On 29 Jul 2016, at 5:57, Ralph Seichter wrote:

On 29.07.2016 09:29, Roger Goh wrote:

is there any chance that a whitelisted IP address [...] could have
been spoofed?

Yes. Search for "IP address spoofing" in the search engine of your
choice and you will find what you are looking for.


By that standard, we are ruled by a disguised race of alien lizard-people. (Really, Google it...)

Spoofing the IP address used by a running system for TCP sessions is *possible* but it requires very specific complex compromises targeting the network paths between the spoofed system and the system(s) being targeted by the deception. It requires specific points of vulnerability which are relatively easy to avoid. It is not the sort of attack that can be done by any script kiddie with a kit (unlike IP address spoofing as a component of DDoS and reflection/amplification attacks.) This means that to assess your actual risk (or determine the likelihood that spoofing was involved in a specific incident) you need to look at much more than the technical possibility, you need to weigh the value of the attack relative to the difficulty of mounting it. That obviously is out of scope for this or any other public forum, as it has nothing to do with Postfix and requires specific knowledge of your business that should probably not be public.

HOWEVER, in general when someone suggests that a Received header in a piece of email describes an incident of IP spoofing, they are wrong. This is because it is very rare for IP spoofing to be the simplest or most likely explanation. For example, since you have 2 systems involved in a SMTP transaction and the primary records of that are a Received header and system logs, all an attacker needs to do in order to mimic IP spoofing is to compromise one system or the other, preferably the SMTP client. That's likely to be easier for an attacker to execute, harder to detect in progress, and simpler for an attacker to clean up afterwards to prevent tracking. In order to conclude that an incident was the result of IP spoofing one must eliminate the other possibilities such as client compromise, because it's easier to take over most machines than it is to impersonate them while they remain online.

And if one wants to remove the potential for IP spoofing of SMTP between a specific pair of machines across the Internet, this can be done with a simple encrypted tunnel between them: a trivial degenerate VPN with 2 nodes and strictly controlled access on both ends.

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