Usability of OpenSSL vs GNUPG

2019-12-14 Thread Dave via Gnupg-users
I've been playing around some with OpenSSL recently, and it seems to me that
the OpenSSL command structure is rather convoluted.  I've read a number of
articles, blog posts, etc. that criticize GNUPG and even make the case that
people should stop using it, in large part because of concerns around the
GNUPG command structure and general usability.  Yet I can't recall
encountering any similar complaints about OpenSSL.  I find this somewhat
curious, and am wondering if there are OpenSSL detractors out there that I
simply haven't come across or if the OpenSSL command structure isn't as
complicated as it seems to me.  Or if it seems to others that OpenSSL
doesn't get the same level of criticism as GNUPG does for usability,
although the tools seem to offer a generally similar user experience.  

 

I suppose that OpenSSL is geared toward a very technical and security-aware
user base, who aren't likely to complain about usability issues - while
GNUPG is a tool that could be used by all sorts of users, some of whom are
definitely not technically inclined or interested in details of information
security.  That alone could explain the difference, I suppose.  But I'm
wondering if anyone has any other thoughts around this topic.

 

Thanks,

 

Dave

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Re: Modern gnupg.conf setup

2019-12-14 Thread Damien Goutte-Gattat via Gnupg-users

On Sat, Dec 14, 2019 at 11:18:32PM +0100, Defiant wrote:

Hey, I recall back in the days there were lots of online tutorials about
how to strengthen your GnuPG configuration.


I don’t know which tutorials exactly you’re referring to, but I have 
seen several of them myself, and I have always had the feeling that they 
were written by people who couldn’t be bothered to check what GnuPG’s 
default configuration actually is before deciding it needed to be 
”strengthened”…




no-emit-version
no-comments


Not needed, those are the defaults.



export-options export-minimal


That’s up to you. Note, this does not actually “strengthen” anything.



keyid-format 0xlong
with-fingerprint


For information, the default is not to display any key ID (either short 
or long) but to display the full fingerprint instead (which makes 
displaying the key ID quite irrelevant).


Setting keyid-format to either “short” or “long” however has the effect 
of forcing GnuPG to display the key ID of *subkeys*, so if that’s 
something you need, you may keep that line.




list-options show-uid-validity
verify-options show-uid-validity


Already enabled by default.



personal-cipher-preferences AES256


The default is AES256, AES192, AES128, 3DES. Note that you cannot remove 
3DES which is mandatory as per the RFC 4880 (that’s the only algorithm 
which is guaranteed to be supported by any compliant OpenPGP 
implementation): even if you do not include it, GnuPG will silently add 
it back.


By removing AES192 and AES128, you’re actually increasing the risk that 
GnuPG will have to fallback to 3DES if AES256 is not supported by the 
other party. I don’t think this is what you want.




personal-digest-preferences SHA512


The default is SHA256, SHA384, SHA512, SHA-224, SHA1, with SHA1 being 
mandatory. Same problem as above: by limiting GnuPG’s options, you are 
increasing the risk of having to fallback to SHA1.




default-preference-list SHA512 SHA384 SHA256 SHA224 AES256 AES192 AES
TWOFISH ZLIB BZIP2 ZIP Uncompressed


This is almost exactly the default list, except that the default list 
does not include TWOFISH.




cipher-algo AES256
digest-algo SHA512
cert-digest-algo SHA512
compress-algo ZLIB


You are basically bypassing the whole preference-based mechanism used to 
select algorithms compatible with your recipients’ implementation.  
Almost certainly a bad idea unless you are operating in a context where 
you know you don’t need to care about interoperability (e.g. if you are 
only encrypting files for yourself).




disable-cipher-algo 3DES IDEA CAST5 Blowfish
weak-digest SHA1


3DES and SHA1 are mandatory as said above. The other algorithms are 
already not used by default.




s2k-cipher-algo AES256
s2k-digest-algo SHA512
s2k-mode 3
s2k-count 65011712


The default S2K mode is already 3 (iter+salt). As for the S2K count, for 
information the default is a value automatically determined by GPG Agent 
so that, on your computer, running the S2K algorithm will take ~100ms.



Overall I’d say most of your configuration is either uneeded or even 
counterproductive. I’ll quote GnuPG’s FAQ [1]:



Does GnuPG need to be ‘tuned’ before use?
No. GnuPG has sensible defaults right out of the box.



Cheers,

- Damien


[1] https://gnupg.org/faq/gnupg-faq.html#tuning


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Re: Modern gnupg.conf setup

2019-12-14 Thread Robert J. Hansen
> Hey, I recall back in the days there were lots of online tutorials about
> how to strengthen your GnuPG configuration. I'm setting up my gnupg.conf
> environment and I was wondering which of these options still apply for
> todays standards (GnuPG v2.2).

The standard advice still applies: unless you know what you're doing and
why it's necessary, just stick with the defaults.  :)  GnuPG 2.2 runs
quite well with a minimal config.  That said, I'll try to answer your
question!

> no-emit-version
> no-comments
> export-options export-minimal
> keyid-format 0xlong
> with-fingerprint

All still valid, all still useful.

> list-options show-uid-validity
> verify-options show-uid-validity

Valid.  Whether they're useful depends a lot on your personal needs.  I
don't have much use for them, but your needs might be different from mine.

> personal-cipher-preferences AES256
> personal-digest-preferences SHA512

Please don't: you're possibly harming interoperability.  Although AES256
is a strong and well-supported cipher, you'll find other people who
don't have it listed on their key preferences.  In that case, you will
silently degrade to 3DES, which is widely considered the worst cipher in
OpenPGP.  It's slow, it's inefficient, and it has inherent risks when
encrypting large files due to its 64-bit block size.

(It is also overengineered like a Soviet workers' housing bloc.  No one
is aware of any cryptographic attacks on it, other than when used with
very large files.  Still: slow and inefficient.)

Likewise, if you encounter someone who for whatever reason can't use
SHA512 (like if they're using the old, but still encountered, PGP 8.1),
you will silently degrade to using SHA-1, which I don't think you want
to do.

Instead, try this:

personal-cipher-preferences AES256 CAMELLIA256 TWOFISH AES192
CAMELLIA192 AES CAMELLIA128
personal-digest-preferences SHA512 SHA384 SHA256 SHA224 RIPEMD160

This way, if your correspondent can't use AES256 GnuPG will degrade to
the (strong, modern, fast) CAMELLIA algorithm.  If that's a no-go,
degrade to the (strong, modern, fast) 256-bit TWOFISH algorithm.  If the
256-bit ciphers are all a no-go, it degrades to 192-bit AES and
CAMELLIA, then the 128-bit variants.  Only if *no* modern cipher is
available will it then degrade to 3DES.

The same logic applies to SHA512.  It will exhaust all the modern hashes
before degrading to the (old, probably not very reliable any more, but
still better than SHA-1) RIPEMD160 algorithm, and only if all of them
are a no-go will it fall to SHA-1.

> default-preference-list SHA512 SHA384 SHA256 SHA224 AES256 AES192 AES
> TWOFISH ZLIB BZIP2 ZIP Uncompressed

Why do you prefer 128-bit AES over 256-bit TWOFISH?

> cipher-algo AES256
> digest-algo SHA512

*These are probably bad ideas.*  These say "screw what I just said about
my preference lists, ONLY use AES256 and SHA512" -- which can make your
message traffic non-interoperable with people who, for whatever reason,
cannot use AES256 or SHA512.

> cert-digest-algo SHA512

Still valid, still useful.

> compress-algo ZLIB

Scratch this for the same reasons as scratching "cipher-algo" and
"digest-algo".  Let GnuPG use a compression algorithm your correspondent
can actually use: don't force GnuPG to use one your correspondent can't use.

20 years ago it was widely believed compression before encryption was a
good idea.  Today that belief is pretty much shot, given how most file
formats already incorporate compression.

You can remove this line entirely.

> disable-cipher-algo 3DES IDEA CAST5 Blowfish

3DES is a MUST algorithm, according to the spec.  If you want to disable
the others that's your business -- but it's already implicit by not
including them in your personal-cipher-preferences.  This line can be
removed entirely.

> weak-digest SHA1

Again, SHA-1 is a MUST.

> s2k-cipher-algo AES256
> s2k-digest-algo SHA512

These are implicit given your personal-cipher-preferences and
personal-digest-preferences, and can be removed.

> s2k-mode 3

This is the default, and as such it can be removed.

> s2k-count 65011712

I have never found any use for cranking s2k-count this high.  I'd
suggest removing this line and using the defaults unless you have a
specific need for such a high count.

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Modern gnupg.conf setup

2019-12-14 Thread Defiant
Hey, I recall back in the days there were lots of online tutorials about
how to strengthen your GnuPG configuration. I'm setting up my gnupg.conf
environment and I was wondering which of these options still apply for
todays standards (GnuPG v2.2).

Thanks.



no-emit-version
no-comments
export-options export-minimal

keyid-format 0xlong
with-fingerprint

list-options show-uid-validity
verify-options show-uid-validity

personal-cipher-preferences AES256
personal-digest-preferences SHA512
default-preference-list SHA512 SHA384 SHA256 SHA224 AES256 AES192 AES
TWOFISH ZLIB BZIP2 ZIP Uncompressed

cipher-algo AES256
digest-algo SHA512
cert-digest-algo SHA512
compress-algo ZLIB

disable-cipher-algo 3DES IDEA CAST5 Blowfish
weak-digest SHA1

s2k-cipher-algo AES256
s2k-digest-algo SHA512
s2k-mode 3
s2k-count 65011712


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Re: gnupg private-keys encryption

2019-12-14 Thread Robert J. Hansen
> How can I control the encryption on the private-key?

Change the passphrase.  Just changing configuration file preferences
doesn't change the way the key is stored on disk.  It only says "the
next time you have to alter the way the key is stored on disk, use these
new parameters".

Changing the passphrase on the key will force GnuPG to write it out to
disk again, at which point your new preferences will take effect.

Warning: this information was correct for GnuPG 1.4 and 2.0.  I'm not
sure about 2.2, as I've never needed to do it on 2.2.

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