10 ms·

The sorry state of OpenSSL usability (2017)

161 points by anchpop 7y ago

avoidwork 7y ago
`openssl help` ... the macos version hides the `Invalid command '--help'; type "help" for a list.` message.
- guitarbill 7y ago
  that's kind of annoying. at the same time, this also underscores the issue of usability. why not alias "--help" to "help"? yes, i know even critical open source projects are extremely underfunded. perversely, the lack of funding meant that there weren't enough people to review code, which meant contributing was difficult - at least according to this article from 2014 shortly after heartbleed: https://arstechnica.com/information-technology/2014/04/tech-giants-chastened-by-heartbleed-finally-agree-to-fund-openssl/ https://arstechnica.com/information-technology/2014/04/tech-...
  - JdeBP 7y ago
    Note that part of the problem is the erroneous assumption that "--help" is ubiquitous. It isn't, in practice. It's a GNUism that one does not find very often in the BSD world.
    - guitarbill 7y ago
      fair enough, but still: how much effort would it be to support both?
bromonkey 7y ago
manpages for openssl (`man openssl`) exist on Linux + Solaris + BSD, this seems like a mac usability issue to me...
- CaliforniaKarl 7y ago
  Apple deprecated OpenSSL in macOS some time ago, directing people to their Core Crypto framework instead. See http://stackoverflow.com/questions/7406946/why-is-apple-deprecating-openssl-in-macos-10-7-lion http://stackoverflow.com/questions/7406946/why-is-apple-depr... for more info and links
- mls-pl 7y ago
  it's not quite true - on latest macOS (10.14.5), on openssl based on LibreSSL 2.6.5 there's complete man page available - but, the funniest thing, it's dated on... today
JohnAtCC 7y ago
Stop your bitching. YOU fix it.
CaliforniaKarl 7y ago
I think this should be retitled to "The sorry state of OpenSSL usability [on macOS]", because the author is using the built-in OpenSSL on macOS (which, as is eventually discovered, isn't actually OpenSSL). If you want to use OpenSSL on macOS, I suggest using the OpenSSL provided either in Brew or in MacPorts. That will give you a fully-functional setup (including help and man pages).
- tedivm 7y ago
  Outside of the man page issue all of the complaints from the author apply to all platforms that have openssl.
  - kevin_b_er 7y ago
    > Users matter: try doing some usability testing. Try adding some help text and man pages, instead of hijacking the wiki webpage of a different SSL project. And stop forking OpenSSL; you’re just making things worse. 1. Apple is not usability testing this 3 year old version of a fork of openssl, because they're not supporting it at all. 2. help text not available because its an apple supplied fork. openssl does tell you to use 'help' 3. man pages do exist. Just not installed by apple like author expected 4. and stop forking OpenSSL; BSD project forked it and Apple wants BSD over anything else because they can put the software in their closed platforms. Even if libressl were on the up and up, Apple's still got a version from 2016 installed. Those are all Apple problems, not openssl problems.
    - geggam 7y ago
      5. Follow the code commits of the LibreSSL fork and if you continue to use OpenSSL and not LibreSSL at least you will know the various issues you are going to have.
    - tedivm 7y ago
      1. The OpenSSL API hasn't changed, and if Apple changed it on their own that would break more things 2. The issue the author complained about was `openssl --help` not working, and it doesn't work on any platform (because he got the command wrong). `openssl help` does work on OSX (I literally just tested it). 3. Yeah, that's the one issue we agree is an Apple issue. 4. Apple didn't make LibreSSL. Other systems besides Apple use LibreSSL, and the authors complaints about their lack of documentation are relevant regardless of what Apple does.
mtgx 7y ago
Use Noise then: https://noiseprotocol.org/ https://noiseprotocol.org/ https://github.com/mcginty/snow https://github.com/mcginty/snow
eloy 7y ago
> And stop forking OpenSSL; you’re just making things worse. Yeah no. OpenBSD developers did a really good job by improving the codebase of OpenSSL. See also some of their presentations: https://www.libressl.org/papers.html https://www.libressl.org/papers.html
- crescentfresh 7y ago
  > by improving the codebase of OpenSSL Just to clarify: LibreSSL forked OpenSSL [1]. By definition they did not improve the codebase of OpenSSL. [1] https://en.wikipedia.org/wiki/LibreSSL https://en.wikipedia.org/wiki/LibreSSL
  - zwerdlds 7y ago
    Didnt most of their changes get merged back?
    - aomix 7y ago
      Most of the LibreSSL changes were removing features or platform support so I don't know how many of their changes were desired or applicable to OpenSSL.
    - crescentfresh 7y ago
      Source on this?
minusf 7y ago
libressl has documentation. it's an OpenBSD project so you use the man pages. http://man.openbsd.org/openssl http://man.openbsd.org/openssl
- mhb_eng 7y ago
  Unfortunately, libressl is not FIPS 140-2 compliant, so you can't leverage it for open source development of secure applications for the US government (though this is more to do with the certification headache than a fault of libressl itself)
  - snazz 7y ago
    This is not a priority at all for the OpenBSD developers. Most of them are Canadian anyway, as I understand it.
    - zeveb 7y ago
      Canada actually respects FIPS 140-2 certification (and cooperates in certifying implementations!), so this would very much be relevant in a Canadian context.
    - upofadown 7y ago
      That is actually understating it. The libressl developers purged the code base of the FIPS stuff as part of a policy. From here: * https://marc.info/?l=openbsd-misc&m=139819485423701&w=2 https://marc.info/?l=openbsd-misc&m=139819485423701&w=2 "Note that FIPS mode isn't just worthless, it's actively harmful."
      - compuguy 7y ago
        Unfortunately if you work with the US Government, there are situations where FIPS mode is required. This is why RHEL and CentOS still use OpenSSL...
  - rkeene2 7y ago
    Yes, this is why I had to stick to OpenSSL for my Linux distribution even though I would have preferred LibreSSL.
beefhash 7y ago
> OpenSSL decided to use a “512 bit long modulus”, the default. We’re told: “don’t roll your own crypto; instead trust standard tools like OpenSSL”. The modulus length is a good example of why: a wrong value results in a trivially breakable key, and you the user shouldn’t need to know what the right value is. So OpenSSL chooses a sensible modulus length for you. Checking the OpenBSD man page for the LibreSSL genrsa, it does seem to generate 2048-bit RSA keys by default[1]. Perhaps Apple just stuck with an older default (for backwards compat) or perhaps this wasn't changed yet in the old version of LibreSSL that Apple uses? [1] https://man.openbsd.org/openssl#GENRSA https://man.openbsd.org/openssl#GENRSA
- JdeBP 7y ago
  2.2.7 came out in May 2016. The switch to 2048 bits was in May 2014. * https://github.com/libressl-portable/openbsd/commit/30eb68d7caa1f7d4cf5dafa69d294567f5213500#diff-a249ba52ce01b7d5770a4e6f88d10640 https://github.com/libressl-portable/openbsd/commit/30eb68d7...
ergothus 7y ago
A lot of comments here about LibreSSL and Apple vs OpenSSL. Which is fine, that was my immediate reaction. But do the criticisms re:weak defaults, unlabeled deprecated commands, and uninformative output apply? Because I'll admit - every time I have to use (some version of) openSSL I google for the command I need and blindly use it. The commands are cryptic and meaningless. If this is true outside of LibreSSL, that definitely sounds like Apple is NOT the problem in this case (though certainly not helping)
- gipp 7y ago
  Yeah the accessibility of the manpages was clearly the least significant objection by far, but yours is the first comment about anything else.
- tialaramex 7y ago
  As someone who actually understands what is going on here I only partly agree. The commands aren't meaningless, but OpenSSL approaches the problem from a perspective that isn't what any ordinary user will want. Imagine you want to post a package to Brazil. You see a shop selling postage stamps - perfect. But of course such a shop is for stamp collectors. They've got lots of Brazilian stamps (you don't need those at all). They've got stamps from every decade (you need current stamps). They have rare stamps (you don't want to pay extra!) and they have lots of used stamps (no longer valid). Until relatively recently OpenSSL would default to creating CSRs by urging you to fill out largely irrelevant X.500 Distinguished Name and not even mention SAN dnsNames even though most users who want a CSR want it for a TLS server (e.g. web server) where the former is unimportant and the latter is vital. When it comes to writing TLS client software you probably know the name of the server you want to talk to. A sane API would let you tell the library this once and do all the rest for you. But OpenSSL reflects the interesting (to stamp collectors) half dozen different places that server names are involved in different versions of the protocols, not this sane but boring API. If you are a student of cryptographic history OpenSSL is great. If you are a application developer it's... poor. If you're a regular end user it's awful.
  - ergothus 7y ago
brynet 7y ago
> Unfortunately, http://www.libressl.org/ http://www.libressl.org/ won’t help you either, because there literally isn’t any documentation of LibreSSL. This is untrue. The front page contains links to the documentation inline, OpenBSD/LibreSSL converted all of OpenSSL's awful perlpod documentation to semantic mdoc(5) markup, and even wrote new man pages for functions completely undocumented by OpenSSL. See Ingo Schwarze' EuroBSDCon 2018 talk "Better documentation - on the web and for LibreSSL" https://www.openbsd.org/papers/eurobsdcon2018-mandoc.pdf https://www.openbsd.org/papers/eurobsdcon2018-mandoc.pdf https://youtu.be/jwfN7S1-fRA https://youtu.be/jwfN7S1-fRA And earlier writeups from 2016. https://undeadly.org/cgi?action=article;sid=20161215221715 https://undeadly.org/cgi?action=article;sid=20161215221715 It's been a long road to improve the documentation, and it's substantially better than OpenSSL.
- ivl 7y ago
  You're not wrong, but there's a big middleground here. To a user without some curiosity this: LibreSSL releases contain several parts: libcrypto: a library of cryptography fundamentals libssl: a TLS library libtls: a new TLS library, designed to make it easier to write foolproof applications Various utilities such as openssl(1), nc(1), and ocspcheck(8). With libcrypto, libssl, libtls, openssl, nc, and ocspcheck all links pointing to man.openbsd.org/x does not scream documentation. The words 'documentation' or 'manual' appear nowhere on the libressl home page. They are undoubtedly present, but unless you click around assuming those aren't links to individual components, you wouldn't think so at a glance.
  - thepangolino 7y ago
    So what your saying the issue is libressl should put a link to the documentation on their front page? Sounds like a fair request. Perhaps someone should send them an email to let them know. That being said, you put a finger on the main issue most security and privacy tool have: user friendliness.
    - jandrese 7y ago
      In many ways user friendliness corresponds directly with real life security level. Lots of compromises aren't due to a deficiency in the code, but someone using it incorrectly. Maybe by assuming the defaults are sane, or not understanding the implications of some of the technical jargon in the manual. Remember Sony, a 60 billion dollar company, completely fubared the DRM on the Playstation 2 because a developer didn't understand what an IV is. And you go through the OpenSSL docs and it will tell you where to supply your IV without ever explaining what it is. All it needs is a single paragraph explaining the best practices, probably 5 or 10 lines in the manual.
closeparen 7y ago
The Go crypto package is really a treat. I found it scary and incomprehensible to do anything with certificates using the OpenSSL command line, convenience wrappers notwithstanding. Adam Langley’s work shows what a reasonably ergonomic and approachable interface for this domain could look like. Turns out that issuing certificates doesn’t have to be dark magic.
deleted 7y ago
[deleted]
garyb2 7y ago
Just tried openssl genrsa on my Mac: openssl genrsa Generating RSA private key, 2048 bit long modulus openssl version LibreSSL 2.6.5 So maybe install Mac updates?
- JdeBP 7y ago
  As pointed out in this discussion elsewhere, this is an article written in 2017 and never updated. * https://github.com/jameshfisher/jameshfisher.com/commits/master/_posts/2017-12-02-the-sorry-state-of-openssl-usability.md https://github.com/jameshfisher/jameshfisher.com/commits/mas...
CiPHPerCoder 7y ago
My question is: Why are you trying to use RSA at all? It's 2019! I can't think of anyone who seriously recommends RSA anymore. Switch to elliptic curve cryptography, where footbullets like a 512-bit RSA key offer aren't even on the table.
- bromonkey 7y ago
  This article was written years ago
  - CiPHPerCoder 7y ago
    Oh! It really should have [2017] in the title, then.
- recursive 7y ago
  > Why are you trying to use RSA at all? Probably because you have to use something, and it's not obvious which things have footbullets and which don't.
  - CiPHPerCoder 7y ago
    https://latacora.micro.blog/2018/04/03/cryptographic-right-answers.html https://latacora.micro.blog/2018/04/03/cryptographic-right-a... https://paragonie.com/blog/2017/06/libsodium-quick-reference-quick-comparison-similar-functions-and-which-one-use https://paragonie.com/blog/2017/06/libsodium-quick-reference... https://libsodium.gitbook.io/doc/bindings_for_other_languages https://libsodium.gitbook.io/doc/bindings_for_other_language... It's a lot easier in 2019 than it was years ago.
- x38iq84n 7y ago
  Sometimes it is a necessity to accommodate for various networking gear as load balancers, wireless controllers etc as RSA may be the only thing that they support.
parliament32 7y ago
All of these complaints are MacOS problems. On my Debian laptop, "openssl --help" actually displays some help (despite --help not being a real flag), "man openssl" works as expected, and "openssl genrsa" uses a 2048-bit modulus... and "openssl verison" confirms it's actually openssl.
low_key 7y ago
Sure, the commands are difficult to digest. Where it gets truly awful, though, is trying to write a program that uses the openssl library.
GTP 7y ago
If on macOS openSSL is replaced by LibreSSL isn't OpenSSL's fault, and I also think that the title "The sorry state of OpenSSL usability" isn't right since it's actually talking about LibreSSL. By the way I've just ran "man openssl" on a Linux box and got the manual for OpenSSL, so I'm thinking that this could be more a problem of macOS than OpenSSL. Of course I agree that the online docs should say if something is deprecated or is using a default value that is no longer safe, but the rest of the article doesn't seem well made to me
notacoward 7y ago
If you think the user interface is bad, try the programmer interface. OMG. Layer upon layer of nonsensical objects to initialize and chain together, each with a bazillion options and no decent documentation about which few are secure. No decent interface for getting the specifics about an error. Not thread-safe unless you create your own array of locking functions (which must meet barely-documented requirements) and pass them in for the library to call at random times. Weird WANT_READ/WANT_WRITE nonsense that makes integration with a bog-standard poll/select loop more difficult. It's like the OpenSSL developers think SSL is the main thing your program should be doing and you're lucky they let any other functionality exist in the same program. The phrase "fractal of bad design" was originally invented for PHP but applies to OpenSSL just as much.
- alias_neo 7y ago
  The developer interface is _much_ worse than the user interface. At least the user interface had shell completions to guide your guess work. As you suggested, having to initialise a bunch of things in some undisclosed order is bordering on meddling with the dark arts, good luck tearing it all down again safely. Then let's say you want to streaming-encrypt something on the fly, good luck understanding the correct way to chain BIOs and what exactly the behaviour for seeking, buffering, writing, closing, opening, decrypting, reading, popping BIOs and then working with the remainder of the chain, before pushing a BIO back on is. I wrote a steaming data encryptor a little while back using openssl, just in C, it works fine now but the majority of my reading was existing implementations on the web and some out-of-date blogs coupled with some, sometimes-correct documentation and just pain trial-and-error paired with my good old friend Valgrind. Unfortunately, in some industries it's go-FIPS-or-go-home, so we don't even have the choice of using a fork or an alternative at times.

161 points by anchpop 7y ago

avoidwork 7y ago

`openssl help` ... the macos version hides the `Invalid command '--help'; type "help" for a list.` message.

guitarbill 7y ago
that's kind of annoying. at the same time, this also underscores the issue of usability. why not alias "--help" to "help"? yes, i know even critical open source projects are extremely underfunded. perversely, the lack of funding meant that there weren't enough people to review code, which meant contributing was difficult - at least according to this article from 2014 shortly after heartbleed: https://arstechnica.com/information-technology/2014/04/tech-giants-chastened-by-heartbleed-finally-agree-to-fund-openssl/ https://arstechnica.com/information-technology/2014/04/tech-...
- JdeBP 7y ago
  Note that part of the problem is the erroneous assumption that "--help" is ubiquitous. It isn't, in practice. It's a GNUism that one does not find very often in the BSD world.
  - guitarbill 7y ago
    fair enough, but still: how much effort would it be to support both?

bromonkey 7y ago

manpages for openssl (`man openssl`) exist on Linux + Solaris + BSD, this seems like a mac usability issue to me...

CaliforniaKarl 7y ago
Apple deprecated OpenSSL in macOS some time ago, directing people to their Core Crypto framework instead. See http://stackoverflow.com/questions/7406946/why-is-apple-deprecating-openssl-in-macos-10-7-lion http://stackoverflow.com/questions/7406946/why-is-apple-depr... for more info and links
mls-pl 7y ago
it's not quite true - on latest macOS (10.14.5), on openssl based on LibreSSL 2.6.5 there's complete man page available - but, the funniest thing, it's dated on... today

JohnAtCC 7y ago

Stop your bitching. YOU fix it.

CaliforniaKarl 7y ago

I think this should be retitled to "The sorry state of OpenSSL usability [on macOS]", because the author is using the built-in OpenSSL on macOS (which, as is eventually discovered, isn't actually OpenSSL). If you want to use OpenSSL on macOS, I suggest using the OpenSSL provided either in Brew or in MacPorts. That will give you a fully-functional setup (including help and man pages).

tedivm 7y ago
Outside of the man page issue all of the complaints from the author apply to all platforms that have openssl.
- kevin_b_er 7y ago
  > Users matter: try doing some usability testing. Try adding some help text and man pages, instead of hijacking the wiki webpage of a different SSL project. And stop forking OpenSSL; you’re just making things worse. 1. Apple is not usability testing this 3 year old version of a fork of openssl, because they're not supporting it at all. 2. help text not available because its an apple supplied fork. openssl does tell you to use 'help' 3. man pages do exist. Just not installed by apple like author expected 4. and stop forking OpenSSL; BSD project forked it and Apple wants BSD over anything else because they can put the software in their closed platforms. Even if libressl were on the up and up, Apple's still got a version from 2016 installed. Those are all Apple problems, not openssl problems.
  - geggam 7y ago
    5. Follow the code commits of the LibreSSL fork and if you continue to use OpenSSL and not LibreSSL at least you will know the various issues you are going to have.
  - tedivm 7y ago
    1. The OpenSSL API hasn't changed, and if Apple changed it on their own that would break more things 2. The issue the author complained about was `openssl --help` not working, and it doesn't work on any platform (because he got the command wrong). `openssl help` does work on OSX (I literally just tested it). 3. Yeah, that's the one issue we agree is an Apple issue. 4. Apple didn't make LibreSSL. Other systems besides Apple use LibreSSL, and the authors complaints about their lack of documentation are relevant regardless of what Apple does.

mtgx 7y ago

Use Noise then: https://noiseprotocol.org/ https://noiseprotocol.org/ https://github.com/mcginty/snow https://github.com/mcginty/snow

eloy 7y ago

> And stop forking OpenSSL; you’re just making things worse. Yeah no. OpenBSD developers did a really good job by improving the codebase of OpenSSL. See also some of their presentations: https://www.libressl.org/papers.html https://www.libressl.org/papers.html

crescentfresh 7y ago
> by improving the codebase of OpenSSL Just to clarify: LibreSSL forked OpenSSL [1]. By definition they did not improve the codebase of OpenSSL. [1] https://en.wikipedia.org/wiki/LibreSSL https://en.wikipedia.org/wiki/LibreSSL
- zwerdlds 7y ago
  Didnt most of their changes get merged back?
  - aomix 7y ago
    Most of the LibreSSL changes were removing features or platform support so I don't know how many of their changes were desired or applicable to OpenSSL.
  - crescentfresh 7y ago
    Source on this?

minusf 7y ago

libressl has documentation. it's an OpenBSD project so you use the man pages. http://man.openbsd.org/openssl http://man.openbsd.org/openssl

mhb_eng 7y ago
Unfortunately, libressl is not FIPS 140-2 compliant, so you can't leverage it for open source development of secure applications for the US government (though this is more to do with the certification headache than a fault of libressl itself)
- snazz 7y ago
  This is not a priority at all for the OpenBSD developers. Most of them are Canadian anyway, as I understand it.
  - zeveb 7y ago
    Canada actually respects FIPS 140-2 certification (and cooperates in certifying implementations!), so this would very much be relevant in a Canadian context.
  - upofadown 7y ago
    That is actually understating it. The libressl developers purged the code base of the FIPS stuff as part of a policy. From here: * https://marc.info/?l=openbsd-misc&m=139819485423701&w=2 https://marc.info/?l=openbsd-misc&m=139819485423701&w=2 "Note that FIPS mode isn't just worthless, it's actively harmful."
    - compuguy 7y ago
      Unfortunately if you work with the US Government, there are situations where FIPS mode is required. This is why RHEL and CentOS still use OpenSSL...
- rkeene2 7y ago
  Yes, this is why I had to stick to OpenSSL for my Linux distribution even though I would have preferred LibreSSL.

beefhash 7y ago

> OpenSSL decided to use a “512 bit long modulus”, the default. We’re told: “don’t roll your own crypto; instead trust standard tools like OpenSSL”. The modulus length is a good example of why: a wrong value results in a trivially breakable key, and you the user shouldn’t need to know what the right value is. So OpenSSL chooses a sensible modulus length for you. Checking the OpenBSD man page for the LibreSSL genrsa, it does seem to generate 2048-bit RSA keys by default[1]. Perhaps Apple just stuck with an older default (for backwards compat) or perhaps this wasn't changed yet in the old version of LibreSSL that Apple uses? [1] https://man.openbsd.org/openssl#GENRSA https://man.openbsd.org/openssl#GENRSA

JdeBP 7y ago
2.2.7 came out in May 2016. The switch to 2048 bits was in May 2014. * https://github.com/libressl-portable/openbsd/commit/30eb68d7caa1f7d4cf5dafa69d294567f5213500#diff-a249ba52ce01b7d5770a4e6f88d10640 https://github.com/libressl-portable/openbsd/commit/30eb68d7...

ergothus 7y ago

A lot of comments here about LibreSSL and Apple vs OpenSSL. Which is fine, that was my immediate reaction. But do the criticisms re:weak defaults, unlabeled deprecated commands, and uninformative output apply? Because I'll admit - every time I have to use (some version of) openSSL I google for the command I need and blindly use it. The commands are cryptic and meaningless. If this is true outside of LibreSSL, that definitely sounds like Apple is NOT the problem in this case (though certainly not helping)

gipp 7y ago
Yeah the accessibility of the manpages was clearly the least significant objection by far, but yours is the first comment about anything else.
tialaramex 7y ago
As someone who actually understands what is going on here I only partly agree. The commands aren't meaningless, but OpenSSL approaches the problem from a perspective that isn't what any ordinary user will want. Imagine you want to post a package to Brazil. You see a shop selling postage stamps - perfect. But of course such a shop is for stamp collectors. They've got lots of Brazilian stamps (you don't need those at all). They've got stamps from every decade (you need current stamps). They have rare stamps (you don't want to pay extra!) and they have lots of used stamps (no longer valid). Until relatively recently OpenSSL would default to creating CSRs by urging you to fill out largely irrelevant X.500 Distinguished Name and not even mention SAN dnsNames even though most users who want a CSR want it for a TLS server (e.g. web server) where the former is unimportant and the latter is vital. When it comes to writing TLS client software you probably know the name of the server you want to talk to. A sane API would let you tell the library this once and do all the rest for you. But OpenSSL reflects the interesting (to stamp collectors) half dozen different places that server names are involved in different versions of the protocols, not this sane but boring API. If you are a student of cryptographic history OpenSSL is great. If you are a application developer it's... poor. If you're a regular end user it's awful.
- ergothus 7y ago

brynet 7y ago

> Unfortunately, http://www.libressl.org/ http://www.libressl.org/ won’t help you either, because there literally isn’t any documentation of LibreSSL. This is untrue. The front page contains links to the documentation inline, OpenBSD/LibreSSL converted all of OpenSSL's awful perlpod documentation to semantic mdoc(5) markup, and even wrote new man pages for functions completely undocumented by OpenSSL. See Ingo Schwarze' EuroBSDCon 2018 talk "Better documentation - on the web and for LibreSSL" https://www.openbsd.org/papers/eurobsdcon2018-mandoc.pdf https://www.openbsd.org/papers/eurobsdcon2018-mandoc.pdf https://youtu.be/jwfN7S1-fRA https://youtu.be/jwfN7S1-fRA And earlier writeups from 2016. https://undeadly.org/cgi?action=article;sid=20161215221715 https://undeadly.org/cgi?action=article;sid=20161215221715 It's been a long road to improve the documentation, and it's substantially better than OpenSSL.

ivl 7y ago
You're not wrong, but there's a big middleground here. To a user without some curiosity this: LibreSSL releases contain several parts: libcrypto: a library of cryptography fundamentals libssl: a TLS library libtls: a new TLS library, designed to make it easier to write foolproof applications Various utilities such as openssl(1), nc(1), and ocspcheck(8). With libcrypto, libssl, libtls, openssl, nc, and ocspcheck all links pointing to man.openbsd.org/x does not scream documentation. The words 'documentation' or 'manual' appear nowhere on the libressl home page. They are undoubtedly present, but unless you click around assuming those aren't links to individual components, you wouldn't think so at a glance.
- thepangolino 7y ago
  So what your saying the issue is libressl should put a link to the documentation on their front page? Sounds like a fair request. Perhaps someone should send them an email to let them know. That being said, you put a finger on the main issue most security and privacy tool have: user friendliness.
  - jandrese 7y ago
    In many ways user friendliness corresponds directly with real life security level. Lots of compromises aren't due to a deficiency in the code, but someone using it incorrectly. Maybe by assuming the defaults are sane, or not understanding the implications of some of the technical jargon in the manual. Remember Sony, a 60 billion dollar company, completely fubared the DRM on the Playstation 2 because a developer didn't understand what an IV is. And you go through the OpenSSL docs and it will tell you where to supply your IV without ever explaining what it is. All it needs is a single paragraph explaining the best practices, probably 5 or 10 lines in the manual.

closeparen 7y ago

The Go crypto package is really a treat. I found it scary and incomprehensible to do anything with certificates using the OpenSSL command line, convenience wrappers notwithstanding. Adam Langley’s work shows what a reasonably ergonomic and approachable interface for this domain could look like. Turns out that issuing certificates doesn’t have to be dark magic.

deleted 7y ago

[deleted]

garyb2 7y ago

Just tried openssl genrsa on my Mac: openssl genrsa Generating RSA private key, 2048 bit long modulus openssl version LibreSSL 2.6.5 So maybe install Mac updates?

JdeBP 7y ago
As pointed out in this discussion elsewhere, this is an article written in 2017 and never updated. * https://github.com/jameshfisher/jameshfisher.com/commits/master/_posts/2017-12-02-the-sorry-state-of-openssl-usability.md https://github.com/jameshfisher/jameshfisher.com/commits/mas...

CiPHPerCoder 7y ago

My question is: Why are you trying to use RSA at all? It's 2019! I can't think of anyone who seriously recommends RSA anymore. Switch to elliptic curve cryptography, where footbullets like a 512-bit RSA key offer aren't even on the table.

bromonkey 7y ago
This article was written years ago
- CiPHPerCoder 7y ago
  Oh! It really should have [2017] in the title, then.
recursive 7y ago
> Why are you trying to use RSA at all? Probably because you have to use something, and it's not obvious which things have footbullets and which don't.
- CiPHPerCoder 7y ago
  https://latacora.micro.blog/2018/04/03/cryptographic-right-answers.html https://latacora.micro.blog/2018/04/03/cryptographic-right-a... https://paragonie.com/blog/2017/06/libsodium-quick-reference-quick-comparison-similar-functions-and-which-one-use https://paragonie.com/blog/2017/06/libsodium-quick-reference... https://libsodium.gitbook.io/doc/bindings_for_other_languages https://libsodium.gitbook.io/doc/bindings_for_other_language... It's a lot easier in 2019 than it was years ago.
x38iq84n 7y ago
Sometimes it is a necessity to accommodate for various networking gear as load balancers, wireless controllers etc as RSA may be the only thing that they support.

parliament32 7y ago

All of these complaints are MacOS problems. On my Debian laptop, "openssl --help" actually displays some help (despite --help not being a real flag), "man openssl" works as expected, and "openssl genrsa" uses a 2048-bit modulus... and "openssl verison" confirms it's actually openssl.

low_key 7y ago

Sure, the commands are difficult to digest. Where it gets truly awful, though, is trying to write a program that uses the openssl library.

GTP 7y ago

If on macOS openSSL is replaced by LibreSSL isn't OpenSSL's fault, and I also think that the title "The sorry state of OpenSSL usability" isn't right since it's actually talking about LibreSSL. By the way I've just ran "man openssl" on a Linux box and got the manual for OpenSSL, so I'm thinking that this could be more a problem of macOS than OpenSSL. Of course I agree that the online docs should say if something is deprecated or is using a default value that is no longer safe, but the rest of the article doesn't seem well made to me

notacoward 7y ago

If you think the user interface is bad, try the programmer interface. OMG. Layer upon layer of nonsensical objects to initialize and chain together, each with a bazillion options and no decent documentation about which few are secure. No decent interface for getting the specifics about an error. Not thread-safe unless you create your own array of locking functions (which must meet barely-documented requirements) and pass them in for the library to call at random times. Weird WANT_READ/WANT_WRITE nonsense that makes integration with a bog-standard poll/select loop more difficult. It's like the OpenSSL developers think SSL is the main thing your program should be doing and you're lucky they let any other functionality exist in the same program. The phrase "fractal of bad design" was originally invented for PHP but applies to OpenSSL just as much.

alias_neo 7y ago
The developer interface is _much_ worse than the user interface. At least the user interface had shell completions to guide your guess work. As you suggested, having to initialise a bunch of things in some undisclosed order is bordering on meddling with the dark arts, good luck tearing it all down again safely. Then let's say you want to streaming-encrypt something on the fly, good luck understanding the correct way to chain BIOs and what exactly the behaviour for seeking, buffering, writing, closing, opening, decrypting, reading, popping BIOs and then working with the remainder of the chain, before pushing a BIO back on is. I wrote a steaming data encryptor a little while back using openssl, just in C, it works fine now but the majority of my reading was existing implementations on the web and some out-of-date blogs coupled with some, sometimes-correct documentation and just pain trial-and-error paired with my good old friend Valgrind. Unfortunately, in some industries it's go-FIPS-or-go-home, so we don't even have the choice of using a fork or an alternative at times.