[BlueOnyx:21687] Re: mailserver; possible security issue?

Rickard Osser rickard.osser at bluapp.com
Thu Jan 25 09:29:58 -05 2018


Hi Brian,
you don't need to log in to an smtp server on port 25 to send to a
local address. The server thinks you're a server and will receive mails
for the domains and users it handles.Also remember, there is really no
checking on mails at all if the mail-addresses are valid. SPF can help
because that will tell the server you're not on a mail-server but if
you log in to the mail-server first and then do a telnet to localhost
on port 25 it will let you through anyway.
I use this all the time to test mail-server setups.
Best regards,
Rickard

On Thu, 2018-01-25 at 14:21 +0000, Fungal Style wrote:
> Dirk,
> 
> Good to see I am not the only one thinking SPF.
> 
> I note that your test, if I read it right, you are logging in via
> telnet as if you were a mail client, you are authenticating to start
> with.
> 
> So you are saying, as an example….
> 
> The fake user is logging in as user at company.com and then saying the
> sender email address is ceo at company.com ? 
> 
> Also you are saying is you have selected to enable “Enable SMTP Auth”
> in the basic tab of “Email”? If so my understanding would be the user
> would need to authenticate in order to be able to send an email which
> they could say have an email client to log in with the credentials
> for the username of (to use the above example):
> user
> 
> Entering the password etc, but configure the email client to say the
> email is from ceo at company.com and not user at company.com (which was
> used to authenticate for sending email), is this what you mean?
> 
> The question would be then if the above is true then as to if the
> email originated from your (in this case, your customer’s) mail
> server, and if so they may have a compromised email account as you
> needed to log in to send email. 
> 
> Hope that makes as much sense as I think it does as it is nearly
> 1:#0am here… ☺
> 
> Regards
> Brian
> 
> 
> On 26/1/18, 1:06 am, "Blueonyx on behalf of Ken Hohhof" <blueonyx-bou
> nces at mail.blueonyx.it on behalf of khohhof at kwom.com> wrote:
> 
>     Dirk, I am not understanding the issue.  Mailservers will
> generally accept messages from anyone for a local mailbox, that is
> their purpose.
>     
>     Is the issue that the mailserver is accepting external mail from
> a sender address at a domain local to the mailserver?  Maybe you are
> wanting something like SPF to specify the official mailserver for
> that domain and force all senders to authenticate and relay via the
> official mailserver?
>     
>     Or is the issue that the CEO was fired and his/her email address
> deleted, yet the mailserver accepted messages from a sender address
> at a local domain that it should have known was an invalid user at
> that domain?  If I handle mail for a domain, and I receive a message
> purporting to be from a user at that domain, yet there is no such
> user (or alias) at that domain, maybe the SMTP session should fail as
> soon as I receive the sender data.
>     
>     
>     -----Original Message-----
>     From: Blueonyx [mailto:blueonyx-bounces at mail.blueonyx.it] On
> Behalf Of Dirk Estenfeld
>     Sent: Thursday, January 25, 2018 7:19 AM
>     To: BlueOnyx General Mailing List <blueonyx at mail.blueonyx.it>
>     Subject: [BlueOnyx:21683] Re: mailserver; possible security
> issue?
>     
>     Hello Brian,
>     
>     thank you for your email.
>     Yes, I am aware of this. But in this case some of your
> suggestions are not applicable.
>     For example for an official mailserver it makes no sense to limit
> the ip address for port 25.
>     Yes smtp_auth is enabled at the server of course. But you can
> try. It is not working if you use an email address which is existing
> at the server and the recipient address also.
>     
>     I did also try with an exchange server and this was working. Also
> with a sendmail at freebsd. So it seems to be a more  or less general
> "feature" which in my opinion is a security issue in our days.
>     
>     Best regards
>     Dirk
>     
>     
>     ---
>     
>     blackpoint GmbH – Friedberger Straße 106b – 61118 Bad Vilbel
>     
>     Tel.: +49 6101 65788 20
>     Fax: +49 6101 65788 99
>     eMail: dirk.estenfeld at blackpoint.de
>     
>     Vertretungsberechtigt Dirk Estenfeld und Mario Di Rienzo HRB
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>     
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>     
>     
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>     
>     
>     -----Ursprüngliche Nachricht-----
>     Von: Blueonyx [mailto:blueonyx-bounces at mail.blueonyx.it] Im
> Auftrag von Fungal Style
>     Gesendet: Donnerstag, 25. Januar 2018 13:55
>     An: BlueOnyx General Mailing List <blueonyx at mail.blueonyx.it>
>     Betreff: [BlueOnyx:21682] Re: mailserver; possible security
> issue?
>     
>     Hi Dirk,
>     
>     Well, there are often a few things that can be done, although
> normally you need to also consider email is one of the (if not the)
> most insecure methods of communication.
>     
>     Simple things which some you may have enabled already include:
>     - Limiting the IP ranges that can send email (of course can be
> spoofed, but it requires more work from the scammer side)
>     - Authenticated sending (to ensure they do not send via your
> server, if they do then look for the account being exploited)
>     - SPF records can help a little too I believe (have nto played
> too much with them)
>     
>     
>     Note: I am no expert myself but the above should get you pointed
> in the right direction to start with.
>     
>     I am sure there are other ways to harden the security like with
> RBLs, SPAM filetering such as SPAM ASSASIN, etc. I suppose some geo
> blocking may also help, which would go more hand in hand with the
> initial comment on limiting the IP ranges.
>     
>     As always, staff training on cyber threats in invaluable.
>     
>     Hope this helps for the future.
>     
>     I suspect someone with more knowledge will reply also soon
> enough, but thought this may provide a little light reading to start
> with.
>     
>     Regards
>     Brian
>     
>     
>     On 25/1/18, 11:07 pm, "Blueonyx on behalf of Dirk Estenfeld" <blu
> eonyx-bounces at mail.blueonyx.it on behalf of dirk.estenfeld at blackpoint
> .de> wrote:
>     
>         Hello,
>         
>         we have one customer who was victim of a CEO fraud.
>         Some of his employees got a message from the email address of
> the CEO with the order to send xx money to a specific bank account.
> He did :(
>         
>         Now we found out that it is possible to send email with
> sendmail at centos/blueonyx (also other distributions) from an
> existing email address to an existing email address.
>         
>         Example:
>         telnet 208.77.xx.xx 25
>         Trying 208.77.xx.xx...
>         Connected to 208.77.xx.xx
>         Escape character is '^]'.
>         220 sol ESMTP Sendmail Ready; Thu, 25 Jan 2018 06:37:59 -0500
>         EHLO blackpoint.de
>         250-sol.xxx Hello ns3.xxx [xx.xx.xx.xx], pleased to meet you
>         250-ENHANCEDSTATUSCODES
>         250-PIPELINING
>         250-8BITMIME
>         250-SIZE
>         250-DSN
>         250-ETRN
>         250-AUTH LOGIN PLAIN
>         250-STARTTLS
>         250-DELIVERBY
>         250 HELP
>         MAIL FROM:mstxxx at solxxx.net
>         250 2.1.0 mstxxx at solxxx.net... Sender ok
>         RCPT TO: mstxxx at solxxx.net
>         451 4.7.1 Greylisting in action, please come back later
>         RCPT TO: mstxxx at solxxx.net
>         250 2.1.5 mstxxx at solxxx.net... Recipient ok
>         DATA
>         354 Enter mail, end with "." on a line by itself
>         Some content for example send money to yx
>         .
>         250 2.0.0 w0PBbxN1026335 Message accepted for delivery
>         QUIT
>         221 2.0.0 sol.xxx closing connection
>         Connection closed by foreign host.
>         
>         Unfortunately it is not only possible from the same to the
> same user. It is also possible from an (at the server existing) email
> address to an (at the server existing) email address.
>         
>         Does someone else did see something similar.
>         In my opinion in days with CEO fraud it is a security issue.
>         Do someone know how to change settings in sendmail to prevent
> this behaviour?
>         
>         Best regards,
>         Dirk Estenfeld
>         
>         
>         ---
>         
>         blackpoint GmbH - Friedberger Straße 106b - 61118 Bad Vilbel
>         
>         
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Rickard Osser
CTO
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125 44 Älvsjö
Sweden

Web: http://www.bluapp.com
Mail: rickard.osser at bluapp.com
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