificate. I see that quite often myself.
Satellite is the only way to get internet service where I live and
when it rains too hard or there is too much snow that can cause a
problem.
Post by j***@gmail.com
Click to select
the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
A lot of this did not make much sense, but if it works for you that's
great!.

Ajo
j***@gmail.com
2015-08-29 22:01:01 UTC
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I have to admit that, as I was writing my post, I was going through the steps, so I could make it as clear and complete as possible. At that point, they were all smiley-faces, but, as you pointed out, at least one of them couldn't have been a smiley-face the first time I did it. The first time I tried this, I just went down to the bottom one, and it didn't work. After trying again and failing, I got frustrated and added all of them to the trusted list, and that worked. I agree with you, that doesn't make sense. Maybe more than 1 of them were skulls; I didn't notice. Or, maybe I made some stupid mistake, and thought I was adding the skull to the trusted list when I wasn't. I know my problem wasn't a faulty internet connection. I'm fortunate enough to live in an area where the connection is usually rock solid stable.

But, I'm glad this helped people get Eudora back and working. Gmail has been doing this repeatedly to Eudora users for a few months, but this is the first time Verizon did it. We need to be ready to fix it many more times with Verizon, too.
Post by Ajo Wissink
Post by j***@gmail.com
Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
BK
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign.
If the last one is a smiley face then you have no untrusted
certificates. Only skulls are not trusted.
Apparently your problem is not an untrusted certificate, but something
else. Problems with a connection sometimes make Eudora think there is
something wrong with a certificate. I see that quite often myself.
Satellite is the only way to get internet service where I live and
when it rains too hard or there is too much snow that can cause a
problem.
Post by j***@gmail.com
Click to select
the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
A lot of this did not make much sense, but if it works for you that's
great!.
Ajo
Ajo Wissink
2015-08-29 23:06:26 UTC
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Post by j***@gmail.com
I have to admit that, as I was writing my post, I was going through the steps, so I could make it as clear and complete as possible. At that point, they were all smiley-faces, but, as you pointed out, at least one of them couldn't have been a smiley-face the first time I did it. The first time I tried this, I just went down to the bottom one, and it didn't work. After trying again and failing, I got frustrated and added all of them to the trusted list, and that worked. I agree with you, that doesn't make sense. Maybe more than 1 of them were skulls; I didn't notice. Or, maybe I made some stupid mistake, and thought I was adding the skull to the trusted list when I wasn't. I know my problem wasn't a faulty internet connection. I'm fortunate enough to live in an area where the connection is usually rock solid stable.
But, I'm glad this helped people get Eudora back and working. Gmail has been doing this repeatedly to Eudora users for a few months, but this is the first time Verizon did it. We need to be ready to fix it many more times with Verizon, too.
OK, everybody seems to be happy, regardless of how they managed to
solve their problem!

Gmail is coming out with new certificates that are good for just a
couple of months. I don't see how that can improve secure connections.
What about Verizon? For how long are their new certificates? Is it
as bad as gmail?

Ajo
j***@gmail.com
2015-08-30 00:33:11 UTC
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BobbyK said he had to shut down his machine, but didn't say why. I didn't, but I did exit Eudora a few times because I got interrupted. I didn't mean to make you think I had to reboot, but exiting Eudora reset the "last SSl info", just like BobbyK's reboot.

Oh, could this be? The new certificate says it will expire on Saturday, August 05, 2017! I hope that's really true! But, the incoming certificate expires on Sunday, August 30, 2015. Here we go again!
Post by Ajo Wissink
Post by j***@gmail.com
I have to admit that, as I was writing my post, I was going through the steps, so I could make it as clear and complete as possible. At that point, they were all smiley-faces, but, as you pointed out, at least one of them couldn't have been a smiley-face the first time I did it. The first time I tried this, I just went down to the bottom one, and it didn't work. After trying again and failing, I got frustrated and added all of them to the trusted list, and that worked. I agree with you, that doesn't make sense. Maybe more than 1 of them were skulls; I didn't notice. Or, maybe I made some stupid mistake, and thought I was adding the skull to the trusted list when I wasn't. I know my problem wasn't a faulty internet connection. I'm fortunate enough to live in an area where the connection is usually rock solid stable.
But, I'm glad this helped people get Eudora back and working. Gmail has been doing this repeatedly to Eudora users for a few months, but this is the first time Verizon did it. We need to be ready to fix it many more times with Verizon, too.
OK, everybody seems to be happy, regardless of how they managed to
solve their problem!
Gmail is coming out with new certificates that are good for just a
couple of months. I don't see how that can improve secure connections.
What about Verizon? For how long are their new certificates? Is it
as bad as gmail?
Ajo
Ajo Wissink
2015-08-30 02:29:33 UTC
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Post by j***@gmail.com
BobbyK said he had to shut down his machine, but didn't say why. I didn't, but I did exit Eudora a few times because I got interrupted. I didn't mean to make you think I had to reboot, but exiting Eudora reset the "last SSl info", just like BobbyK's reboot.
You can leave Eudora running. It is the new mail check or the new
attempt to send mail that is resetting the last SSL info.
Post by j***@gmail.com
Oh, could this be? The new certificate says it will expire on Saturday, August 05, 2017! I hope that's really true!
That sounds more reasonable and is what most email servers do.
Post by j***@gmail.com
But, the incoming certificate expires on Sunday, August 30, 2015. Here we go again!
Good luck! ;-)
BobbyK
2015-08-30 03:00:57 UTC
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Post by j***@gmail.com
BobbyK said he had to shut down his machine, but didn't say why.
Nothing to do with the problem, just had to leave the house for a
short time.
Post by j***@gmail.com
I didn't, but I did exit Eudora a few times because I got interrupted. I didn't mean to make you think I had to reboot, but exiting
Eudora reset the "last SSl info", just like BobbyK's reboot.
Oh, could this be? The new certificate says it will expire on Saturday, August 05, 2017! I hope that's really true!
But, the incoming certificate expires on Sunday, August 30, 2015. Here we go again!
NO! Please NO!

I don't understand. Eudora has been rock solid for me in the last 18
years until last week. What's happening?
Pirjo
2016-01-13 22:10:15 UTC
Permalink
Raw Message
Post by j***@gmail.com
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign. Click to select the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
BK
This advice helped me. Thank You! Kiitos!
Micky
2016-01-14 09:28:32 UTC
Permalink
Raw Message
On Wed, 13 Jan 2016 14:10:15 -0800 (PST), Pirjo
Post by j***@gmail.com
Post by j***@gmail.com
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK.
Why was the relay personality box checked in the first place? This
doesn't really make sense to me.

First, the full name of the box is "Use relay personality, if
defined", so if, in Tools/Options/Sending Mail, no relay personality
has been chosen, checking the box doesn't do anything. Nor does
unchecking it.

So if unchecking it did something, that means there was a relay
personality. Why? Either for a good reason or not a good reason.

Possibly not a good reason, because it's possible there was no good
reason but the user misunderstood the setting, or the reason ended and
the selection didn't get changed back to None.

But I think in most cases that someone designated one personality as
the relay personality (the one to be used for sending mail for one or
more *other* personalities) there was a good reason. In my case, one
of my mail servers cancelled my ability to send mail with it, and I
have to use the other one.

So if there is a functioning relay personality, that is the one whose
Last SSL Information should have been clicked on, in
Tools/Personalities/Propeties/Generic Properties. That would not
give the problem message "You have never sent email using an SSL
connection ---" because it's the personality used to send mail.***

But if you temporarily use another personality to send mail, and you
trust the certificates if needed for that personality, then when you
go back to using the Relay Personality, you'll still have to trust the
certificates for that one.

If you give up on using the relay personality entirely, ask yourself
why you were using it in the first place.

***BTW, if the OP got the message "You have never *checked* email
using an SSL connection ---", he's in the wrong Tab. Checking email
is about incoming mail, and it's managed by the Incoming Mail tab.
Sending email uses the Generic Properties tab. You'd be surprised how
many people look in the wrong tab.


And if all this is too much for you, even though it's simple once you
get used to it, you can use Stunnel, a free program, which is sort of
h ard to set up in the first place, but after that you're dne.
Post by j***@gmail.com
Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign. Click to select
the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
Post by j***@gmail.com
Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
BK
This advice helped me. Thank You! Kiitos!
BobbyK
2016-01-14 16:34:20 UTC
Permalink
Raw Message
On Wed, 13 Jan 2016 14:10:15 -0800 (PST), Pirjo
Post by j***@gmail.com
Post by j***@gmail.com
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign. Click to select
the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
Post by j***@gmail.com
Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
BK
This advice helped me. Thank You! Kiitos!
LOL. I still can't receive email, but can send. I read incoming on
my iPhone.
BK
g***@mindspring.com
2018-01-14 02:44:18 UTC
Permalink
Raw Message
Post by j***@gmail.com
Sorry if this post is long, but please bear with me, as doing this made it work for me, and it should work for you, too.
Unchecking "Use relay personality, if defined" is just one step towards fixing the problem. This will only enable you to get into the "Eudora SSL Connection Information Manager". Here's what you do: Go into Personalities, if you're not already there, and select Properties. Uncheck the box for "relay personality". Click OK. Try to send an email, and hit YES when you get the SSL error. Go back into the properties of your personality. THIS TIME, the "Last SSL info" button should get you into the Manager. Now, click on "Certificate Information Manager", and here's where the "fun" begins. At the top, you are presented with the certificates that didn't work, and all the ones that are "trusted". Your job is to add the "untrusted" ones to the "trusted" list. You will see a smiley-face and a + sign at the top of the list. Click on the + sign, and it will open another one like it. Keep clicking each + sign until you get to the last smiley-face with NO + sign. Click to select the last one, then click on the "Add to trusted" button. Click the "Done", then the "OK", then the next "OK". Try to send an email. If this doesn't work, repeat the whole process, including the attempt to send an email. If this still doesn't work, then add each of the "smiley-face +" ones to the trusted list, too. Mine didn't work until I did that last step. I think this will work for everyone out there. I'm glad to see so many other Eudora fans out there!
Post by BobbyK
On Mon, 10 Aug 2015 05:51:09 -0300, Ajo Wissink
Post by Ajo Wissink
On Sun, 9 Aug 2015 20:06:34 -0700 (PDT), Bob Kingsley
Post by Bob Kingsley
Many of us are having the same problem. Click on "Last SSL Info" and get
"You have never checked (sent) email using an SSL connection ---"
I have tried both sending and checking but can not get to the next step. Suggestions please!
You may have a relay personality indicated in the Generic Properties.
In that case you have to do the procedure for that personality.
This has just cropped up with me. When I go to the
Personality/Properties/Generic I see the relay personality checked and
uncheck that, except that I don't have a relay personality. It
doesn't help I still get the "never sent mail using an SSL connection.
BK
OMG!!! This worked for me!!! It used to be that I'd simply have to re-boot the PC and all would be well. Clicking "yes" to the error message never did any good. Thanks to the power of Googling to be able to find this and the many dedicated (stubborn?) Eudora users. I've used Eudora since about 1995 when I first signed up with Mindspring--now Earthlink. Thanks again.
Arwin Vosselman
2015-02-20 09:16:47 UTC
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Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
This problem is also being discussed in the following newsgroup:
<news:xs4all.general>.
--
Regards,
Arwin.
j***@verizon.net
2015-08-28 21:40:38 UTC
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Raw Message
I am having the same problem. I can't access the certificate information manager because when I click in last ssl info it says I never sent mail using an ssl connection. When I try to send mail using an ssl connection it fails, and I still get this message.

Has anyone found a solution to this?
Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
BobbyK
2015-08-28 23:39:18 UTC
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Post by j***@verizon.net
I am having the same problem. I can't access the certificate information manager because when I click in last ssl info it says I never sent mail using an ssl connection. When I try to send mail using an ssl connection it fails, and I still get this message.
Has anyone found a solution to this?
I have spent two full days trying to get this straightened out with no
progress. Even tried another group and no answer. I love Eudora but
may just have to find another email client. The only positive is that
I can still get my email on iPhone, but it's not the same.

BK
Post by j***@verizon.net
Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
Dennis Lee Bieber
2015-08-29 17:42:25 UTC
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Post by BobbyK
I have spent two full days trying to get this straightened out with no
progress. Even tried another group and no answer. I love Eudora but
may just have to find another email client. The only positive is that
I can still get my email on iPhone, but it's not the same.
1) the "SSL Info" button exists for each personality that can send
email... You'd have to check each of them to find a potentially locked one
AFTER doing a SEND.

2) the POP3 (receiving) page also has "SSL Info" which is separate from
the SMTP (sending) page... You may have to check that for all personalities
that have receiving capability to find the bad one.
--
Wulfraed Dennis Lee Bieber AF6VN
***@ix.netcom.com HTTP://wlfraed.home.netcom.com/
j***@gmail.com
2015-08-29 20:20:44 UTC
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Raw Message
Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
thank you! after days of Googling and tweaking with no success, this worked beautifully.
r***@cox.net
2018-01-13 04:19:18 UTC
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Raw Message
Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
i love you people! eudora must appeal to a great group of humans. i have lost most of the week dealing with this & now all is fine.
c***@gmail.com
2018-01-30 18:59:00 UTC
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Raw Message
Post by r***@cox.net
Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
i love you people! eudora must appeal to a great group of humans. i have lost most of the week dealing with this & now all is fine.
When you get the certificate error as you try to send you need to click Yes for trusted. Then do it again and click Yes again and so forth... after a few tries this will populate the certificate history and when you go to tools>options>checking mail (or similar for personality) and click the Last SSL Info button you should no longer get the "you've never done any SSL..." message.
If you still do then keep trying the send, and clicking Yes on the SSL error message.

Perhaps you know the next steps but I put them here in case not:
Click the Last SSL Info Button
Click on Certificate Information Manager
Under the Server Certificates click on the + sign to expand and keep clicking + signs til you get to the bottom
The bottom one will be a skull icon (for untrusted); highlight this skull and then click the Add to Trusted button.
Click Done, OK and close out of everything.

(This worked for me 1/26/2018 after cox changed their email security stuff)
c***@nym.hush.com
2018-01-31 06:07:46 UTC
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Raw Message
Post by c***@gmail.com
Post by r***@cox.net
Post by zazie
I have an issue with SSL certificates (Eudora 7.1.0.9, win 8).
Apparently, my provider changed certificates; I know how to add the (new) certificate to "trusted certificates" but I cannot get into the manager: "you have never sent mail using an SSL connection with this personality since the last time you started Eudora" (and since I am not able to send messages due to the certificate problem, I am afraid I am caught in a loop).
Does anyone know how to deal with this? Hope so .... Zazie
i love you people! eudora must appeal to a great group of humans. i have lost most of the week dealing with this & now all is fine.
When you get the certificate error as you try to send you need to click Yes for trusted. Then do it again and click Yes again and so forth... after a few tries this will populate the certificate history and when you go to tools>options>checking mail (or similar for personality) and click the Last SSL Info button you should no longer get the "you've never done any SSL..." message.
If you still do then keep trying the send, and clicking Yes on the SSL error message.
Click the Last SSL Info Button
Click on Certificate Information Manager
Under the Server Certificates click on the + sign to expand and keep clicking + signs til you get to the bottom
The bottom one will be a skull icon (for untrusted); highlight this skull and then click the Add to Trusted button.
Click Done, OK and close out of everything.
(This worked for me 1/26/2018 after cox changed their email security stuff)
I had to do the following:

Under Getting Started --- SMTP Server Outgoing I had to check the Allow
authentication box.

Under Checking Mail Secure Socket When Receiving I had to select If
Available, Starttls.

Under Sending Mail I had to check the following boxes: Allow Authentication
& use Submission port 587. I also had to set Secure Socket when sending to
NEVER.

I got an error when going to the Certificate Manager. The current
certificate was set for smtp.cox.net. The configuration in my Eudora.ini
was smtp.west.cox.net. That mismatch caused authentication of the
certificate to fail. I removed the 'west' from the Eudora.ini parameter,
went to the certificate manager again and followed the steps you outlined it
finally started to work.

I an extremely happy. I've been using Eudora Pro since the beginning and
would hate to trash it and start using another email program.

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