SSL required, alternate port IMAP SSL problem

[Eric Thomas]

I've seen this posted a couple of other times in this group, but none
of the threads have any answers. They were posted at least a year ago,
so I was hoping someone found a solution since.

I'm running Eudora 6 and I need to use IMAP with SSL using port 993. I
set my "Secure Sockets when Receiving" drop-down menu to "Required,
Alternate port". When I connect, I receive: "IMAP command has failed.
Reason: IMAP connection to server <my server name> has been broken."

Some of the previous threads have suggested that the certificate
involved is not being accepted by Eudora. This was usually associated
with Eudora 5.x. They suggest looking at and modifying the accepted
certificate list. This is done by clicking "Last SSL Info button"
under Options|Checking Mail.

However, when I do that, I get the following message: "You have never
checked mail using an SSL connection with this personality since the
last time you started Eudora (or a negotiation is in progress with
this personality)." Clicking OK on this message box brings me back to
the Options|Checking Mail window, without showing any information
about certificates.

BTW, if I set the drop-down menu to anything else, I get a "Connection
Timed out" message, cause my server doesn't use the other ports.

Thanks in advance,

Eric

[Peter Beattie]

Post by Eric Thomas
I'm running Eudora 6 and I need to use IMAP with SSL using port 993. I
set my "Secure Sockets when Receiving" drop-down menu to "Required,
Alternate port". When I connect, I receive: "IMAP command has failed.
Reason: IMAP connection to server <my server name> has been broken."

That could mean your imap server didn't even respond, or that it did,
only with something that Eudora didn't understand. To see whether it
responds at all at this port, try this at the command line (cmd.exe, if
you're running W2K or XP):

telnet imap.server.com 993

If the command line box's screen changes to black, that would mean the
server at least listens on port 993. Otherwise, you would get

Establishing connection to imap.server.com...

or some such.

Post by Eric Thomas
They suggest looking at and modifying the accepted
certificate list. This is done by clicking "Last SSL Info button"
under Options|Checking Mail.
However, when I do that, I get the following message: "You have never
checked mail using an SSL connection [...]"

Just checked. Although I was clearly connected to the imap server
through port 993, with the setting "Required, Alternate Port", and the
firewall showing Eudora to be connected to port 993 of my imap server,
the "Last SSL Info" button still says that I have never checked mail
using SSL. Looks just like a bug to me...

[Luca Simone]

Same behaviour. 6.0022.
The only strange thing is that I managed to have it working during the
first installation. Now my Eudora "remember" the SSL user certificates
though I cannot access the SSL Negotiation button any more.

I sent a bug report to Eudora.com

Post by Peter Beattie

Post by Eric Thomas
I'm running Eudora 6 and I need to use IMAP with SSL using port 993. I
set my "Secure Sockets when Receiving" drop-down menu to "Required,
Alternate port". When I connect, I receive: "IMAP command has failed.
Reason: IMAP connection to server <my server name> has been broken."

That could mean your imap server didn't even respond, or that it did,
only with something that Eudora didn't understand. To see whether it
responds at all at this port, try this at the command line (cmd.exe, if
telnet imap.server.com 993
If the command line box's screen changes to black, that would mean the
server at least listens on port 993. Otherwise, you would get
Establishing connection to imap.server.com...
or some such.

Post by Eric Thomas
They suggest looking at and modifying the accepted
certificate list. This is done by clicking "Last SSL Info button"
under Options|Checking Mail.
However, when I do that, I get the following message: "You have never
checked mail using an SSL connection [...]"

Just checked. Although I was clearly connected to the imap server
through port 993, with the setting "Required, Alternate Port", and the
firewall showing Eudora to be connected to port 993 of my imap server,
the "Last SSL Info" button still says that I have never checked mail
using SSL. Looks just like a bug to me...

[Dale Wiggins]

Post by Peter Beattie

Post by Eric Thomas
I'm running Eudora 6 and I need to use IMAP with SSL using port 993. I
set my "Secure Sockets when Receiving" drop-down menu to "Required,
Alternate port". When I connect, I receive: "IMAP command has failed.
Reason: IMAP connection to server <my server name> has been broken."

That could mean your imap server didn't even respond, or that it did,
only with something that Eudora didn't understand. To see whether it
responds at all at this port, try this at the command line (cmd.exe, if
telnet imap.server.com 993

Yes, this does sound like a connection could not be established. If
the SSL handshake failed Eudora should have reported an SSL failure
with an error code to indicate what went wrong.

Post by Peter Beattie

Post by Eric Thomas
They suggest looking at and modifying the accepted
certificate list. This is done by clicking "Last SSL Info button"
under Options|Checking Mail.
However, when I do that, I get the following message: "You have never
checked mail using an SSL connection [...]"

Just checked. Although I was clearly connected to the imap server
through port 993, with the setting "Required, Alternate Port", and the
firewall showing Eudora to be connected to port 993 of my imap server,
the "Last SSL Info" button still says that I have never checked mail
using SSL. Looks just like a bug to me...

Yes, there is a known issue with how (in)frequently Eudora updates
certain pieces of information regarding IMAP connections so you may
see cases where Eudora is reporting out of date settings for IMAP.
This is being looked into.


-Dale