Sunday 14 December 2014


OpenBSD and FreeBSD are both great OS that I admire and use. OpenBSD is considered more secure since it is its main goal, but FreeBSD can be tweaked to be pretty well hardened as well. Depending on the forums or to who we ask, we will have different opinions. But what are the facts? Which OS is more secure and why?

I am not asking the question about which one is globally better, as "better" has a different meaning depending on the context and the needs (ISP routers, database servers, home gateway, desktop system, storage server or appliance, etc...). On some enterprises doing a major OS upgrade every 6 months or every year is doable, on others, it's not possible at all. Also, it depends if one needs performance for streaming (Netflix), or if security is a top priority for a redundant firewall. Everyone needs is different, and both OS are highly useful.

If we strictly focus on security, how does FreeBSD compare to OpenBSD security-wise? In what follows, we will dig into memory protection, system and network security features, and default "out of the box" security. The purpose is to give unbiased facts, to compare point by point both OS. I am not trying to find the "best" OS and discredit the other, I love and use both :-) Let us try to find out the integrated security features of both OS, the visit continues below!


The security issue most OS are facing are overflows (buffer, heap). When such a vulnerability exists in an OS service or an application, it can be possible for an attacker to exploit it to make a Denial of Service, or remotely executes its code, a payload. We see an endless discovering of such vulnerabilities witch often ends up in remote code execution. It is a very critical issue, and both OpenBSD and FreeBSD have some defenses against it. Some of the following information is extracted from a Theo de Raadt presentation document as well as other sources.


The first problem is that by default, a given program always has its stack at the same address. Therefore, you can find the buffer address and overflow it, with an appropriate exploit. That leads to a very classic buffer overflow, with potential remote code execution (on a network related service for example). The buffer overflow is due to a common programming error, where a bounds check is lacking. For instance filling a 16 bytes buffer with 100 bytes data supplied by an external source (without checking and discarding it). If the supplied data is maliciously constructed, it can inject executable code into the process and take control of it. If the vulnerable process has root/admin rights that's even worse!

The solution implemented into OpenBSD, is to place a variable memory gap before the stack. Consequently, each time a given program runs, its stack will never start at the same address, and thus the buffer has a non fixed address too. This was easily implemented into the kernel, and it renders stack overflows more difficult. It is enabled by default.

I am not aware of a similar random stack gap memory protection on FreeBSD.


Another problem with memory exploits such as buffer overflows, is that the address space has memory that is both writable and executable. Therefore it is possible to write/inject executable code into the vulnerable process stack, and then use the vulnerability to execute that code. If it wasn't possible to execute a writable area, or if it wasn't possible to write to an executable area, exploitation would be much harder.

The solution was implemented into OpenBSD with the W^X policy. The first step to render the stack non executable, is to move away from the stack top page the "signal trempoline" (sigtramp). This move is done at a per-process random address. Now the stack can be rendered non executable. That would seem great, however stopping here would not be enough. Indeed, shared libraries used by the process can still have writable/executable pages. Also, additional objects are executable when they do not require it: Global Offset Table (GOT), Procedure Linkage Table (PLT), c++ constructors (ctors), and c++ destructors (dtors). To fix that, OpenBSD gives GOT and PLT their own non writable page, ctors and dtors move with GOT thus becoming non writable too. At the end, no page is both executable and writable. Another trick is about readonly strings and pointers stored in the .text segment, being executable. They are now moved in the ELF .rodata segment being readonly. Finally, the atexit() function has been modified to not contain writable function pointers anymore. At the end, the overall W^X policy is a beautiful piece of work, and it is enabled by default.

On the FreeBSD side, the non-executable stack is enabled by default for 32bits and 64bits system for ELF, with the sysctl parameters kern.elf32.nxstack=1   and kern.elf64.nxstack=1 . I did not find much information about its implementation, so I guess it just marks the stack as non-executable with the NX bit.

1.3 - ASLR

Exploiting a flaw requires at some point to locate and use a memory address, where a particular piece of code of interest is. ASLR's job is to randomize the position in memory of such area : stack, heap, and libraries. This way, every time a process starts, its libraries won't be loaded at the same address, making the job more difficult for the attacker to predict target adresses. For instance, an exploit such as return-to-libc, which can bypass non-executable stack protection, would be stopped by ASLR as libraries addresses are random.

OpenBSD introduced ASLR and enabled it by default in its system in 2003, and modified it in 2008. It is implemented to randomize shared librairy mapping, base address of mapping, and order of mapping. Each time a process runs, libraries and mapping addresses, and mapping orders, are differents. In 2008, Position Independant Executable (PIE) was added to ASLR. PIE makes the main base program to be randomly loaded as well, as if it was itself a shared librairy. On each run, the main program has a new address.

Another feature used in OpenBSD ASLR is randomized mmap(). This function is a call that maps files or devices into memory. Each time a process makes that call, unless explicitely requiring a fixed address, the result will be a random address, adding yet more memory randomization. A similar feature is random malloc(). This function is used to manually allocate dynamic memory. Tiny malloc() calls are randomly allocated within a special "bucket" page, while larger ones rely on random mmap(). malloc() always randomize, but the addition of guard pages has to be enabled in malloc.conf with the G option. Few malloc() features cannot be enabled by default yet, as some program not well coded are bugging with it. In case it would still not be enough, the free() call delay is also random.

As of December 2014, FreeBSD 10.1-RELEASE has no ASLR available yet. Oliver Pinter started working on ASLR on its side, and Shawn Webb joined him later on to help work on the matter. You can follow their work on GitHub. On March 2014 Shawn Webb has written being hard at work on FreeBSD ASLR implementation. Also, they together have created in 2014 the project HardenedBSD (based off FreeBSD) meant to bring security enhancements to FreeBSD. Shawn Webb highlights that their current ASLR implementation for FreeBSD uses stackgap randomization, which is weak. They are working on true stack randomization to have a stronger ASLR. Also, and it is really worth mentioning, they are actively working on W^X, true stack randomization, and vDSO (virtual Dynamic Shared Object) randomization. All of that work is planned to be upstreamed in FreeBSD.


Another way to defend against buffer overflows is to introduce what is commonly called a "canary". A canary is a random number/flag inserted on the stack at runtime. Afterwards, this canary is checked, and if the value has changed, it means the stack was overwritten and the program is terminated. OpenBSD Stack Protector implementation also does a reordering on the stack of strings, integers, and pointers. It moves strings closer to the canary, and integers and pointers farther.

In FreeBSD, such memory protection mechanism exists and is called Stack Smashing Protection (SSP) or "ProPolice", where a canary (called "guard") is inserted on the stack. SSP exists since FreeBSD 8.0 but only applied to the base system at first, until very recently (November 2014), which means that third party packages finally also benefit from it (i.e Apache, NGINX, Postfix, MySQL, etc...). SSP also reorders local variables and pointers. Apparently ProPolice have to be enabled with the security.bsd.stack_guard_page=1   sysctl (disabled by default). security.bsd.stack_guard_page sysctl description is "Insert stack guard page ahead of the growable segment", which would match ProPolice behavior.

OpenBSD has an additional mechanism called StackGhost only available on Sparc/Sparc64. It is a weaker stack protector but has no overhead. It uses a unique hardware feature of Sparc architecture.


FreeBSD has a "NULL page mapping" protection which is enabled by default, with the sysctl security.bsd.map_at_zero=0 . This prevents a user to call mmap() with a NULL page. I found no direct mention of mapping at 0/NULL on OpenBSD, but Ted Unangst was kind enough to inform me that OpenBSD generally prohibits mmap at NULL by setting VM_MIN_ADDRESS to a value greater than 0 (which is not configurable).

Then FreeBSD has two other memory corruption detections (rather than protection) aimed at debugging, and disabled by default. The first one is called RedZone and is a Heap Smashing detection aimed at debugging the kernel. RedZone is using a static canary value, and is thus less useful than ProPolice. The other one, MemGuard, is a memory allocator used to detect use-after-free exploits. However it is not compatible with the Universal Memory Allocator used in FreeBSD. OpenBSD memory freeing implementation relies on munmap(), which unmaps the entire allocation. Further access to this freed memory leads to a crash.

OpenBSD also provides since OpenBSD 2.4 strlcpy() and strlcat() : "The strlcpy() and strlcat() functions provide a consistent, unambiguous API to help the programmer write more bullet-proof code". These functions can help developpers avoid certain coding errors leading to buffer overflows. FreeBSD introduced these functions in FreeBSD 3.3.

To sum up the memory protections available on both OpenBSD and FreeBSD:
OpenBSD :
-> Random Stack Gap, W^X (GOT, PLT, ctors, dtors, .rodata, atexit), ASLR (PIE, mmap, malloc), Stack Protector, StackGhost, munmap(), strlcpy()/strlcat()

FreeBSD :
-> NX, ProPolice, NULL page mapping, strlcpy()/strlcat()

FreeBSD's memory protections are all covered by OpenBSD system wide with W^X, Stack Protector, and ASLR. While I use and love both OS, I must admit that the comparison hurts.

Besides memory protection, system security relies on other areas such as randomness, encryption, privilege separation, and hardening with jail or securelevel for instance. No single element can provide strong security alone, but stacked together, the security gain can be huge. Below we will explore these essential components, and see how our two OS perform in these various areas. The following is based on this OpenBSD slide, another article, and this Sophos NakedSecurity article.


Randomness is absolutly vital for the overall security of a system. Indeed, many functions and features rely upon it, such as key generation for encryption algorithms. If the random generator is weak, it can generate "random" numbers which are in fact very predictable. That would mean being able to break into a system by guessing the cryptographic keys needed to enter. Weak randomness dangerously lowers security. The problem is not easy to solve as computers are deterministics, and generating truly random numbers requires to use external resources (ethernet packets, heat, keyboard inputs, HDD writes, sounds, etc...).

One source of randomness is the well known /dev/random device. However it cannot be called from everywhere, like from a chroot, and it is sometimes not wise to use it, like to use a random ID for a network packet. Accessing /dev/random from a locked area, certain libraries, or for every packet is not possible. OpenBSD created the arc4random() function to answer these needs and create strong randomness (pseudo-random generator). Basically, a seed exists as a file on the filesystem, at boot time it is used and mixed with clock sources and available interrupts, then passed to the kernel as an ELF segment, and goes trought the ChaCha20 cipher (instead of RC4, since October 2013). Both rc.script and shutdown script create a new seed, and periodic reseeds are done in between (for instance after a certain amount of time has passed). This randomness is then used accross the whole system for ASLR, mmap(), malloc(), SSP, process ID, thread, packet ID, packet sequence number, /dev/random, NAT, port allocation, etc...

arc4random() is used as well by many other OS, including Android, Blackberry, MacOS, NetBSD, and FreeBSD. The OpenBSD slide linked above however blames FreeBSD RPC xid number generation to be based on an old algorithm where the number is not really random at first, and subsequently incremented. There is not much information about that point, even in the Hackfest 2014: "arc4random - randomization for all occasions" video. It would mean FreeBSD does not use arc4random() for that particular xid generation. Also, while OpenBSD's process ID are random by default, it has to be enabled on FreeBSD with the sysctl kern.randompid   and takes as a value a modulus number, the greater the more random (i.e kern.randompid=1000 ). Finally, while OpenBSD and FreeBSD both use a strong random generator that can be relied on, Ted Unangst from OpenBSD, said in September 2014 "arc4random implementations in FreeBSD and NetBSD aren't quite state of the art anymore". I have no details about that point.


Once strong randomness is achieved, we can use it for encryption. On every OS, encryption can be used to encrypt files or communications (SSH, SSL, IPSEC, etc...). Both OpenBSD and FreeBSD are able to do swap encryption, however it is enabled by default only in OpenBSD. To do that on FreeBSD you can follow the security chapter of one of my previous article.

One of the most exciting news from the last months regarding crypto is the birth of LibreSSL, created by OpenBSD (and included in OpenBSD 5.6).

LibreSSL was created to replace the (in)famous OpenSSL crypto and TLS library. OpenSSL has suffered in 2014 a major security bug, the catastrophic Heartbleed. Heartbleed is a vulnerability allowing anyone to remotely read a vulnerable system memory in a non intrusive way, to retrieve secret keys, usernames and passwords. I was able at that time to test a vulnerable system with Metasploit and see with horror the username and password in plaintext at first try... That event motivated OpenBSD team to look into OpenSSL library, and they saw so much non sense (like heartbeat feature only useful for DTLS protocol over UDP, implemented for TLS over TCP) and coding mess, that they decided to fork OpenSSL. More detailed information about why OpenSSL is badly coded on this page.

LibreSSL, while having a cleaner code base and fixing some coding horrors, supports also more ciphers such as Brainpool, Chacha, Poly1305, and ANSSI FRP256v1. There is ports for other OS, but I hope to see it integrated and used by default in FreeBSD in the future, like OpenSSH is.


Often a program needs to do a few privileged operations, while all of its other operations can be made with unprivileged user rights. Even if such program needs admin rights just when starting up, for opening a socket for example, it will then keep it until it ends. That means that all of the operations done while it is running will be with higher privileges than needed, which can be very dangerous. Any attacker successfully exploiting such service will gain admin rights on the system.

Then comes the notion of privilege separation. which is best explained with OpenSSH. One way to separate privileges is to create two processes. The parent one with privileged rights, also called the monitor, and the unprivileged child, also called the slave. The child runs as an unused user, and is chrooted in /var/empty. While the parent receives the first connection request, the key exchange and authentification is delegated to the forked child, which communicates with the parent trough a secure interface. The parent decides if the authentication is sucessful or not and informs the child. Once authenticated, another child is forked wih the authenticating user rights, and handles the new SSH session. This way at the most exposed time, when an attacker may try to authenticate, brute force, or exploit SSH, the child has no rights and is chrooted. Above is the simplified version, technically the parent accepting the connection forks a privileged child handling that particular connection, which itself forks an unprivileged one (the rest stay the same as above). More detail in depth in this paper.

OpenBSD by default uses privileges separation for many programs. I found a list on this 2010 document: sshd, bgpd, ntpd, ospfd, dvrmpd, ospf6d, spamd, relayd, ripd, pflogd, snmpd, hostapd, smtpd, tmux, ypldap, ldpd, syslogd, mopd, bind. Other known programs: Postfix and qmail. I can also see on my router that the following programs have both a root process and an unprivileged child : ntpd, sshd, syslogd, pflogd, named, openvpn, and even tcpdump (which is in addition chrooted). It may have many more programs concerned, that is just my router. OpenVPN client has to be configured to run chrooted in its .ovpn file with 3 lines : user _openvpn, group _openvpn, chroot /var/empty (don't forget to mkdir /var/empty/tmp). Dnscrypt-proxy is an example of a program which chroots itself to its user's (_dnscrypt) home directory and drops root privileges (that's called privilege revocation).

On FreeBSD side, the privilege separation is handled by the recent Capsicum feature. It was experimental and optional in FreeBSD 9, and is now enabled by default since FreeBSD 10.0. Capsicum is a sandbox framework from the University of Cambridge Computer Laboratory, supported/funded by Google and the FreeBSD Foundation. Capsicum allows programs to have capability flags, granting them only needed system calls. A capsicum enabled program will only be able to make system calls its capabilities allow it to. For instance if a developper makes an application to read files, he can build capsicum calls in its application to request only file reading/opening capability. Consequently, if the applications misbehaves, no matter because of a bug or an exploit, it won't be able to open a socket or make outbound network connections, terminate other processes, load kernel modules, etc... The application being sandboxed, its file reading requests will be delegated to a trusted component operating outside the sandbox, ensuring privilege separation. Capsicum is used by FreeBSD to harden OpenSSH built-in privilege separation explained above. Capsicum is used in FreeBSD 10.0 by default on the following programs: tcpdump, auditdistd, hastd, dhclient, kdump, rwhod, ctld, iscsid, and uniq. There is a difference however about tcpdump on FreeBSD, which although using Capsicum, is still running as root. An example on how Capsicum is used for dhclient : "It is no longer possible for the unprivileged process to send UDP packets to arbitrary destinations".

Both OpenBSD and FreeBSD take privilege separation seriously.


When we have strong memory protection in place, true randomness, cryptography, and privilege separation as a core rule, what can we do to harden the system further? Both OS uses a securelevel in which they run, and depending on the level, from -1 to 2 in OpenBSD, and from -1 to 3 in FreeBSD, various security measures are enforced. OpenBSD runs by default at securelevel 1, whereas FreeBSD runs at the unsecure securelevel -1 (disabled) by default. Extract of interesting security measures enforced by securelevel:

Securelevel 1: "Secure Mode"
- /dev/mem and /dev/kmem may not be written to
- raw disk devices of mounted file systems are read-only
- system immutable and append-only file flags may not be removed
- kernel modules may not be loaded or unloaded
- a panic or trap cannot be forced

Securelevel 2: "Highly secure mode"
- all effects of securelevel 1
- raw disk devices are always read-only whether mounted or not
- settimeofday(2) and clock_settime(2) may not set the time backwards or close to overflow
- firewall and NAT rules may not be altered (available on FreeBSD securelevel 3: "Network secure mode")

Securelevels allow the use of chflags, enabling us to put flags on file to make them immutable (cannot be changed, moved, or deleted), append-only, or nodump (won't be backed up by dump utility unless it's a full backup). The immutable chflags is very powerful as even root cannot modify such protected file (system securelevel has to be lowered first by rebooting in single user mode, to modify /etc/sysctl.conf). In Highly secure mode (or Network secure mode in FreeBSD), the system is so locked down than even firewall rules cannot be altered. It can be a powerful tool to harden a system, as well as a pain to administer such restricted server. It should be used wisely. All in all, both OpenBSD and FreeBSD are able to enforce securelevels, although not enabled by default on FreeBSD.

Then, both OS have different security features: systrace for OpenBSD, and MAC and Jails for FreeBSD. Systrace is a tool similar to AppArmor. You can with it define a policy, stay in learning/interactive mode as long as you wish to adapt your systrace policy, and when you are ready, enforce it. A systrace profile will restrict what system calls a program can make, and therefore which actions a program is allowed to do. You can for example allow a process to make DNS requests to localhost but not outside, access /etc/app.conf but not /etc/other.conf, read a file but not killing a process, etc... Generally, making and maintaining program system call enforcement policies is time consuming and tedious. It is moreover more complicated for big/complex programs, that may sudenly exhibit a new behavior not allowed in the policy, or access a new file or path after an update. On the positive side, if well implemented, a systrace enforced program is a lot harder to exploit and abuse.

While on OpenBSD it is possible to combine chroot and systrace to sandbox a program, FreeBSD provides on its side a feature called Jails. A jail is a separate environnement with its own users and processes, its own IP address and hostname. Only the kernel from the host is shared to the jail. For a complete article about FreeBSD and jails you can check my previous article FreeBSD Gateway Hardening : Jails & Intrusion Detection With Snort. Basically, everything installed and running in the jail is separated from the host and cannot access it. By default a jail is very restricted, and programs inside cannot do a simple ping or sniff the network interface traffic. Jails are a convenient way to sandbox a network related program (i.e web server), in a way more secure than a simple chroot, and without to play with AppAmor or Systrace policies (host is unreachable by default). Of course, no matter the program is in jail or not, on FreeBSD or OpenBSD, it still has to be configured and secured correctly (i.e do not load Apache modules you do not need, set appropriate file permissions, apply updates, etc...). Jails are a very convenient feature.

Then there is the FreeBSD Mandatory Access Control (MAC) framework. MAC framework has not much documentation except the FreeBSD handbook, which got me lost at first read. Basically the MAC framework provides security modules, which can be seen as FreeBSD plugins, that extend the security features of the OS or add new ones.

Let's see a concrete example right now. On the base system, without loading any MAC module, you can use the sysctl security.bsd.see_other_uids=0   to prevent users to see processes and network sockets owned by others. It is useful to isolate users globally, and to prevent a webserver for example to be able to return the entire system processes list to an attacker if exploited. However, if for any reason you want to prevent root to see processes and sockets of other users, it's not directly possible. The solution is to use the mac_seeotheruids.ko MAC module, that can be loaded in /boot/loader.conf   with the line mac_seeotheruids_load="YES". Then, new sysctls appear, security.mac.seeotheruids.enabled=1   (by default) which enables the isolation of users except root (same effect as above without MAC). Also, the sysctl security.mac.seeotheruids.suser_privileged=1   (by default) which can be set to 0 to prevent root seeing other processes and sockets. Other sysctls appear that allow you to fine tune exactly what you want, such as exempting certains groups from this policy (which by the way can be the reason to load this MAC module, not necessarily to restrict root).

Other MAC modules exist. The MAC BSD Extended Policy (mac_bsdextended.ko) allows you to create a filesystem firewall, preventing for instance the account uid X to access the object /your/path. The MAC Port Access Control List Policy (ac_portacl.ko) can be used to allow an unprivileged application to bind to a specific privileged port below 1024 (i.e HTTP). Then finally, the MAC framework can be used to put labels on objects, and give clearances on processes/users. This could create a complex policy where top secret information cannot be accessed by objects not having the required clearances. It can ensure, depending on the MAC module used, that a higher clearance object cannot access, or be accessed by, a lower clearance one.

OpenBSD and FreeBSD both have great hardening features which are highly valuable: securelevel and chflags (both), systrace (OpenBSD), Jails and MAC (FreeBSD). Once again, not a single security feature is bullet proof, but used together with what we have talked about above, it can greatly raise the bar for the attacker.



As we have seen in the system security chapter, true randoness is critical to many security areas. Networking is another area which greatly benefits from this randomness pool! Lack of randomness in the network stack has led to many attacks in the past. Even recently (CVE-2014-7284) on 2014 the linux kernel was found on some system to never initialize random seed secret value, used to generate TCP sequence number, IP IDs, and ephemereal ports. Being able to predict some of these numbers, an attacker can hijack a connection, close it, or spoof TCP packets sent to a victim.

On OpenBSD, network randomness is taken seriously. As its randomness is embedded in its pf firewall, and since pf is included on FreeBSD, a FreeBSD system using pf should benefits from the same randomness. FreeBSD's pf version is older than current OpenBSD 5.6 pf version though, more on that later. Network randomness used in pf is pulled from arc4random() we talked before, a reliable randomness source to use in the network stack! To avoid being a predictable network system, randomness is used for: ephemeral source ports, NAT source port, IP IDs, TCP ISN, TCP timestamp, DNS query ID, NTP. NTP protocol by default sends the host localtime to check RTT (Round Trip Time), sending a random value is done instead to avoid information leakage.

Using this randomization and with additional ICMP sequence number verifications, it is possible to block known attacks such as blind connection-reset, blind throughput-reduction (ICMP Source Quench), and blind performance-degrading (ICMP message with "fragmentation needed" + DF bit). This 2005 paper lists OpenBSD as having implemented countermeasures to the 3, while FreeBSD had a 2/3 score, and had an "upcomming" fix for the third attack in 2005 (I hope it's fixed by now, nearly 10 years later). DNS query ID attack is also avoided by the use of pseudo-random DNS query ID and random source port. IPID attack / idle scanning (nmap scan) and TCP fragment injection, are avoided with random IP IDs. NAT deadlock resolution protection requires random source port per destination (ip + port), and TCP ISN modulation. A last issue with extremely busy servers, because of too much TIME_WAIT states, the same {srcip srcport dstip dstport} tuple can be reused, making certain OS to stall affected connections, like XP and FreeBSD (6.x at the time it was said). OpenBSD has applied a patch in 4.4 version. I did not find a patch for FreeBSD by searching "time_wait" in the changelogs of all versions from 6 to 10.1 however, thus it may still be affected.

OpenBSD is clearly proactive in protecting its network stack and improving pf firewall security and reliability. FreeBSD benefits from nearly all of this parameters when using pf, although the security tweaks that has to be done not in pf but in the OS network stack take more time to be implemented into FreeBSD.

3.2 - PF MAGIC

The traffic normalization feature provided by pf (scrub) is a very interesting feature which has broad effects. It is used to handle packet verification, fragments, spoofed traffic, and other malformed packets. It can be used to sanitize a packet before letting it continue its way. It can also be used to enforce a network policy to packets flowing through it. Scrubbing, can:
- enforce a maximum segment size for TCP packets
- enforce a minimum TTL for IP packets
- clear the DF bit of IP packets
- randomize IP ID of packets from hosts having a weak network stack
- statefully normalize TCP [TTL]: no side of a connection is allowed to reduce its TTL
- statefully normalize TCP [Timestamp modulation]: randomize timestamp number
- statefully normalize TCP [Extended PAWS checks]: extend security of TCP sequence number (10->18 bits).

Fragment reassembly is on by default as its advantage (security increase) outweights its downside (memory use). Indeed, when there is no reassembly, only the first fragment contains the necessary headers to be checked against filtering rules, other fragments won't match the rules. No state entries can be created for fragments too. Also, I have seen attacks in the past where the first fragment was forged with the IP headers to "look good", as to fool a firewall, while the fully reconstructed packet could in fact connect to a different port (Overlapping Fragment Attack). It was also possible to crash an OS when it was reassembling the malformed packet (Teardrop Attack). Various fragment attacks explained on this page.

pf can also detect and block spoofed packets with the built-in keyword "antispoof". Instead of creating yourself rules to drop network addresses that cannot be seen on X interface, and create other rules to drop spoofed traffic on Y interface, you can use this simple feature. In one line, pf can block any spoofed packet coming to a given interface. If your LAN network is changed in the future, the ruleset won't need to be updated. It really simplifies the ruleset and spares you doing the job. Likewize, the "urpf-failed" feature can check for you that a packet coming to an interface has an address (i.e the interface passed on (i.e is the correct path to this address (that's a Unicast Reverse Path Forwading).

pf has some other features I won't necessarily detail. Quickly, "synproxy" can protect a server behind the firewall from a SYN flood attack. OS fingerprinting can be added to rules to make more custom rules to allow only certains OS (ex : OpenBSD to the SSH port of the router). You can use "route-to" to route a packet to an interface/path different than the default gateway for instance. You can tag packets to create policy based filtering and create trusted flows, etc...

On both OpenBSD and FreeBSD we can use pf, and therefore have access to all of these features. However, as I mentioned earlier, FreeBSD 10.1 has an old pf version, from OpenBSD 4.5 (2009). Currently, OpenBSD is at version 5.6, which means 11 versions later (5 years). This is very unfortunate as in pf versions above 4.5, between 4.6 and 4.9, performances greatly improve whereas before 4.6 under high load performances collapse. Also, new keywords, features, and syntax was introduced after 4.5, such as the "match" and "divert-to" keywords. A lot of IPv6 fixes and improvements were done, scrub modification, NAT rewrite, and various fixes. Below is a quick sample of few modifications I have choosen to show.

From 4.6 to 5.6, modifications (22 selected modifications, there is a lot more):
4.6 - icmp tracking code rewritten (shotcomings found there)
4.6 - scrub modification
4.6 - "match" keywork
4.7 - NAT rewrite
4.7 - "divert-to" keywork
4.9 - log subsystem rewritten for performance and features
5.0 - Make sure IPv6 packets with routing headers do not create state while dropping them in pf(4).
5.0 - Fixed crash in pf(4) ioctl(2).
5.0 - Fixed potential null dereference in pf(4) ioctl, ahd(4).
5.0 - Added IPv6 ACK prioritization in pf(4).
5.0 - Cleaned up protocol checksums in pf(4), IPv4 and MPLS.
5.0 - Make pf(4) reassemble IPv6 fragments.
5.1 - Improve pf(4) ICMPv6 direction check.
5.1 - pf(4)s IPv6 code evolves further. [...] to make the code more robust.
5.1 - Fix a pf(4) bug where pf_walk_option6() used the outer header in the pd2 case.
5.3 - Lower pf.conf(5) frags limit. Avoids running out of mbuf clusters when dealing with lots of IP fragments.
5.3 - Fixed pf(4) sloppy state tracking missing half the connection in asymmetric setups and ignoring state match in icmp(4) direction checks.
5.4 - Do not reset the pf(4) fragment timeout each time a fragment arrives; drop all fragments if the packet cannot be reassembled within 60 seconds.
5.4 - Before pulling TCP options from the mbuf onto the stack, do an additional length check in pf(4) so overflow cannot happen.
5.5 - Resolved an issue where icmp(4) traffic with pf(4) nat-to failed due to incorrect checksums.
5.5 - Fixed pf(4) icmpid bug (only affected icmp(4) echos via nat, when the nat doesn't change the address).
5.6 - Fixed path MTU discovery with ping6(8) through pf(4) using nat or rdr.

We can see that given all the IPv6 work and fixes, that the current FreeBSD pf version seems broken regarding IPv6. Current OpenBSD pf is bleeding edge, whereas FreeBSD version is a very old version. I know this fact has started debates on the Internet, as Henning Brauer said that current pf was 4 times faster than older versions. FreeBSD has patched its version to be multithreaded, and from what I have read it would be too much work to rework a completely different pf version such as 5.6. You can read this thread Future of pf in FreeBSD ? - does it have one ?. I originally heard about this legitimate interrogation at BSDnow.

There is two opposite stances toward default security. The first considers that it doesn't matter a security feature is enabled by default or not, as long it can be enabled (usually done once when the server is installed, and never touched again). The second one considers that having to enable everything will lead to mistakes, options can be forgotten or wrongly configured. Also, the more security features and options you want to enable, the more an expert you need to be. When it's on by default, you gain a lot of time, you make no mistakes, and you do not need to be an expert. I usually adhere more to the first logic, although I recognize that the second one is completely relevant. Using both OpenBSD and FreeBSD I must admit that secure by default, when it touches so many complex areas we have seen above, should be the gold standard.


Below is a graphical overwiew of what we have seen so far, with MANY CAVEATS thought:
- graphics can be interpreted to make them said opposite things
- I made choices while doing it, but if I did it otherwise I could have made looked better either OS
- I could have added metrics or score, which do not accurately represent a whole OS security
- I added colors to make the reading easier, not to make OS looks good or bad
- having security tools like systrace or MAC is great, but if you don't know how to use them they are useless
- I have chosen to privilege secured by default, but I could have colored in green available security even if disabled by default
- it is only about security, not the whole OS (i.e administration, performance, package install, update/upgrade, hardware support, community, etc...)
- may be you don't care for Sparc64 (and hence for memory protection for this OS)
- graphics are cool and fun, however security being a whole process it cannot be sume up with "green" or "red"
- graphics, by being an overview, are lacking of details (i.e OpenBSD's use-after-free protection with munmap() not present in FreeBSD)

That being said, here it is:

Someone at the back of the room seems to protest, what? What are you saying? .../me dodging flying eggs... Ah ok I understand, no matter it is disabled by default as long as we can enable it. .../me dodging other eggs!...) Ok you don't care for Sparc64, got that. You know building LibreSSL on your system and deal with all linked packages? pf 4.5 is good enough for you? Ok ok, here you go, don't hit me :-)

If we enable all disabled by default protections, either with sysctls (random process ID, SSP), or with manual steps (swap encryption, securelevel, LibreSSL port), if we don't use Sparc nor IPv6, and we disregard bits here and here that are not perfect (RPC xid, arc4random() implementation), the final security could perfectly fits your needs. I am providing both point of view, it's up to you.


OpenBSD developpers constantly have between 6 to 12 of them doing code auditing, instead of writing new code or features. Code auditing allows for finding bugs, or sometimes new class of bugs. This way of working puts a great priority on code quality, that ultimately ends as better security. Indeed, only adding new features and programs and never looking back until a security advisory knocks at your door, is not the best way to make a secure OS.

Most security problems are in fact in the first place simple bugs. When facing a bug it is not always obvious if it can be exploitable and create a vulnerability. In that last case, it can even be harder to gauge the exploitation feasability/probability. What is simple however, is to fix any bug found. This way, if it is later discovered to lead to a security vulnerability, your OS will already be fixed before the problem even exists! Also, when a kind of bug or even a new class of bug is discovered, the code previously audited is audited again looking for this new coding mistake. When not proactively looked for and fixed, bugs that create critical vulnerabilities can exist for years before being discovered:
- WordPress had an XSS flaw for 4 years, which could allow an attacker to execute administrative actions if the website administrator loaded a page containing the rogue comment/code.
- Heartbleed bug has existed for 2 years, and certain people suspect that intelligence agencies were well aware and using it
- POODLE SSLv3 vulnerability has existed for 18 years (since 1996) and can be used to read encrypted communications
- A Windows vulnerability remotely exploitable existed for 19 years and could be used to take over any Windows computer
- The LZO compression algorithm had an integer overflow for 20 years. It is used on many software such as OpenVPN for instance. This flaw may lead to remote code excution under certain conditions.
- Another OpenSSL flaw (CVE-2014-0224) discovered in 2014 existed for 16 years, and could be used to read TLS encrypted communications.
- Shellshock bug existed for 25 years and can be used in many different systems and programs, such as webservers. Even OpenVPN was affected by it.

The above examples show that currently, in any OS, bugs which are exploitable exist. If they are left untouched, they won't magically fix themselves, and will eventually become critical vulnerabilities allowing remote exploitation for 20 years or more! As you may have already noticed, that's not because we do not publicily know a vulnerability, that it has not been known and secretely used by others.

Proactively and aggressively auditing its source code for bugs is a very smart way to dramatically increase security, and is one of OpenBSD's strongpoint being part of the "Secure by default" philosophy.

If we consider memory protection only, OpenBSD is the master in its area (Random Stack Gap, W^X (GOT, PLT, ctors, dtors, .rodata, atexit()), ASLR (PIE, mmap(), malloc()), Stack Protector, StackGhost, strlcpy()/strlcat()), and FreeBSD is severely lagging behind. I hope projects such as HardenedBSD will bring ASLR and more to FreeBSD as soon as possible. Memory exploitation is probably the most common remote exploitation technique, it is not a subject to be trifled with.

Then regarding system hardening, both OpenBSD and FreeBSD are interesting in this regard, in the way they provide different tools to do it. Both can make use of securelevel and chflags, make use of strong randomness, and cryptography. OpenBSD is more privilege separation by default + systrace, while FreeBSD provides also privilege separation with Capsicum, and adds the MAC framework and the famous and very useful jails. The pf firewall is amazing, and I hope FreeBSD will follow more regularily OpenBSD pf versions instead of staying 5 years behind.

With all of that said, which OS is the most secure? Which one to choose? These are not easy questions. Indeed, if we focus only on memory protection, OpenBSD seems to be the way to go. However, if you like or need jails, you won't have any on OpenBSD (although you can use systrace instead, which is not the same thing). At the opposite, you could say that you are aware of the weaker memory protection on FreeBSD, but that you will use jails to isolate your network service. Then we can wonder what would be the best between 1) a system where memory exploitation is very hard and has less chances of success (very low probability of host compromise), and 2) a system where memory exploitation is more probable but the host out of reach because the exploitable service is jailed. That alone will highly vary depending on the software installed and associated risks (a single Postfix VS Apache + MySQL + PHPMyAdmin + Drupal, or a webserver VS a router). Another point of view, is if your webserver is compromised, with all client data, it does not matter if the host will be compromised or not, it's already lost (in that case you may prioritize memory protection with OpenBSD). If you add up other parameters such as ease of administration, LTS versions and support, team work (everyone should know/learn the new system in your team), the "best" OS will be highly individual!

Security is one important parameter, especially nowadays where the Internet is more like an unmerciful war zone than anything else. Vulnerabilities with far reaching consequences hit us many times per year, and everyone is hacking everyone (countries and states included). However, you should understand the OS you choose, and keep it simple. Simplicity is one key to security, and is one area where OpenBSD shines with its secure by default design. However it could be argued that making a jail is easier and stronger than creating and maintaining a systrace policy, and if you perfectly understand jails but not sure about systrace, choose FreeBSD. There is many arguments to prove that both OS are the best! (in no particular order and not necessarily about security: ZFS, SSD, memory protection, jails, pf, journaled-softupdates filesystem, systrace, capsicum, MAC, etc...).

In the end both OpenBSD and FreeBSD have their strongpoints and disadvantages. I really wish both will continue to improve and eventually borrow from each other the best ideas. Projects like LibreSSL or HardenedBSD need our support to improve, don't hesitate to help if you have the possibility.

I wish you a more secure and peaceful 2015 (soon) year! Thank you for reading :-)

updated December 16 2014: FreeBSD SSP, OpenBSD malloc/NULL, random free(), HardenedBSD additional information, default/tweaked graphics



  1. The 'G' option for OpenBSD's malloc(3) only adds guard pages. It returns randomized allocations by default.

    1. The article was updated to fix some points, including this one.


  2. Could it be possible another comparison between FreeBDS, OpenBSD and Linux ?
    Congrats for the blog.

    1. "Linux" is available as many different distributions, they do not ship with the same features enabled (Apparmor or SELinux for instance). I would have to pick one, which would not necessarily be a simple step. Or choose more than one, which would require a good amount of time. So not for now, but who knows... I never know in advance what will be my next subjects :-)


    2. This was a very nice comparison and I've learned a lot from it. I would definitely like to see one comparing them against the latest Linux kernel and core apps with and without AppArmor, GrSecurity, and SELinux. I know it would be a lot of work, but I hope someone will do it someday. Thanks a lot for all your hard work!

    3. A Debian vs. Ubuntu vs. Openbsd comparison would be great!

    4. +1 for including comparision with Linux. :-)

    5. I'd also like to see a comparison with Linux. Ideally, a network and security oriented distribution should be taken for that, and a good candidate would be Alpine Linux, since this one emphasizes these two aspects. I wonder, if OpenWrt, being a distro targeting routers, would offer similar functionality but sort of doubt it. So, I'd definitely like to see Alpine Linux in the mix, since it appears to be uniquely lean while still being complete with out-of-the-box PaX, PIE, LXC and Xen support and an in-memory operation mode.

  3. Great article. I liked your war like conclusion. I was interested to read that freebsd does contain many of the same protections as openBSD but are disabled. (I didn't actually think it contained as many). Thanks

  4. Guillaume Kaddouch: You could test "enterprise" Linux like CentOS (basically RHEL), and the most popular one, Ubuntu, I guess.

  5. Regarding a comparison agains Linux, Alpine Linux is one of the only few real security oriented Linux distributions worth comparing to OpenBSD:

  6. Very informative article. I did not realize how far behind FreeBSD's pf was. I'm curious how much better pfSense and the BSD router project do in that area.

  7. Hi, IIRC systrace is buggy, cf. systrace(1),

    1. Hello,

      Systrace alone is indeed not secure enough, it is mentioned in its man page at the end. However, combined with privileges separation/revocation, and chroot (which is not secure by itself too), then this 3-combo adds some hardening compared to a process running with no protection at all. I find it useful used in addition to other security measures, it should not be solely relied on.


  8. What about privilege escalation flaws in FreeBSD?

    1. Privilege escalations flaws can potentially exist in both FreeBSD and OpenBSD, both have at least one reference that can be found by doing a quick search (FreeBSD mmap & sysret, OpenBSD vga). However FreeBSD seems to have been hit more by this kind of vulnerability than OpenBSD, still from a quick search. That is definitely something I will look into.


  9. curious why you haven't locked down ssh to uncomment protocol 2. Is there a reason for this? Would doing this cause more damage than good?

  10. ^^^ wrong page sorry.

  11. Dude, what about compare OpenBSD and NetBSD ?

  12. Same issue on FreeBSD: Privilege Escalation flaws.

  13. The list is alarming but does show the path FreeBSD has been taking over the years has been the wrong one if your focus is a secure internet server. I would say the 2 most alarming issues is the lack of ASLR on the current release of FreeBSD and the now very old PF that is distributed with the OS. From what I seen on the mailing list the issue with PF is a combination of noone wanting to do the task without payment and the fact the FreeBSD version of PF was forked with SMP support which meant backporting revisions from openbsd became harder to do. It does appear there is a lack of manpower for development on FreeBSD, and they are prioritizing desktop features over keeping up with security. Which is sadly why I have migrated 100s of servers in the last 5 years from FreeBSD to linux. Most of my remaining FreeBSD servers are testing and personal hobby machines.

    I feel security features need to always have a higher priority than other features on FreeBSD development and they should always be backported to the oldest supported branch when possible, as when new security code does ever get added, its usually on CURRENT only meaning its years away from those who follow mature branches.

    1. Agree with Chrcoluk.. not only, but an adamant stay of old A.end binaries in FreeBSD, and perhaps all BSD's .. like ELF Cache binaries.. surprisingly hard to get source or any decent info on how they interact with >2.6kernel its a bit scary when u hear CentOS 7.2 (ok thats a fork of RHEL) suffers in datagram mode on IB.. WHY ? What about other i/O ?

  14. Serious Writing, good that You did wonder in the end real life scenario about boxes with different access .

  15. Guillaume has that producer spirit making more sense than the gameplay itself. Look at it this way: More an authority on human Psychology than programming i like to think of C as a ball of string that unravels as programmers toss it around like cats, then some magic, client interpreted Ruby out of the box.. Python.. always had Perl & TCL (sandbox took on VM of today). Now PHP rules the reusable object roost, by speedups over resource management in frameworks like Zend, yet the interpreter is written in C.. that ball of string) One reason not to learn C, are nightmare pointers that allow external addressing to R/W pages, bounds checking / type variable declarations.. Infinitely implemented in so many specific environments, that fixes cannot be shared without rewriting code, as example for SQLers.

    Ok whats the point (i hear u question) that in the quest for speed (permissive coding) the entire network becomes faulty. ITs not even possible to open a socket without hazard, (containers and VM's go a distance there, yet still cant determine if a handler is passing segmented worms) Congratulations, in the rush for market dominance, u forgot the 2 digit year, that cost the planet trillions of dollars (more than the entire computing effort, in one bubble). Is that smart commerce? its absolutely Stupid commerce, just like compiled rubbish (alright, C has produced RTOS's that block preemption) but where do we go from here.. In a nutshell, a change of paradigm is needed at the CPU level, such as is happening with HMC, the only serious adventure into supercomputing is the Pico SB-801 (& its modular siblings) , even tho Xilinx KU115 is a beast u're not going to find 4 of these bridging one HMC, thus Altera quad-bridge is an exciting re-programmable fabric on an available PCIe board level compiler Lab.
    Dump that register based Von Neumann architecture (apart from embedded SoC where of course playtime with C , continues.. i vote the PIC32 Harvard as the most cost effective controller, nothing wrong using multicore ARM+ GPU ($18 Orange Linux) for video related IoT .. where legacy code prevails. Why take buggy runtime / OS 's .. Any crew members?

  16. "..Capsicum allows programs to have capability flags, granting them only needed system calls. A capsicum enabled program will only be able to make system calls its capabilities allow it to. For instance if a developer makes an application to read files, he can build capsicum calls in its application to request only file reading/opening capability" ABOUT TIME.. what took kernel writer so long

    Why use an OS without this in the first place? i kno, falling over each other 1st 2market with front panel features hidden by behind-scenes crapola SysCalls

    THIS needs to happen at Layer 2,3,4 not @ App layer.. as it is currently (except for magical SysCalls to address hardware - what layer is that App to App or App to board firmware) speaking of which : packet sniffer interacts with ARP table is this effectively wire talking to layer 2 thru compiled object code that remains vulnerable to insertion ? No matter what u do, any open socket is a hole.

    Is there an equiv to W^X (an overdue security fitted to OpenBSD) for sockets.. May i ask why W^X is said to be fitted only to OpenBSD ? IS it possible to compile into FreeBSD (not that anythings wrong with OpenBSD) or Alpine Linux.

    Guillaume sums it up nicely when it comes to choice : " highly vary depending on the software installed and associated risks (a single Postfix VS Apache + MySQL + PHPMyAdmin + Drupal, or a webserver VS a router). Another point of view, is if your webserver is compromised, with all client data, it does not matter if the host will be compromised or not, it's already lost (in that case you may prioritize memory protection with OpenBSD) "

    .. there are those who try to secure promiscuous PHP with OpenBSD !!!

    YEs please, in a DRAM held array database.. Could anyone point to an install proceedure of AeroSpike (via Apache2) on OpenBSD .. does this work in periodic key exchange for remote clients.. looks interesting, tho dont need the buggy backward compatibility nodule..

    Even tho this is not slash forum.. it does illustrate dilemma facing all, juggling fireballs, guarantee to get burnt. Leave this to the hackers.. Anyone ready to write a new kernel that does not compile to a Von Neumann architecture