Discussion:
Sending mail through TOR/Socks
(too old to reply)
4non ym0us
2006-07-17 09:36:04 UTC
Permalink
I don't know if anybody is doing the same thing but I've set up one of
my personal domains smtp/pop3 emails to use Thunderbird/SOCKS/Tor so
that the receipients can't pinpoint my IP.

However, I notice a persistent phenomenon with this setup is that
receiving emails usually works, but sending mail often fails for no
apparent reason except the generic message from Tbird that it either
cannot connect or the smtp server is refusing connections.

It's highly random, I could send one email and it goes through but the
next doesn't, within the space of a minute.

If I did a direct smtp without going through socks/TOR, it will work
fine. Surfing my personal domain using Firefox through privocy/TOR
also works.

I'm guessing that most of the folks running TOR exit servers are
refusing smtp ports so I'm basically on a random hit/miss whenever tor
attempts to create a circuit to send the email. But surely TOR should
realize when trying to create a circuit, it should at least look for
nodes that are willing to carry the pending packet?


Anybody has a better clearer idea what could be causing this problem? Thanks!
Florian Reitmeir
2006-07-17 10:04:57 UTC
Permalink
Hi,

http://tor.eff.org/faq-abuse.html.en
in short Tor is really the wrong tool to send anonymous mails, maybe
mixmaster is want you want.
Post by 4non ym0us
I don't know if anybody is doing the same thing but I've set up one of
my personal domains smtp/pop3 emails to use Thunderbird/SOCKS/Tor so
that the receipients can't pinpoint my IP.
However, I notice a persistent phenomenon with this setup is that
receiving emails usually works, but sending mail often fails for no
apparent reason except the generic message from Tbird that it either
cannot connect or the smtp server is refusing connections.
It's highly random, I could send one email and it goes through but the
next doesn't, within the space of a minute.
If I did a direct smtp without going through socks/TOR, it will work
fine. Surfing my personal domain using Firefox through privocy/TOR
also works.
I'm guessing that most of the folks running TOR exit servers are
refusing smtp ports so I'm basically on a random hit/miss whenever tor
attempts to create a circuit to send the email. But surely TOR should
realize when trying to create a circuit, it should at least look for
nodes that are willing to carry the pending packet?
Anybody has a better clearer idea what could be causing this problem? Thanks!
--
Florian Reitmeir
Matej Kovacic
2006-07-17 10:07:18 UTC
Permalink
Hi,

what about configuring your SMTP/POP3 port to something else?

bye, Matej
4non ym0us
2006-07-17 15:57:01 UTC
Permalink
Post by Matej Kovacic
Hi,
what about configuring your SMTP/POP3 port to something else?
bye, Matej
I don't have control over the SMTP server on the webhost side so
that's not really an option. :(
Michael Holstein
2006-07-17 17:08:22 UTC
Permalink
Post by Matej Kovacic
what about configuring your SMTP/POP3 port to something else?
Sure .. if you can find a MTA that will do that (and of course you could
always set one up, but that'd totally defeat the purpose of trying to
hide the path).

Really, you're better off with tools like Mixmaster. The alternative is
you could (using TOR) setup a Hotmail or Gmail account, and then (also
using TOR) use one of the various Perl modules that offer an interface
to those and send it that way.

Note that both limit the number of messages/day.

~Mike.
4non ym0us
2006-07-17 16:07:42 UTC
Permalink
Post by Florian Reitmeir
Hi,
http://tor.eff.org/faq-abuse.html.en
in short Tor is really the wrong tool to send anonymous mails, maybe
mixmaster is want you want.
I'm aware of this and believe that it's a lot easier to convince my
webhost, if it comes down to it, to not block TOR exit nodes which
many does not appear to be accepting SMTP anyway, compared to if my
IPs are being used for massive spammage.

Furthermore, I've got pretty much a authoritarian/autocratic
government pretending to be democratic here so I'm not taking any
chances of being made an public example of "abetting illegal
commercial spamming" than I already have. The few ISPs are basically
commercial extensions of the government and getting my account banned
from one effectively leaves me with pretty much no choices.
Marco Gruss
2006-07-17 17:20:13 UTC
Permalink
Hi,
Post by 4non ym0us
I'm aware of this and believe that it's a lot easier to convince my
webhost, if it comes down to it, to not block TOR exit nodes which
many does not appear to be accepting SMTP anyway, compared to if my
IPs are being used for massive spammage.
I think this is the main reason why mailing fails so often: Most exit
nodes simply don't allow connecting to port 25. Every time you try
sending a mail and your exit node at that time doesn't allow it, you'll
get the described timeout.

Marco
Roger Dingledine
2006-07-17 17:33:10 UTC
Permalink
Post by Marco Gruss
Post by 4non ym0us
I'm aware of this and believe that it's a lot easier to convince my
webhost, if it comes down to it, to not block TOR exit nodes which
many does not appear to be accepting SMTP anyway, compared to if my
IPs are being used for massive spammage.
I think this is the main reason why mailing fails so often: Most exit
nodes simply don't allow connecting to port 25. Every time you try
sending a mail and your exit node at that time doesn't allow it, you'll
get the described timeout.
No, Tor is smarter than that: your Tor client knows the exit policies
of the Tor servers, and it picks an appropriate exit node.

If I had to pick a reason for your problem, it would be that only 2 of
the 700 currently running Tor nodes allow port 25 to exit, and these
are likely on all sorts of SMTP blacklists.

--Roger
Jay Goodman Tamboli
2006-07-17 18:55:52 UTC
Permalink
Post by Roger Dingledine
Post by Marco Gruss
Post by 4non ym0us
I'm aware of this and believe that it's a lot easier to convince my
webhost, if it comes down to it, to not block TOR exit nodes which
many does not appear to be accepting SMTP anyway, compared to if my
IPs are being used for massive spammage.
I think this is the main reason why mailing fails so often: Most exit
nodes simply don't allow connecting to port 25. Every time you try
sending a mail and your exit node at that time doesn't allow it, you'll
get the described timeout.
No, Tor is smarter than that: your Tor client knows the exit policies
of the Tor servers, and it picks an appropriate exit node.
If I had to pick a reason for your problem, it would be that only 2 of
the 700 currently running Tor nodes allow port 25 to exit, and these
are likely on all sorts of SMTP blacklists.
Is it possible your mail service can use port 587? I don't know how
many exit nodes allow that (nor do I know how to quickly check), but
I'm using 587 with SMTP over SSL, and it seems to work fine. Check my
headers if you don't believe me. :-)

/jgt
--
http://tamboli.cx/
PGP Key ID: 0x7F2AC862B511029F
4non ym0us
2006-07-19 14:46:48 UTC
Permalink
Post by Jay Goodman Tamboli
Is it possible your mail service can use port 587? I don't know how
many exit nodes allow that (nor do I know how to quickly check), but
I'm using 587 with SMTP over SSL, and it seems to work fine. Check my
headers if you don't believe me. :-)
Just tested this and it works (of course Murphy made sure that port 25
was also happily working tonight).

I'll probably have to look into one more thing since I think most of
the time I'm having problems seems to be on my laptop at the office.

Worse come to worst, I guess I will just have to go back to using TOR
with the domain's webmail. Been trying to avoid this since web mail is
typically snail paced and going through TOR means additional latency
plus pointless html traffic for the onion network.

4non ym0us
2006-07-19 14:36:25 UTC
Permalink
Post by Roger Dingledine
No, Tor is smarter than that: your Tor client knows the exit policies
of the Tor servers, and it picks an appropriate exit node.
Ah, that's good to know, I had certainly hoped the developers wasn't
so careless as to overlook something like that.
Post by Roger Dingledine
If I had to pick a reason for your problem, it would be that only 2 of
the 700 currently running Tor nodes allow port 25 to exit, and these
are likely on all sorts of SMTP blacklists.
Hmm, if my webhost does block the TOR port 25 exit node, then it would
make sense they would had blocked both. Which means I should not be
able to send emails at all.
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