mutt not sending to hotmail addresses but sendmail will...

[foz_67]

Hi there,

I hope someone might be able to help here.

Using SCO 5.0.6
Sendmail 8.9.3
Mutt 1.2.5.1

Not sure what all you might need for info, but in a nutshell I can send
emails to a test hotmail account through sendmail, but can't send to
any hotmail accounts using Mutt.

I can send to gmail, telus, shaw, etc, but not to Hotmail.

Has anyone had this kind of issue before?

Please indicate what kind of info you might need to help...

Thanks,
Don.

[foz_67]

UPDATE...
I just tried something else...
I can send an email IF NO ATTACHMENT.

This is how I'm sending... (email addresses are fake in the examples)

This does work...
mutt -s "E-mail test" -a attached.txt test...@testdomain.com <
body_of_email.txt

This does NOT work...
mutt -s "E-mail test" -a attached.txt test...@hotmail.com <
body_of_email.txt

This does work... (but no attachement)
mutt -s "E-mail test" test...@hotmail.com < body_of_email.txt

Thanks for your help!

[Keith Thompson]

How exactly does it not work?

--
Keith Thompson (The_Other_Keith) ks...@mib.org <http://www.ghoti.net/~kst>
San Diego Supercomputer Center <*> <http://users.sdsc.edu/~kst>
We must do something. This is something. Therefore, we must do this.

[Jim Tee]

Does mutt fail or does the email just not show up at the hotmail inbox?
If that is the case then maybe it is filtered out as spam. Then you
should ad the address to your contacts list so it will be delivered to
your inbox.

[foz_67]

Hi Keith,
Thanks for responding.
It doesn't work in that the email never reaches the destination if I
have an attached file and it's a Hotmail account.

For example... if I send an email to that same Hotmail account from
Outlook with an attached file it will arrive without issue.

Now my examples above that do work using sendmail might not be that
accurate because sendmail puts the attachement into the body of the
email and not as a true attachment.

If using Mutt and I send an email to any other address I've tried with
an attachment, it does arrive to the respectful address.

Thanks for your input,
Don.

[foz_67]

Hi Jim,

Thanks for your help.

Yes, the email never shows up if I add any attachment when using Mutt.
I don't receive any errors from Mutt when sending, so really, it does
seem that it's being sent.

Thanks for your thoughts on the spam filter. Currently at that hotmail
account all spam just goes to the junk folder. But just in case I
missed something with it I'll double check that and test it out again
tomorrow.

Thanks again,
Don.

[foz_67]

Also Jim,

It won't arrive at any Hotmail account I've sent to so far (4 of them).

Thanks again,
Don.

[foz_67]

Hi Peter,

I'm using Sendmail 8.9.3.

Thanks,
Don.

[Ian Gregory]

On 2006-04-11, foz_67 <foz...@hotmail.com> wrote:
>
> I hope someone might be able to help here.
>
> Using SCO 5.0.6
> Sendmail 8.9.3
> Mutt 1.2.5.1
>
> Not sure what all you might need for info, but in a nutshell I can send
> emails to a test hotmail account through sendmail, but can't send to
> any hotmail accounts using Mutt.

I have a similar problem with mutt and hotmail - similar but different.
Here is my setup:

Debian 3.1
Exim version 3.36 #1 built 08-Apr-2005 20:01:27
Mutt 1.5.9i (2005-03-13)

I was having problems with hotmail users not receiving my email, not
in the junk folder, no bounce, nothing. I eventually spotted a pattern,
which is that I could reply to hotmail users but if I composed a new
message in mutt it always seemed to go astray. I signed up for my own
hotmail account to do some more controlled testing and it seemed to
confirm my hunch. Note that I am not attaching anything to the emails
that are dissapearing.

If I send myself an email from the hotmail account and reply to it
using mutt the reply reaches the hotmail account fine. However, if
I compose a new message in mutt and send it to the hotmail account
(with the same To: and From: headers as the reply which worked) it
vanishes without trace. I am not aware of any problems sending to
the 300 or so non hotmail accounts in my address book.

I have started documenting the phenomenon here:

http://www.zenatode.org.uk/ian/internet/hotmail.html

Ian

--
Ian Gregory
http://www.zenatode.org.uk/ian/

[Ian Gregory]

On 2006-04-26, Peter H. Coffin <hel...@ninehells.com> wrote:

> On 26 Apr 2006 04:51:04 GMT, Ian Gregory wrote:
>
>> If I send myself an email from the hotmail account and reply to it
>> using mutt the reply reaches the hotmail account fine. However, if
>> I compose a new message in mutt and send it to the hotmail account
>> (with the same To: and From: headers as the reply which worked) it
>> vanishes without trace. I am not aware of any problems sending to
>> the 300 or so non hotmail accounts in my address book.
>>

> Try sticking copies of the References: line into entirely new emails
> constructed the same way as the ones that went missing. It's possible
> that Hotmail is just "leveraging" off of that as a side effect spam
> detection of some kind that they just don't tell the customers about for
> fear of spammers learning the trick.

I tried that but had problems. I composed a message and then instead
of hitting "y" to send, I hit "E" to edit headers. I added two headers:

References: <f...@bar.invalid>
X-test: test

I quit the editor and then hit "E" again. The X-test: header was
still there but the References: one was not. It seems like mutt
is refusing to allow me to "spoof" a References: header. Is this
to be expected? Is there a way around it?

Well there is one way round it. I picked a random email sent to
me from somebody else and hit "r" to reply but then changed
the To: header to go to my test hotmail account. I sent that
and it worked.

So hotmail does not seem to care about the form of the References:
and In-Reply-To: headers, but if neither exist then the email
just dissapears into a black hole.

If this is true in general and not because of some peculiarity in
my setup, I would estimate that there must be millions of emails
vanishing every day.

> As for the .gbl TDL mentioned at the webpage, I'd imagine it's either an
> intentional differentiation between internal machines and external
> machines that happens to leak to the external DNS, or it's an
> intentional change to prevent MX load from harvested message IDs being
> tried as email addresses for spam delivery, or possibly both. Message
> IDs do get harvested by dumber parsers. My mail logs are littered with
> them. If they have an invalid TLDs, then those spam attempts will
> completely fail using the normal procedures for delivering mail, which
> contaiminates a spammer's mailing list. And, again, a quick look at a
> mail log will show that spammers NEVER bother to clean a mailing list.

RFC 2111 makes it clear that Message-ID should be globally unique - how
can that be guaranteed if people just invent bogus domains? But quite
apart from that, if Microsoft want to use an invalid domaain they should
use the .invalid TLD as per RFC 2606. If they want to use something that
resolves then they should register a domain for the purpose. What if a
new .gbl TLD is introduced in future and someone registers phx.gbl?
Their DNS servers will be flooded as soon as they come on line.

Grrrrrr

[foz_67]

Hi Ian

Thanks for responding and posting your site.
I've gone over your recent update on your webpage and I'm going to try
out what you were testing tomorrow!!

Thanks again.
Don.