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Outbound SMTP mail EHLO failing

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Nightfox

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Jul 4, 2011, 6:08:40 PM7/4/11
to All
In the past day or so, I've noticed my BBS is now having a problem sending
outbound internet email via SMTP. When I try to send internet email, I see
this in my mail server log window:

!Delivery attempt #1 FAILED (smtp.comcast.net replied with:
"501 EHLO requires valid address"
instead of the expected reply:
"250 ...") for message ...

What might be the issue? I'm guessing that since it worked before, this is
probably an issue with my ISP?

Nightfox

---
� Synchronet � Digital Distortion BBS - digdist.bbsindex.com
--- Synchronet 3.15a-Win32 NewsLink 1.92
* Vertrauen - Riverside County, California - telnet://vert.synchro.net

Dreamer

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Jul 4, 2011, 11:17:55 PM7/4/11
to Nightfox
To: Nightfox
Re: Outbound SMTP mail EHLO failing
By: Nightfox to All on Mon Jul 04 2011 03:08 pm

> !Delivery attempt #1 FAILED (smtp.comcast.net replied with:
> "501 EHLO requires valid address"
> instead of the expected reply:
> "250 ...") for message ...

Looks like your ISP is verifying your domain name against their records in the
EHLO (extended HELO) command. You may have to find another option for mail
delivery. I recommend simply routing through DM's systems -- less headaches.

Incidentally, if you want to complain loudly about it, this behavior violates
RFC 1123:

5.2.5 HELO Command: RFC-821 Section 3.5

The sender-SMTP MUST ensure that the <domain> parameter in a
HELO command is a valid principal host domain name for the
client host. As a result, the receiver-SMTP will not have to
perform MX resolution on this name in order to validate the
HELO parameter.

The HELO receiver MAY verify that the HELO parameter really
corresponds to the IP address of the sender. However, the
receiver MUST NOT refuse to accept a message, even if the
sender's HELO command fails verification.

Fail. :p


---
� Synchronet � Southeast Texas BBS -- setxbbs.synchro.net

Nightfox

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Jul 5, 2011, 10:46:13 AM7/5/11
to Dreamer
To: Dreamer

Re: Outbound SMTP mail EHLO failing
By: Dreamer to Nightfox on Mon Jul 04 2011 22:17:55

> Looks like your ISP is verifying your domain name against their records in t

> EHLO (extended HELO) command. You may have to find another option for mail
> delivery. I recommend simply routing through DM's systems -- less headaches

I've changed it to relay through Vertrauen. I was doing that for a while, when
I was unable to use my ISP for it, but I tended to think of relaying through
Vertrauen as a "last resort".

> receiver MUST NOT refuse to accept a message, even if the
> sender's HELO command fails verification.

> Fail. :p

:P Silly ISP..

Nightfox

---
� Synchronet � Digital Distortion BBS - digdist.bbsindex.com

Dreamer

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Jul 5, 2011, 1:19:49 PM7/5/11
to Nightfox
To: Nightfox

Re: Outbound SMTP mail EHLO failing
By: Nightfox to Dreamer on Tue Jul 05 2011 07:46 am

> I've changed it to relay through Vertrauen. I was doing that for a while,
> when I was unable to use my ISP for it, but I tended to think of relaying
> through Vertrauen as a "last resort".

I think of it as part of the package. LOL... I've had problems trying to
direct send in the past with my emails landing in spam boxes, or servers
blocking me completely based on my IP range. Have yet to have a problem with
the Vert relay.

> > receiver MUST NOT refuse to accept a message, even if the
> > sender's HELO command fails verification.
>
> > Fail. :p
>
> :P Silly ISP..

It really pisses me off when they break a standard like this. They should
accept the message. It's not their job to filter it, that should be up to the
end recipient.

---
� Synchronet � Southeast Texas BBS -- setxbbs.synchro.net

Nightfox

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Jul 5, 2011, 2:17:40 PM7/5/11
to Dreamer
To: Dreamer

Re: Outbound SMTP mail EHLO failing
By: Dreamer to Nightfox on Tue Jul 05 2011 12:19:49

> > > receiver MUST NOT refuse to accept a message, even if the
> > > sender's HELO command fails verification.

> It really pisses me off when they break a standard like this. They should


> accept the message. It's not their job to filter it, that should be up to t

> end recipient.

It's pissing me off too.. And this just started happening. I was relaying
through my ISP until I noticed this a few days ago.

Nightfox

---
� Synchronet � Digital Distortion BBS - digdist.bbsindex.com

mro

unread,
Jul 5, 2011, 11:57:07 PM7/5/11
to Dreamer
To: Dreamer
.,: This is something about Outbound SMTP mail EHLO failing,
Dreamer said it to Nightfox on Tue Jul 05 2011 12:19 pm
--����������������������-����---���������������---���������--��������

> I think of it as part of the package. LOL... I've had problems trying to
> direct send in the past with my emails landing in spam boxes, or servers
> blocking me completely based on my IP range. Have yet to have a problem wit
> the Vert relay.


you're supposed to forward through your isp, not send directly.
IF you are on a residential ip range.

mro

unread,
Jul 5, 2011, 11:55:04 PM7/5/11
to Nightfox
To: Nightfox

.,: This is something about Outbound SMTP mail EHLO failing,
Nightfox said it to All on Mon Jul 04 2011 03:08 pm

--����������������������-����---���������������---���������--��������
> In the past day or so, I've noticed my BBS is now having a problem sending
> outbound internet email via SMTP. When I try to send internet email, I see
> this in my mail server log window:

> !Delivery attempt #1 FAILED (smtp.comcast.net replied with: "501 EHLO
> requires valid address" instead of the expected reply: "250 ...")
> for message ...

> What might be the issue? I'm guessing that since it worked before, this is
> probably an issue with my ISP?


i have this issue sometimes and i'm on roadrunner.

perhaps it's a synchronet issue or it's our provider missing out
on some commands our servers are sending

mro

unread,
Jul 5, 2011, 11:57:39 PM7/5/11
to Nightfox
To: Nightfox
.,: This is something about Outbound SMTP mail EHLO failing,
Nightfox said it to Dreamer on Tue Jul 05 2011 11:17 am

--����������������������-����---���������������---���������--��������

> It's pissing me off too.. And this just started happening. I was relaying


> through my ISP until I noticed this a few days ago.

try shutting off the server [maybe rebooting] and do some more tests.

Dreamer

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Jul 6, 2011, 1:00:25 AM7/6/11
to Nightfox
To: Nightfox

Re: Outbound SMTP mail EHLO failing
By: mro to Nightfox on Tue Jul 05 2011 10:57 pm

> > It's pissing me off too.. And this just started happening. I was
> > relaying through my ISP until I noticed this a few days ago.
>
> try shutting off the server [maybe rebooting] and do some more tests.

Looks like mro is right. I telnetted to comcast's mail server, and was able to
get past the greeting (250).

220 omta17.emeryville.ca.mail.comcast.net comcast ESMTP server ready
ehlo


501 EHLO requires valid address

ehlo setxbbs.synchro.net
250-omta17.emeryville.ca.mail.comcast.net hello [66.25.237.142], pleased to
meet you

Look through your SMTP logs. If your logging isn't set up for recording the
commands you're sending, turn that on. Synchronet *should* be sending your
domain name after 'ehlo', so the mail server knows who it's talking to.

To double check that one of comcast's servers is not misconfigured, from your
own system, telnet to comcast ("telnet smtp.comcast.net 25"), and type "ehlo
digdist.bbsindex.com". You should get the above response. If not, go ahead
and email them; some comcast admin somewhere forked it up.


---
� Synchronet � Southeast Texas BBS -- setxbbs.synchro.net

Dreamer

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Jul 6, 2011, 12:46:31 AM7/6/11
to mro
To: mro

Re: Outbound SMTP mail EHLO failing
By: mro to Dreamer on Tue Jul 05 2011 10:57 pm

> you're supposed to forward through your isp, not send directly.
> IF you are on a residential ip range.

If I was the only one who intended to use the board's email, I would do that.

I just don't like the thought of Roadrunner seeing someone else using my system
to relay email through them. Say I've got five regular dialup users and they
regularly use setxbbs.synchro.net for email. They each send five emails a day.
I typically send about ten. That makes for an average of thirty five emails,
possibly a high of fifty on a busy day, with six distinct from and return
fields.

I'd rather route through Vert until I can afford a commercial package.

mro

unread,
Jul 6, 2011, 3:44:28 AM7/6/11
to Dreamer
To: Dreamer

.,: This is something about Outbound SMTP mail EHLO failing,
Dreamer said it to Nightfox on Wed Jul 06 2011 12:00 am

--����������������������-����---���������������---���������--��������
> Look through your SMTP logs. If your logging isn't set up for recording the
> commands you're sending, turn that on. Synchronet *should* be sending your
> domain name after 'ehlo', so the mail server knows who it's talking to.

i think something just got borked, and it wont stay like that.
i would recommend doing some tests.

i wouldnt advise contacting comcrap about this before reviewing their TOS.
it could be running a server of any sort is not allowed.

mro

unread,
Jul 6, 2011, 3:43:02 AM7/6/11
to Dreamer
To: Dreamer
.,: This is something about Outbound SMTP mail EHLO failing,
Dreamer said it to mro on Tue Jul 05 2011 11:46 pm

--����������������������-����---���������������---���������--��������

> I just don't like the thought of Roadrunner seeing someone else using my sys


> to relay email through them. Say I've got five regular dialup users and the

> regularly use setxbbs.synchro.net for email. They each send five emails a d

> I typically send about ten. That makes for an average of thirty five emails

> possibly a high of fifty on a busy day, with six distinct from and return
> fields.

why do these people have to use your system when they can use hotmail, yahoo,
gmail?

the reason why you should forward your email through your isp is so you dont
get filtered by everything your system would send an email address too.

bbses dont really have to be email providers for their users; it's just
inviting trouble.

and before you forward through vert you should consider if those spam
blacklists he uses will cause problems.

those lists are WAY too restrictive to be trusted.

Sfqpex

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Jul 6, 2011, 7:40:38 AM7/6/11
to Dreamer
To: Dreamer

Re: Outbound SMTP mail EHLO failing
By: Dreamer to mro on Tue Jul 05 2011 23:46:31

> Re: Outbound SMTP mail EHLO failing
> By: mro to Dreamer on Tue Jul 05 2011 10:57 pm
>
> > you're supposed to forward through your isp, not send directly.
> > IF you are on a residential ip range.
>
> If I was the only one who intended to use the board's email, I would do that
>

> I just don't like the thought of Roadrunner seeing someone else using my sys

> to relay email through them. Say I've got five regular dialup users and the

> regularly use setxbbs.synchro.net for email. They each send five emails a d

> I typically send about ten. That makes for an average of thirty five emails

> possibly a high of fifty on a busy day, with six distinct from and return
> fields.
>
> I'd rather route through Vert until I can afford a commercial package.
>
>

I was trying to figure out how to route through VERT, but didn't see anything
on the synch website about this.. Is it part of the Dove-Net setup that I
completely missed here??


---
� Synchronet � Bedrock BBS - bbs.kristyandrick.com - Just online and growing...

Dreamer

unread,
Jul 6, 2011, 9:12:49 AM7/6/11
to mro
To: mro

Re: Outbound SMTP mail EHLO failing
By: mro to Dreamer on Wed Jul 06 2011 02:43 am

> why do these people have to use your system when they can use hotmail,
> yahoo, gmail?

I plan on offering a small freenet for the few who might want to use it. There
are actually a few people out there who don't really use the Internet much
except for email.

> the reason why you should forward your email through your isp is so you
> dont get filtered by everything your system would send an email address
> too.

That's why I stopped using direct mail. Some ISPs won't even accept the email.

> bbses dont really have to be email providers for their users; it's just
> inviting trouble.

You're right, they don't have to be. But, some of us choose to offer that
service. I disagree that it's inviting trouble; it's no more trouble than if
one were using one of the big free mail providers.

> and before you forward through vert you should consider if those spam
> blacklists he uses will cause problems.
>
> those lists are WAY too restrictive to be trusted.

The forward is only for sending email, not receiving. Replies come straight to
my system. I've found I only had to remove one of the blacklists (I forget
which one now). The way I have things set up, I've been using Synchronet's
email exclusively now for over three months with no problems.

As for offering to users, it's a personal choice.


---
� Synchronet � Southeast Texas BBS -- setxbbs.synchro.net

Dreamer

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Jul 6, 2011, 12:26:36 PM7/6/11
to Sfqpex
To: Sfqpex

Re: Outbound SMTP mail EHLO failing
By: Sfqpex to Dreamer on Wed Jul 06 2011 06:40 am

> I was trying to figure out how to route through VERT, but didn't see
> anything on the synch website about this.. Is it part of the Dove-Net
> setup that I completely missed here??

I can't find any official docs or howtos on it, but there's been plenty of
discussion on Dovenet. If you don't have a copy of the messages, log into Vert
and search.

The short answer, though, is to set the relay up using your QWK
username/password for your BBS and point it to vert.synchro.net. There's
another instance of Synchronet running on a Linux system that I believe is
considered to be faster at processing mail; offhand I think its address is
cvs.synchro.net.

I can swear I've seen a doc on this, but I can't find it at the moment. DM
should be around later today or tomorrow, though. :)


---
� Synchronet � Southeast Texas BBS -- setxbbs.synchro.net

mro

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Jul 6, 2011, 12:51:10 PM7/6/11
to Dreamer
To: Dreamer
.,: This is something about Outbound SMTP mail EHLO failing,
Dreamer said it to mro on Wed Jul 06 2011 08:12 am

--����������������������-����---���������������---���������--��������

> You're right, they don't have to be. But, some of us choose to offer that


> service. I disagree that it's inviting trouble; it's no more trouble than i

> one were using one of the big free mail providers.


i mean it is trouble for the provider[YOU]. the only people who would search
for and use someone like yourself would be a spammer. you are a spammer's
dream.

i'm not just hypothesizing, these are things i've seen over the years.

> As for offering to users, it's a personal choice.

make sure it is allowed by your internet service provider.
there have been people who ran synchronet and who have posted on dovenet who
have been shut down by violating their tos and providing email, or having
some user on their system spam usenet using their system.

Dreamer

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Jul 6, 2011, 5:54:26 PM7/6/11
to mro
To: mro

Re: Outbound SMTP mail EHLO failing
By: mro to Dreamer on Wed Jul 06 2011 11:51 am

> i mean it is trouble for the provider[YOU]. the only people who would
> search for and use someone like yourself would be a spammer. you are a
> spammer's dream.

This is why I want to get a commercial connection. And I disagree about the
spammers; there still exist freenets, and some people use those as their
primary accounts.

I am not a spammer's dream. I've locked down my email system so that only
those people I want to allow can send email.

220 setxbbs.synchro.net Synchronet SMTP Server 1.515-Win32 Ready
helo netbook
250 setxbbs.synchro.net
auth plain <redacted>
235 User Authenticated
mail from: blue....@setxbbs.synchro.net
250 OK
rcpt to: perk...@yahoo.com
553 Relaying through this server requires authentication. Please authenticate
before sending.

This is a level 50 user account I keep for testing with the appropriate
restriction to disallow network mail.

Digital Man

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Jul 6, 2011, 11:56:26 PM7/6/11
to Sfqpex
To: Sfqpex

Re: Outbound SMTP mail EHLO failing
By: Sfqpex to Dreamer on Wed Jul 06 2011 06:40 am

> Re: Outbound SMTP mail EHLO failing
> By: Dreamer to mro on Tue Jul 05 2011 23:46:31
>
> > Re: Outbound SMTP mail EHLO failing
> > By: mro to Dreamer on Tue Jul 05 2011 10:57 pm
> >
> > > you're supposed to forward through your isp, not send directly.
> > > IF you are on a residential ip range.
> >
> > If I was the only one who intended to use the board's email, I would do
> > that
> > I just don't like the thought of Roadrunner seeing someone else using my
> > sys to relay email through them. Say I've got five regular dialup users
> > and the regularly use setxbbs.synchro.net for email. They each send
> > five emails a d I typically send about ten. That makes for an average
> > of thirty five emails possibly a high of fifty on a busy day, with six
> > distinct from and return fields.
> >
> > I'd rather route through Vert until I can afford a commercial package.
> >
> >
>
> I was trying to figure out how to route through VERT, but didn't see
> anything on the synch website about this.. Is it part of the Dove-Net
> setup that I completely missed here??

As long as your authenticate with SMTP (e.g. using a user or QWKnet account on
Vert), you can relay mail through it.

digital man

Synchronet "Real Fact" #30:
The Synchronet IRC server (ircd) was written in JS by Randy Sommerfeld (Cyan).

Nightfox

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Jul 7, 2011, 10:18:58 AM7/7/11
to mro
To: mro

Re: Outbound SMTP mail EHLO failing
By: mro to Nightfox on Tue Jul 05 2011 22:57:39

> try shutting off the server [maybe rebooting] and do some more tests.

Thanks for the tip.

Nightfox

---
� Synchronet � Digital Distortion BBS - digdist.bbsindex.com

Nightfox

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Jul 7, 2011, 10:19:26 AM7/7/11
to Dreamer
To: Dreamer

Re: Outbound SMTP mail EHLO failing
By: Dreamer to Nightfox on Wed Jul 06 2011 00:00:25

> > try shutting off the server [maybe rebooting] and do some more tests.

> Looks like mro is right. I telnetted to comcast's mail server, and was able

> get past the greeting (250).

I didn't think of trying that.. I'll try it and see if it works.

Nightfox

---
� Synchronet � Digital Distortion BBS - digdist.bbsindex.com

Sfqpex

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Jul 10, 2011, 10:14:32 AM7/10/11
to
To: Digital Man

Re: Outbound SMTP mail EHLO failing
By: Digital Man to Sfqpex on Wed Jul 06 2011 20:56:26

> >
> > I was trying to figure out how to route through VERT, but didn't see
> > anything on the synch website about this.. Is it part of the Dove-Net
> > setup that I completely missed here??
>
> As long as your authenticate with SMTP (e.g. using a user or QWKnet account

> Vert), you can relay mail through it.
>
> digital man
>
> Synchronet "Real Fact" #30:
> The Synchronet IRC server (ircd) was written in JS by Randy Sommerfeld (Cyan
>

Hi DM,

Thanks! I was trying to figure out where in SCFG I make those settings.. I
see an entry for Internet E-Mail -- Is that correct?

Sorry for the newbie questions..


---
ţ Synchronet ţ Bedrock BBS - bbs.kristyandrick.com - Just online and growing...

Digital Man

unread,
Jul 12, 2011, 9:54:24 PM7/12/11
to Sfqpex
To: Sfqpex

Re: Outbound SMTP mail EHLO failing
By: Sfqpex to Digital Man on Sun Jul 10 2011 09:14 am

> Re: Outbound SMTP mail EHLO failing
> By: Digital Man to Sfqpex on Wed Jul 06 2011 20:56:26
>
> > >
> > > I was trying to figure out how to route through VERT, but didn't see
> > > anything on the synch website about this.. Is it part of the
> > > Dove-Net setup that I completely missed here??
> >
> > As long as your authenticate with SMTP (e.g. using a user or QWKnet
> > account Vert), you can relay mail through it.

> Hi DM,


>
> Thanks! I was trying to figure out where in SCFG I make those settings..
> I see an entry for Internet E-Mail -- Is that correct?

Well, that's where you set your domain/host name, but the mail server settings
go in your ctrl/sbbs.ini file (and can be edited with the
SBBSCTRL:Mail->Configure menu option, if you running Windows). See
http://wiki.synchro.net/faq:tcpip#send_mail for details.

digital man

Synchronet "Real Fact" #3:
Synchronet version 3 is written mostly in C, with some C++, x86 ASM, and Pascal.

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