Schneier asserts that the modern situation is like feudalism. There's a bit of wild west situation in which various groups can cyberattack others and then hide. Powerful entities like Google and the U.S. government have the capacity to defend themeselves against cyberattacks, and even to attack, but most individuals do not; except for the small percentage of technologically sophisticated individuals, similar perhaps to the warrior classes of old. The ordinary individuals, like peasants, are stuck with the security configurations given to them by the feudal lords. The lords usually act in their own interests, rather than for the interests of the peasants.

However, i opine that there are huge differences that make the feudal metaphor ill-fitting. Quoting Wikipedia, "In its classic definition, by François-Louis Ganshof (1944), feudalism describes a set of reciprocal legal and military obligations among the warrior nobility, revolving around the three key concepts of lords, vassals and fiefs....A lord was in broad terms a noble who held land, a vassal was a person who was granted possession of the land by the lord, and the land was known as a fief....the lord and vassal entered into a contract in which the vassal promised to fight for the lord at his command, whilst the lord agreed to protect the vassal from external forces....Since at least the 1960s, when Marc Bloch's Feudal Society (1939) was first translated into English in 1961, many medieval historians have included a broader social aspect that includes not only the nobility but all three estates of the realm, adding the peasantry bonds of manorialism and the estates of the Church; this is sometimes referred to as "feudal society" since it encompasses all members of society into the feudal system.".

The present-day cybersecurity situation involves none of:
(1) peasants who to pay feudal dues
(2) a subset of peasants (call them serfs) who were not permitted to migrate
(3) the Church estates
(4) vassals and peasants to which the lords provide land and protection
(5) vassalage in which the vassal promises to provide military service

The first four are debatable. One might say that one's loss of privacy on facebook is like a feudal due.

Although people are certainly not prohibited from migrating between facebook, gmail, macOS and their competitors, the high costs of migration from lock-in and network effects may be thought of as a "soft serfdom" if not an absolute one.

One might argue that the construct of feudalism is still useful without the role of the Church.

Internet security differs from physical overland security in the feudal era in that a distant invading army need not conquer or ally with your neighbors in order to be able to reach you; cybercriminals can attack you from anywhere in the world. This has implications for the relevancy of a nearby 'lord' who gives you land; however one could still argue that the 'land' being given is something like a software configuration, and to the extent that yours is vulnerable, so are others running similar configurations, so there is in fact some way in which it is somewhat more efficient for the lord to protect 'his' land than for you to contract protection from some other powerful entity on the other side of the globe.

However the last point, vassalage involving military service, is both absolutely central to feudalism and entirely lacking in the present-day cybersecurity situation. Nowdays we exchange money, not service, for protection, and while this arrangement became common in later feudalism, i opine that it is because that was not workable at the beginning that feudalism even arose.

Still, it does seem that the existence of an elite 'warrior class' of cybersecurity warriors is coming to pass: people with both skills that require extensive training, and artifacts which are relatively expensive, and whose skills and artifacts would allow even one of them to decisively defeat large numbers of untrained, poorly equipped non-warriors. The existence of a warrior class was one of the primary reasons that the system of feudalism arose. So perhaps we'll see the emergence of a feudal cybersecurity system sometime in the future, one in which individual cybersecurity experts, and organizations who can employ them, subordinate themselves to greater 'lords' by pledging military service, in exchange for protection and 'land', meaning software platforms and 'network real estate' (e.g. things like a facebook page).

But there are reasons to doubt that. First, i think feudalism arose during a time of a breakdown of trade and declining populations; in such a situation a lord needs to demand military service directly, rather than taxes with which to buy mercenaries, because of high transaction costs. This is not the case today; it is easier for facebook to collect money from business activities and spend some of that on employing cybersecurity professionals, rather than to grant lavish privileges to those of its users who are cybersecurity experts in exchange for their labor.

Second, today many governments might choose to prosecute cybersecurity vigilantes within their borders, making non-state 'armies' of 'cybersecurity warriors' ineffective.

In summary, what Schneier is talking about is a situation where a variety of large organizations have a lot of power. Imo feudalism means something more specific.