Settings for Eudora 7 for using a smarthost

Can anybody explain or post a link to a page explaining how to set up
Eudora 7 to use a smarthost?
--

Alfred Molon
http://www.molon.de - Photos of Asia, Africa and Europe

On Sat, 23 Aug 2008 08:13:50 -0500, Alfred Molon wrote:

> Can anybody explain or post a link to a page explaining
> how to set up Eudora 7 to use a smarthost?

A "smarthost," as the term is conventionally used,
is just an SMTP server (although it often means
a "forwarding" server used by another SMTP server).

Eudora uses whatever SMTP server(s) you tell it to use, per personality.

If you give an example of what you are trying to accomplish,
perhaps the details for accomplishing it can then better be discussed.

http://en.wikipedia.org/wiki/Smart_host

--

There's a chance that what is meant is simply this:

Personality "A" receives POP mail for domain "A,"
but wants to send mail via an unrelated SMTP server
which requires "authentication,"
via a different username/password than POP server "A."

Solution:

Set up personality "B" with the alternate SMTP server info,
including its username/password for authentication.

Choose personality "B" as the "SMTP relay personality"
in the main "Sending mail" settings.

Mark "Use relay personality" in personality "A"s "properties"
(right click "A" in the "Personalities" window and choose "Properties")

Now when you send mail for the "A" personality,
it will use the alternate SMTP server and username/password/etc.

--

In article <op.ugco5rqtnn735j@miu.edu>, John H Meyers says...
> On Sat, 23 Aug 2008 08:13:50 -0500, Alfred Molon wrote:
>
> > Can anybody explain or post a link to a page explaining
> > how to set up Eudora 7 to use a smarthost?
>
> A "smarthost," as the term is conventionally used,
> is just an SMTP server (although it often means
> a "forwarding" server used by another SMTP server).
>
> Eudora uses whatever SMTP server(s) you tell it to use, per personality.
>
> If you give an example of what you are trying to accomplish,
> perhaps the details for accomplishing it can then better be discussed.
>
> http://en.wikipedia.org/wiki/Smart_host

I've sent email with Eudora 7 while the computer was connected to the
Internet through a mobile phone (using GSM mobile data services). The
email bounced back, because the recipient was using a
barracudacentral.com service which identified the IP address of my
mobile phone provider as having a poor reputation.

I posted the problem to the German newsgroup about mobile communications
and somebody suggested to use a "smarthost".

I asked my webspace provider and they said that my SMTP server is
already a smarthost and that I just need to set up the email software
accordingly. Apparently I have to authenticate myself before sending
emails.

What I don't know is if I have set up Eudora properly. In any case, the
purpose of the exercise is to reduce the number of sent emails which are
blocked by spam filters.

Sometimes I have the impression that when I am using a WLAN hotspot or
GSM mobile data services to send emails, the emails do not arrive. I
also have the impression that WLAN hotspots exchange the SMTP servers: I
specify the SMTP server of my host, but perhaps the WLAN service changes
that to the SMTP server of the WLAN provider.

I also remember that in one case, while I was travelling in France last
month, I was unable to send emails through the WLAN hotspot of a hotel.
No idea if this was caused by the firewall of the internet service of
the hotel or by something else.

In any case, the general problem is sending emails while travelling.
Sometimes I'm unable to send emails (but I can receive them and surf the
web) and sometimes the emails are blocked by some spam filter.
--

Alfred Molon
http://www.molon.de - Photos of Asia, Africa and Europe

On Sat, 23 Aug 2008 13:57:04 -0500, Alfred Molon wrote:

> I've sent email with Eudora 7 while the computer was connected to the
> Internet through a mobile phone (using GSM mobile data services).
> The email bounced back, because the recipient was using a
> barracudacentral.com service which identified the IP address
> of my mobile phone provider as having a poor reputation.

If you did not make any adjustment to your Eudora SMTP settings,
but just changed your computer to connect to the internet via your phone,
then you are probably correct that the server you had told Eudora to use
was not actually used, because of an intercept by your mobile provider:

> Sometimes I have the impression that when I am using a WLAN hotspot
> or GSM mobile data services to send emails, the emails do not arrive.
> I also have the impression that WLAN hotspots exchange the SMTP servers:
> I specify the SMTP server of my host, but perhaps the WLAN service changes
> that to the SMTP server of the WLAN provider.

Some networks "proxy" the SMTP service on the most common ports,
so that no matter what SMTP server name (or IP address) you supply,
they may indeed route it through their own servers;
all email clients are affected the same by any such proxying.

This neatly "solves" one common and annoying problem,
which is that of travelers who otherwise might find that their "home"
SMTP settings can not even initially connect from elsewhere,
who now just don't have to care, as the mail "goes right out" anyway.

However, if your network provider is suspected of harboring spammers,
then that very same "convenience" may turn into a different problem,
in which your messages are initially accepted from your computer
with no problem, until they get to their destination,
where an anti-spam system rejects them instead

If this is the case, try discussing it with your network provider.

Message recipients (which can be yourself) can track how messages
were actually routed by examining all the incoming "Received:" headers,
each of which is like a "postmark" saying that "this message arrived
at [this server], having just come from [that server or originator]"

> I asked my webspace provider and they said that my SMTP server is
> already a smarthost and that I just need to set up the email software
> accordingly. Apparently I have to authenticate myself before sending
> emails. What I don't know is if I have set up Eudora properly.

If the ISP's instructions and your settings were both completely known,
then that could be determined.

Successful sending (and final receipt by addressees) while using a normal,
non-proxying network would usually demonstrate correct settings, however.

> I also remember that in one case, while I was travelling in France last
> month, I was unable to send emails through the WLAN hotspot of a hotel.
> No idea if this was caused by the firewall of the internet service of
> the hotel or by something else.

Firewalls often block particular ports; most private networks and ISPs
block sending on SMTP port 25 from inside the network to any "outside" server,
because unauthenticated port 25 is a very wide open door for spamming;
the policies of network administrators regarding other ports
(and whether or not they supply a local alternate SMTP server for you)
may vary all over the map, so you just have to ask each one.

> In any case, the purpose of the exercise is to reduce
> the number of sent emails which are blocked by spam filters.

Sometimes the problem is with extremely over-zealous "spam filters,"
which make up for their poor performance at discriminating real spam
by adopting "shotgun" policies that also block vast amounts of non-spam.

Yahoo, for example, within the past year, went so far in that direction
that the problem of legitimate mail never arriving
became greater, for many users, than the former problem
of a percentage of all mail being spam.

Our university, in particular, was unable for quite some time
to communicate with either applicants or existing students who used Yahoo,
so we encouraged all of them to switch promptly to Gmail.

Gmail does the most accurate spam filtering we know of
for any "free account" provider, as well as letting the end user
make the final decision about suspected spam, rather than
even refusing to accept SMTP connections from us in the first place
(that's what Yahoo did, causing our own SMTP server
to "overflow" with an unsent mail backlog, hence drastically slowed
down our mail to all the rest of the world as well -- gee,
Yahoo, did we forget to thank you for acting like that?)

> In any case, the general problem is sending emails while travelling.

Try an SMTP server that uses SSL (on port 465),
which is the least affected by common firewalls and proxies,
and also talk to each other provider (mobile phone, hotel, etc.),
because the world does not have a single solution for all locations,
much as there is nothing else that works the same world-wide.

There are also vendors of remotely accessible SMTP services,
if your "home ISP" does not provide an "everywhere accessible" SMTP server,
but those might still be blocked in some places.

As to setting up Eudora in particular, there is nothing special;
you just specify the "best" SMTP server you can find,
as with any other email client on your own computer.

One easy solution to overcome any email "port problems"
is to use a web site to send your mail, whenever your local client can't.

Web sites which will send your mail include your own ISP's "webmail"
(now offered by most ISPs), or any external service like Gmail,
at which you can now "send mail as" other addresses of your own
(after a simple one-time "confirmation" process).

To enable Eudora to save a copy of mail sent from a web site,
you can "Bcc" a copy to yourself.

I personally actually have all my local mail forwarded
to a dedicated Gmail account, which I then use as my POP server
in place of my original ISP's POP server. I can also use Gmail's
free SMTP server (which uses SSL on port 465, and inserts no
gratuitous advertising into sent mail). With this simple
arrangement, I also get free spam filtering, free "webmail"
(my own Gmail account online), and free backup.

A related article (with good ideas, but some outdated "broken links"):
http://www.nber.org/REASON-FOR-REJECTION/smarthost.html

--

In article <op.ugcy2ebcnn735j@miu.edu>, John H Meyers says...
> Try an SMTP server that uses SSL (on port 465),
> which is the least affected by common firewalls and proxies,
> and also talk to each other provider (mobile phone, hotel, etc.),
> because the world does not have a single solution for all locations,
> much as there is nothing else that works the same world-wide.

Thanks for the informative post. I contacted my host and they said that
they have TLS on port 995. Is this also ok, since you mentioned SSL on
port 465?

I also gave a look at my Eudora settings. "Secure sockets when sending"
was set to "If available, STARTTLS". Under "Last SSL info" there was a
message that SSL had never been used before.

So I set it to "Required, STARTTLS" and sent a mail. Then I had a look
at "Last SSL info" and found the following:

--------------------------------
Server IP address: <IP address of my mailserver> Port: 25
....
....
Security parameters
Negotiation status: Succeeded
SSL version: TLS1
Cipher suite information
.....
Encryption algorithm: EHD-RSA-DES- ......
.....
Notes
Certificate bad: Destination host name does not match host name in
certificate
But ignoring this error because Certificate is trusted.
-----------------------------------

Clicking on "Certificate Information Manager" gives a load of details,
which I can post if necessary.

So what is happening? I'm using SSL, but on port 25? How is this
possible?

And what could possibly be wrong with the certificate?

On the "Certificate Information Manager" page there is a button "Import
certificate". Do I need to import a certificate here? Where do I get it
from?
--

Alfred Molon

Replying to myself. I found out what causes one part of the problem. The
mailserver I use has a certain name, but it appears that this name is
just an alias and the real SMTP server I'm using (and to which the
certificate is issued) is using a different name. I've replaced the
alias with the real name and now, after sending a mail, under "Last SSL
info" there is no more the error note that the certificate is bad.

However, the Last SSL info shows that port 25 was used. How is this
possible? If SSL was used, shouldn't port 465 or 995 have been used?
--

Alfred Molon

On Sun, 24 Aug 2008 13:46:08 -0500, Alfred Molon wrote:

> The Last SSL info shows that port 25 was used. How is this possible?
> If SSL was used, shouldn't port 465 or 995 have been used?

465 is only for SMTP, and 995 only for POP (993 only for IMAP);
this already shows how confused things are,
and perhaps explains why Eudora steered away
from even talking about or displaying port numbers,
although this turned out to be a frustration for ISP customers,
once their ISPs abandoned "support" for Eudora settings,
leaving users with no idea what to do now,
as well as no way to visually see and confirm
the port number which their settings will choose,
to try to match up with ISP port-oriented instructions --
such is the price of "hearing a different drummer

Here's my attempt at a "Rosetta stone" for this issue:

Each email protocol (POP, IMAP, SMTP) is,
by internet conventions,
associated with only two port numbers,
the higher-numbered of which is _only_ for SSL/TLS,
but the original port number can be used
for _either_ non-SSL or SSL/TLS traffic.

Eudora automatically chooses the port number
which matches your "Secure sockets" choice
(just not exactly as you are expecting,
because the "Alternate Port" is the higher number,
and the "STARTTLS" port is the original number

When a new convention became popular
for email clients to use port 587 for SMTP servers
that were specifically intended for direct client submission,
rather than also for forwarding between "post offices,"
this additional "check box" was added to Eudora as well (since 6.2.3),
now supporting SMTP on three standard port numbers.

The precise relationship between Eudora settings,
port numbers, and SSL/TLS is detailed here:

Setting "Port numbers" in Eudora (Windows and Macintosh)
http://eudorabb.qualcomm.com/showpost.php?p=37616

It is also possible to use any non-standard port numbers in Eudora,
but only via directly editing the options file (Eudora.ini)

If your settings cause port 25 to be used for SMTP,
whether with or without SSL/TLS,
it is likely that you will not be able to contact
any SMTP server outside of the network on which you connect
to the internet, because firewalls usually block outgoing port 25
to other networks (some ISPs will unblock individual subscribers
on request, if they convince the ISP that they need this unblocked
to reach some SMTP server at their external "domain host," etc.)

If your settings use SSL for SMTP on port 465, or use port 587 either way,
there is a greater likelihood that you won't be similarly blocked
(except right where I am, where the firewall administrator
wears a green beret, camouflage jacket, and patrols the perimiter
24 hours per day while carrying an assault rifle

As to "SSL vs. TLS," TLS is basically just a minor update of SSL,
and Eudora uses one library which should cover everything.

References for details about SSL/TLS:
http://en.wikipedia.org/wiki/Secure_Sockets_Layer
http://technet.microsoft.com/en-us/l.../cc784450.aspx

Farther and wider:
http://en.wikipedia.org/wiki/Rosetta_Stone
http://www.mnsu.edu/emuseum/prehisto...ettastone.html
http://www.britishmuseum.org/explore...tta_stone.aspx

--

In article <op.uget4lsxnn735j@miu.edu>, John H Meyers says...

> If your settings cause port 25 to be used for SMTP,
> whether with or without SSL/TLS,
> it is likely that you will not be able to contact
> any SMTP server outside of the network on which you connect
> to the internet, because firewalls usually block outgoing port 25
> to other networks

I have a website and am using the mailserver of the host. The ISP I am
using to connect to my mailserver is always outside the network of the
host, so according to your mail I would never be able to send emails
through the mailserver of my host, or did I misunderstand you?

In the meantime I realised that Eudora 7 uses StartTLS which apparently
builds encrypted connections on Port 25 (unless I misunderstood
something). Is this indeed the case?

My host told me that they block port 465 and that I should use port 995.
But Eudora refuses to send on port 995. I sent another email to my host
to clarify this port issue.
--

Alfred Molon

On Sun, 24 Aug 2008 16:52:00 -0500, Alfred Molon wrote:

> I have a website and am using the mailserver of the host. The ISP I am
> using to connect to my mailserver is always outside the network of the
> host, so according to your mail I would never be able to send emails
> through the mailserver of my host, or did I misunderstand you?

Blocking of port 25 between a local network and the "outside world"
is up to each network and ISP; it's pretty rare not to be blocked
by default, but perhaps it's already been arranged with your "usual" ISP.

If your hosting company is actually on the same network as your ISP,
that might also change things.

You mentioned that you can't connect from various spots while traveling;
if the attempt to connect is always on port 25,
it is generally not surprising when that port turns out to be blocked.

It's sometimes more surprising when it turns out _not_ to be blocked,
but as I think you already noted, there are some providers
(some fancier hotels, perhaps your GSM provider) who may proxy that traffic,
diverting it all to their own SMTP servers, if they want
to offer that as a wonderful selling point for their service.

We block _incoming_ port 25 to our unauthenticated internal SMTP server,
and our manager was quite perturbed when he was able to use that server
with his "home" laptop settings while traveling, until we were able
to show him that his hotel was performing that apparent miracle,
rather than our network letting him through

> In the meantime I realised that Eudora 7 uses StartTLS

That's of course under your control, not "automatically"

> which apparently builds encrypted connections on Port 25
> (unless I misunderstood something). Is this indeed the case?

STARTTLS (under "while Sending") would normally use port 25
unless "Use 587" is check-marked, in which case it would use 587.

"Use 587," in turn, would normally use 587,
unless "Alternate Port" is selected,
which trumps "Use 587" and would instead use 465

Do you see any "Ports" category in your options?
If so, that "Esoteric" plugin can further mess with all defaults,
as can manual edits of Eudora.ini which would not show up anywhere
in the settings interface, so the most through inspection would be
to examine all lines in "Eudora.ini" which contain the string "port"
(perform a case-insensitive search).

File "Eudora.log" would, if set to log these events, also demonstrate for sure
which ports were being used for any actual connections.

> My host told me that they block port 465 and that I should use port 995.

By "my host" do you mean an external web hosting company
(kasserver.com ?), describing their POP and SMTP services,
rather than any ISP speaking about what their firewall blocks outgoing?

Is that an exact quote of what they said?

The language of that sentence is just a bit suspicious to me,
because a server isn't usually described as "blocking" any ports;
rather, it is described as having services listening on specific ports,
and any ports on which it isn't listening will simply not respond
(or may default to "refusing" connections).

Also, in the generally recognized list of internet port numbers,
which fall into various classes:
http://www.iana.org/assignments/port-numbers
you will find only these sanctioned uses of port 995:
pop3s 995/tcp pop3 protocol over TLS/SSL (was spop3)
pop3s 995/udp pop3 protocol over TLS/SSL (was spop3)

> But Eudora refuses to send on port 995

How did you try to tell Eudora to send mail on port 995?
(it's not impossible to actually force it to try SMTP on port 995,
but that's not usually what this could possibly mean).

There is actually a provision for POP servers (which use port 995 for SSL/TLS)
to optionally accept commands for sending mail -- if that's what your hosting
company meant; however, I would think they would have clarified that.

It's also a very rare thing, because it's a rare email client
which is even written to accommodate this rare facility.

This is the setting, FWIW (it becomes a "link" when in a Eudora message,
and can be clicked on while holding [Alt] on the keyboard):

X-Eudora-Option:UsePOPSend

Further description is in your user manual, and in built-in Eudora "Help,"
and at: http://www.eudora.com/techsupport/ini.html

I have no idea whether this is still effective, or how it either
interacts with or might ignore a personality's SMTP settings.

When you use a hosting company's server, you have to find out
what it's specific specs are, which are often unpublished;
another alternative is to use SMTP servers provided by
one's own astute "home" ISP, which are ever more commonly
offering "use from anywhere" SMTP servers,
or you can use Gmail's (free, but not for huge volume),
or any other -- nothing stops one from using
any independent server that will let one log on and send,
and that one's immediate location or connection
isn't blocking (outbound) with a firewall;
it need not have any relation to one's POP account or web host.

Statistics on one web hosting company:
http://www.webhosting.info/webhosts/.../KASSERVER.COM
http://whois.domaintools.com/kasserver.com

--