When it comes to operating system security in the traditional sense, FreeBSD has a strong track record (to say the least).  Having said that, there are several twenty-first-century exploit mitigation technologies that are woefully absent.  Chief among these, of course, is support for Address Space Layout Randomization (ASLR), which helps to reduce the risk of a whole host of vulnerabilities such as buffer overflow exploits and return-to-libc attacks.  There have also been various and sundry attempts to take on FreeBSD jails over the years, with varying degrees of success.

Though I can and do trust a well-configured FreeBSD system over other FOSS alternatives- for its ground-up, only-what-you-need approaches as much as any other reason- I'm also not about to turn my nose up at attempts to improve the situation.

Enter HardenedBSD, a fork of the FreeBSD code base that ports various PaX enhancements (such as as ASLR and W^X pages), and provides a few FreeBSD-specific improvements for items such as jails and procfs.  It's been called "grsecurity for FreeBSD" on more than one occasion.  The HardenedBSD projects seems ultimately to be interested in merging these protections into "vanilla" FreeBSD once they've matured and been well-tested by the community.

To that end, I decided to try HBSD on a mature and well-established FreeBSD workstation.  That was roughly two months ago now.  While I can say categorically that there are a few parts of HBSD that are "rough around the edges," on the whole it seems to be a very well-maintained and valuable contribution to the *BSD ecosystem.  Here's the synopsis of my conversation process (feel free to skip past the indented parts if you just want the closing summary):

First off, I decided to do an in-place conversion from "vanilla" FreeBSD 11.0-CURRENT to HardenedBSD 11.0-CURRENT.  This process is not documented anywhere, and your own mileage may vary.  Having said that, it went fairly well from my perspective. 
Since I was on ZFS, I began by setting a mountpoint of "none" on the filesystem containing my system source code, creating a new one with a mountpoint of /usr/src, and pulling the HardenedBSD source down to that.  ZFS deduplication left a total disk usage increase of a few megabytes, once all was said and done for the source code transfer.
The next step was to copy over my custom kernel config, merge in the HardenedBSD-specific items (I did enable ptrace protection), then build and boot into the HardenedBSD kernel.  This went precisely as expected, at least at first.  The early boot messages reflected the enabled security protections, and the system came up to multi-user.  Then came the first snag: the "non-hardened" PAM module for Kerberos didn't work, and failed all attempts.  Since I had the console and all vtys marked as insecure, I had to reboot single-user to log in. 
Naturally, this seemed like a good time to build world, as it seemed obvious that there must be a compatibility issue at work.  This proved to be the case, as a normal ZFS snapshot / make buildworld / mergemaster -p / make installworld / mergemaster followed by another reboot had me logging in with Kerberos again.  Miraculously, all of my out-of-tree kernel modules (namely the nvidia driver and pefs) apparently worked fine without being rebuilt, though I did rebuild them anyway for good measure. 
The final conversion step was to rebuild any ports with changed Makefile options, which I figured out quickly with a diff between the official FreeBSD ports tree and that maintained by HardenedBSD.  For the most part, these consisted of adding PIE support into Chromium, Firefox, and a few others.  HardenedBSD does have a binary package repo that works well, but I usually prefer to build from source anyway.  Sucker for punishment, I guess... 
X.org and SLiM worked out of the box, I logged in to MATE just fine, and tried to fire up the recently-rebuilt Firefox.  Nothing happened that I could see.  Here came the first real "gotcha."  HardenedBSD relies heavily on an in-house utility called secadm to control some of its more advanced functionality.  Though some broad configuration can be done with the usual sysctl mechanisms, secadm is used for e.g. exempting certain programs (ahem, Chromium and Firefox, again) from W^X protection. 
For whatever reason, I didn't get secadm with my installworld process.  Turns out that it's a port, including a kernel module and a userland tool.  Once I installed that, I tried to apply the exemptions recommended on the HBSD wiki for Firefox, Chrome, and Java.  Whoops again- the documentation on their wiki was out of date at the time (it's since been fixed) and didn't reflect a syntax change in their secadm tool's configuration file syntax.  I found an updated example here, fired it up, and voila!  I was off and running.

Two months later, and I've barely noticed the difference between HardenedBSD and stock FreeBSD.  As far as I can tell, that's a good thing.  There are a few extra steps needed in some places, however, and a few quirks of which to be aware:

  • Any file that is currently the subject of a secadm rule cannot be deleted or modified.  The rule must be temporarily removed to allow changes to the file.  It makes sense from a security perspective, but this led me to clearing out my secadm rule set when doing portupgrade runs, and then re-installing the rules using the provided rc script afterwards.
  • Care must be taken in jails, and in particular when using any of the non-W^X safe programs like the web browsers or Java in jails.  secadm is jail-aware, and any per-program exemptions from system protections are not carried from the host in to the jail.  These must be activated within the jail by having a secadm config file and enabling the appropriate rc script.
  • Linux binary compatibility works only if some or all of the PaX protections are disabled per-program or per-jail.  I haven't yet been able to find a reliable pattern.  If you have a small number of seldom-used Linux binaries, you'll probably be fine brute-forcing the secadm rules that work for them (as I've done), but if you rely heavily on many Linux binaries or full Linux jails in FreeBSD, you might want to hold off on HardenedBSD for now.
  • PEFS and HardenedBSD don't like eachother at the moment.  Filesystems will mount and key addition works fine, and the filesystem will behave fine for most normal usage, but e.g. attempts to execute scripts (bash, Python, Ruby, you name it) from within a PEFS mountpoint using "./" syntax will often trigger a kernel panic.  You can get around this by explicitly calling the interpreter first, e.g. "bash ./my-script" though that's a tough habit to remember.  Normal binaries work fine though.  I need to delve in to this, and file a patch or at least a PR with the HBSD folks soon (or perhaps the PEFS folks, as the case may be).
That's really it.  Though there are definitely a few small kinks to work out, I think that the HBSD team has done a remarkable job.  For going completely off-the-map on the in-place conversion, I had a remarkably smooth experience, and my own two months without serious problems suggest the HBSD has a bright future ahead.  You can, of course, always download the pre-built versions and go through the normal installation from scratch, but where's the fun in that?