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Mac Forum / Applications / Eudora / May 2008



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Can't Send Mail

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Charles H. Sampson - 13 May 2008 07:06 GMT
I know there have been a number of threads recently on the above
subject, but none of them seems to apply to my case.

    I'm running OS X 10.4.11 and Eudora 6.2.4 on a G4.  What is
somewhat unusual is that my DSL provider, AT&T, is not my ISP.  (I'll
supply the history of that if necessary, but I think it's irrelevant.)

    Using Eudora has been uneventful until recently, when AT&T made
some changes designed to cut down on outgoing spam.  They added SSL
password authentication for sending messages and sending through a
special port.  In addition, if I want to send using a return address
that is not my login address with them, I have to register that address
with them and have them verify that it is a legitimate address.  Another
complication is that I signed up for DSL with Bell South before they
were taken over by AT&T, so my login address is an sbcglobal.net
address.

    I've done the registering and verifying bit for the four addresses
we use.  With AT&T's help, I got Mac Mail working.  Then I tried to
transcribe what I learned from that to Eudora.  (AT&T doesn't support
Eudora, but they actually worked with me for a couple of hours trying to
get it going.)  The port can be specified a couple of ways, one being
following the name of the SMTP server name with a colon and the port
number, on the Getting Started settings display.  The email address for
the SMTP server is what is displayed after the colon in Mail's Outgoing
Mail Server (SMTP) specification.  I went so far as to change the
passwords on all of our mail accounts to be the same.  On the SSL
setting display, I set SSL for SMTP to Required (TLS).

    With these settings, when I try to send a message, there is a
longish  pause after which the Task Progress window shows "TCP/IP Error.
-3162; The server is not responding."

    I hope somebody knows what to do.  Currently we're limping along
using Mail for outgoing and Eudora for incoming.  Of course I could
change to Mail but that would involve sending change of address notices
to all of our correspondents.  Besides, I just prefer Eudora.

                       Charlie
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Patty Winter - 13 May 2008 08:25 GMT
>     With these settings, when I try to send a message, there is a
>longish  pause after which the Task Progress window shows "TCP/IP Error.
>-3162; The server is not responding."

I did a search for "3162" on the Eudora tech support site and found
this:

http://eudora.com/techsupport/kb/2444hq.html

Although it doesn't mention AT&T on that page, the FAQ page that
leads to it does:

http://eudora.com/techsupport/mac/faq/

Patty
Charles H. Sampson - 14 May 2008 06:52 GMT
> >     With these settings, when I try to send a message, there is a
> >longish  pause after which the Task Progress window shows "TCP/IP Error.
[quoted text clipped - 11 lines]
>
> Patty

    Thanks.  I had already found that page by much the same route you
used.  Unfortunately, the article basically says, "It's not Eudora's
fault.  It's the Server's."  I can't make that fly because the server
works just fine when the mail's coming out of Mac Mail.

    I'm still hoping that I've got some parameter wrong somewhere.

                       Charlie
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Patty Winter - 14 May 2008 07:15 GMT
>     Thanks.  I had already found that page by much the same route you
>used.  Unfortunately, the article basically says, "It's not Eudora's
>fault.  It's the Server's."  I can't make that fly because the server
>works just fine when the mail's coming out of Mac Mail.

Oh, okay, sorry. I thought that was with a different mail server.
I see now that AT&T isn't your ISP, so you aren't using their
mail server and thus that article I found isn't relevant.

Patty
Sander Tekelenburg - 15 May 2008 16:38 GMT
[...]

> the article basically says, "It's not Eudora's
> fault.  It's the Server's."  I can't make that fly because the server
> works just fine when the mail's coming out of Mac Mail.

That means absolutely nothing. 95% of the time when you view a web page,
you're looking at a broken[*] document/server that the browser 'fixes'
in order to p[resent you with something usable. That fix is basically
guesswork, different in each browser. Thus it totally flies that a
(broken) web page 'works' in one browser and not in another.

My impression is mail servers suffer less from such  brokenness, but are
not perfect either. So it may very well be that one mail client
(Mail.app) 'works' with a broken server while some other client (Eudora)
does not. Not Eudora's fault.

Not that this necessarily applies to your particular problem -- it
applies to your debugging logic ;)

[*] "Broken" in the sense that it does not adhere to the relevant
standard(s).

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Sander Tekelenburg, <http://www.euronet.nl/~tekelenb/>

Mac user: "Macs only have 40 viruses, tops!"
PC user: "SEE! Not even the virus writers support Macs!"

Daniel Cohen - 13 May 2008 22:00 GMT
>      I know there have been a number of threads recently on the above
> subject, but none of them seems to apply to my case.
[quoted text clipped - 19 lines]
> passwords on all of our mail accounts to be the same.  On the SSL
> setting display, I set SSL for SMTP to Required (TLS).

Have you tried setting SSL to Required (Alternate Port)?

I ask because in a different situation that was what I needed to do.

I'm not sure if you would also need to adjust things in the Ports and
Protocols section of the Settings. I also can't remember if that is in
the default collection of settings. I think you may have to
installEsoteric Settings to get that.

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John H Meyers - 16 May 2008 05:37 GMT
> Using Eudora has been uneventful until recently, when AT&T
> made some changes designed to cut down on outgoing spam.
> They added SSL [and] password authentication for sending messages
> and sending through a special port.

Generally your "User Name" (login) for AT&T should be your full,
"home account" email address, e.g.: myself@sbcglobal.net
(or whatever it is in working Mac Mail)

Probably the only gap in transfering Mac Mail settings to Eudora
is in the port numbers, which is basically a user interface (GUI)
and documentation gap in Eudora -- the only email program
which considers actual port numbers in use as if "Top Secret" info,
never to be disclosed to any user :)

At the risk of violating the Official Secrets Act:

Incoming/Outgoing port numbers and SSL settings for any ISP
correspond to Eudora's "Secure Sockets" options,
within each Personality's "Properties" (Windows)
or under the separate "SSL" settings (Mac):

Incoming -> set "Secure Sockets while Receiving"
(or "SSL for POP/IMAP") for the given personality to:
Port 110 (or 143) and no SSL -> "Never" (None)
Port 110 (or 143) with SSL -> "Required, [START]TLS"
Port 995 (or 993) with SSL -> "Required, Alternate Port"

Outgoing -> set "Secure Sockets while Sending"
(or "SSL for SMTP") for the given personality to:
Port 25 (or 587) and no SSL -> "Never" (None)
Port 25 (or 587) with SSL -> "Required, [START]TLS"
Port 465 with SSL -> "Required, Alternate Port"

If the ISP specifies outgoing port 587,
then also check-mark "Use submission port (587)"
otherwise be sure to clear that check box
for the given Personality (under "Personalities" in Mac)

Note that outgoing (SMTP)
"Alternate Port" (465) and "Submission Port" (587)
can not both be used at the same time,
so don't specify both things for the same personality.

Finally, be sure to always check-mark "Allow authentication"
for all SMTP servers requiring authentication (login for sending).

Problems:

No connection:

Wrong port, firewall/ISP block, Anti-virus/spy (disable mail scanners),
wrong "Esoteric" default ports, wrong "overrides" of built-in default ports.

SSL problem: SSL (vs. "587") settings, Anti-virus (disable mail scanning)

POP login fails and SMTP auth fails: wrong "User Name"
(try adding or removing "@somewhere.net" in "User Name" field)

If the connection problem persists and it's not obvious what's wrong,
use built-in logging to get necessary data for exact diagnosis.

--
Charles H. Sampson - 20 May 2008 07:00 GMT
I finally got it working, although I'm not quite sure what's going
on.  Since this might help some other Eudora/Mac user, I'll explain.

    Recall the situation.  I have two ISPs.  One of them, AT&T, I'm
treating as just the supplier of my DSL connection, but AT&T is
technically an ISP and, if I understand things correctly, they are
responsible for handling my outgoing mail.  Incoming mail is delivered
to my old ISP, from whom I retrieve it.  My problem arose when AT&T put
into place a bunch of things to cut down on outgoing spam, specifically
SSL and a non-standard port

    The solution was to nearly ignore AT&T.  For my SMTP server, I gave
my old ISP's server.  I did however check "Allow authorization" on the
"Sending Mail" settings window.  On the "Ports & Protocols" window, I
entered AT&T's special SMTP port.  On the "SSL" window, I selected
"Required (Alternate Port)" for "SSL for STMP:" and "Maximum
Compatibility" for "Alternate Port SSL Negotation".  I did the same for
"SSL for IMAP:" and "Standard Port SSL Negotation", which probably
doesn't matter but I'm not inclined to experiment any more right now.
Finally, I made all of the mail passwords the same.  Early on, I entered
at AT&T's website all of the return addresses I was going to use and had
them verified.

    I haven't been able to make out from the log file what's going on.
If anybody's interested, I'll post an extract.

                       Charlie
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Patty Winter - 20 May 2008 07:36 GMT
>     Recall the situation.  I have two ISPs.  One of them, AT&T, I'm
>treating as just the supplier of my DSL connection, but AT&T is
>technically an ISP and, if I understand things correctly, they are
>responsible for handling my outgoing mail.  

Only if you want them to be. Otherwise, you can just use your other
ISP's mail server. For example, I have a cable modem from Comcast,
but I rarely use my Comcast email account. Mostly I just use the
cable modem as a conduit to my "real" ISP. It's the latter's mail
servers (POP and SMTP) that I use for incoming and outgoing mail.

> My problem arose when AT&T put
>into place a bunch of things to cut down on outgoing spam, specifically
>SSL and a non-standard port

Another technique that ISPs use is called "POP Before SMTP." That
means that you must identify yourself as someone who has a POP
account with that ISP before you can send mail through their servers.
My ISP implemented that some time ago. I don't actually have to POP
my mail before each time I want to send mail. (Although I usually do.)
The record of my POP session lasts for hours (or longer?), keeping me
authorized to send mail.

Anyway, just a couple more ideas that might be useful to someone!

Patty
 
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