The first version of LibreSSL portable, 2.0.0, was released a few days ago (followed soon after by 2.0.1). Despite the 2.0.x version numbers, these are only preview releases and shouldn't be used in production yet, but have been released to solicit testing and feedback. After testing and examining the codebase, my feedback is that the LibreSSL PRNG is not robust on Linux and is less safe than the OpenSSL PRNG that it replaced.

Consider a test program, fork_rand. When linked with OpenSSL, two different calls to RAND_bytes return different data, as expected:

$ cc -o fork_rand fork_rand.c -lcrypto $ ./fork_rand Grandparent (PID = 2735) random bytes = f05a5e107f5ec880adaeead26cfff164e778bab8e5a44bdf521e1445a5758595 Grandchild (PID = 2735) random bytes = 03688e9834f1c020765c8c5ed2e7a50cdd324648ca36652523d1d71ec06199de

When the same program is linked with LibreSSL, two different calls to RAND_bytes return the same data, which is a catastrophic failure of the PRNG:

$ cc -o fork_rand fork_rand.c libressl-2.0.1/crypto/.libs/libcrypto.a -lrt $ ./fork_rand Grandparent (PID = 2728) random bytes = f5093dc49bc9527d6d8c3864be364368780ae1ed190ca0798bf2d39ced29b88c Grandchild (PID = 2728) random bytes = f5093dc49bc9527d6d8c3864be364368780ae1ed190ca0798bf2d39ced29b88c

The problem is that LibreSSL provides no way to safely use the PRNG after a fork. Forking and PRNGs are a thorny issue - since fork() creates a nearly-identical clone of the parent process, a PRNG will generate identical output in the parent and child processes unless it is reseeded. LibreSSL attempts to detect when a fork occurs by checking the PID (see line 122). If it differs from the last PID seen by the PRNG, it knows that a fork has occurred and automatically reseeds.

This works most of the time. Unfortunately, PIDs are typically only 16 bits long and thus wrap around fairly often. And while a process can never have the same PID as its parent, a process can have the same PID as its grandparent. So a program that forks from a fork risks generating the same random data as the grandparent process. This is what happens in the fork_rand program, which repeatedly forks from a fork until it gets the same PID as the grandparent.

OpenSSL faces the same issue. It too attempts to be fork-safe, by mixing the PID into the PRNG's output, which works as long as PIDs don't wrap around. The difference is that OpenSSL provides a way to explicitly reseed the PRNG by calling RAND_poll . LibreSSL, unfortunately, has turned RAND_poll into a no-op (lines 77-81). fork_rand calls RAND_poll after forking, as do all my OpenSSL-using programs in production, which is why fork_rand is safe under OpenSSL but not LibreSSL.

You may think that fork_rand is a contrived example or that it's unlikely in practice for a process to end up with the same PID as its grandparent. You may be right, but for security-critical code this is not a strong enough guarantee. Attackers often find extremely creative ways to manufacture scenarios favorable for attacks, even when those scenarios are unlikely to occur under normal circumstances.

Bad chroot interaction A separate but related problem is that LibreSSL provides no good way to use the PRNG from a process running inside a chroot jail. Under Linux, the PRNG is seeded by reading from /dev/urandom upon the first use of RAND_bytes . Unfortunately, /dev/urandom usually doesn't exist inside chroot jails. If LibreSSL fails to read entropy from /dev/urandom , it first tries to get random data using the deprecated sysctl syscall, and if that fails (which will start happening once sysctl is finally removed), it falls back to a truly scary-looking function (lines 306-517) that attempts to get entropy from sketchy sources such as the PID, time of day, memory addresses, and other properties of the running process. OpenSSL is safer for two reasons: If OpenSSL can't open /dev/urandom , RAND_bytes returns an error code. Of course the programmer has to check the return value, which many probably don't, but at least OpenSSL allows a competent programmer to use it securely, unlike LibreSSL which will silently return sketchy entropy to even the most meticulous programmer. OpenSSL allows you to explicitly seed the PRNG by calling RAND_poll , which you can do before entering the chroot jail, avoiding the need to open /dev/urandom once in the jail. Indeed, this is how titus ensures it can use the PRNG from inside its highly-isolated chroot jail. Unfortunately, as discussed above, LibreSSL has turned RAND_poll into a no-op.

What should LibreSSL do? First, LibreSSL should raise an error if it can't get a good source of entropy. It can do better than OpenSSL by killing the process instead of returning an easily-ignored error code. In fact, there is already a disabled code path in LibreSSL (lines 154-156) that does this. It should be enabled. Second, LibreSSL should make RAND_poll reseed the PRNG as it does under OpenSSL. This will allow the programmer to guarantee safe and reliable operation after a fork and inside a chroot jail. This is especially important as LibreSSL aims to be a drop-in replacement for OpenSSL. Many properly-written programs have come to rely on OpenSSL's RAND_poll behavior for safe operation, and these programs will become less safe when linked with LibreSSL. Unfortunately, when I suggested the second change on Hacker News, a LibreSSL developer replied: The presence or need for a [RAND_poll] function should be considered a serious design flaw. I agree that in a perfect world, RAND_poll would not be necessary, and that its need is evidence of a design flaw. However, it is evidence of a design flaw not in the cryptographic library, but in the operating system. Unfortunately, Linux provides no reliable way to detect that a process has forked, and exposes entropy via a device file instead of a system call. LibreSSL has to work with what it's given, and on Linux that means RAND_poll is an unfortunate necessity.

Workaround If the LibreSSL developers don't fix RAND_poll , and you want your code to work safely with both LibreSSL and OpenSSL, then I recommend putting the following code after you fork or before you chroot (i.e. anywhere you would currently need RAND_poll ): unsigned char c ; if ( RAND_poll () != 1 ) { /* handle error */ } if ( RAND_bytes ( & c , 1 ) != 1 ) { /* handle error */ } In essence, always follow a call to RAND_poll with a request for one random byte. The RAND_bytes call will force LibreSSL to seed the PRNG if it's not already seeded, making it unnecessary to later open /dev/urandom from inside the chroot jail . It will also force LibreSSL to update the last seen PID, fixing the grandchild PID issue. (Edit: the LibreSSL PRNG periodically re-opens and re-reads /dev/urandom to mix in additional entropy, so unfortunately this won't avoid the need to open /dev/urandom from inside the chroot jail. However, as long as you have a good initial source of entropy, mixing in the sketchy entropy later isn't terrible.) I really hope it doesn't come to this. Programming with OpenSSL already requires dodging numerous traps and pitfalls, often by deploying obscure workarounds. The LibreSSL developers, through their well-intended effort to eliminate the pitfall of forgetting to call RAND_poll , have actually created a whole new pitfall with its own obscure workaround.