On 13/09/2018 03:24, Michael Wojcik wrote:
From: openssl-users [mailto:openssl-users-boun...@openssl.org] On Behalf
Of Jakob Bohm
Sent: Wednesday, September 12, 2018 17:18

Testing your OpenSSL download with the HTTPS security bites its
own tail, especially if your download tool uses an (older) version
of OpenSSL to check the connection.
And as I noted in my previous email, the HTTPS PKI is rubbish. Historically 
there have been numerous successful attacks on it, even in modes that do not 
involve user intervention.

It's better than nothing, but checking the PGP signature is defense in depth 
that does not rely solely on the integrity of the HTTPS PKI.

But unless you have an established personal list of GPG/PGP keys
you have checked against their holders in person yourself, checking
the HTTPS certificate of the OpenSSL.org web server is pretty much
all you can do to distinguish between a genuine and a fake first time
OpenSSL download (signatures on later downloads can be compared to
previous downloadsfor some degree of signature consistency).
There are plenty of other channels that can be used to validate the PGP public 
key used to confirm the signature of the OpenSSL tarball. None of them are 
secure in themselves, but by using multiple channels, the defender greatly 
increases the attacker's work factor and risk of discovery. That's the whole 
point of defense in depth.

It's not hard to learn how to install an OpenPGP implementation (most likely 
gpg) and use it to verify a detached signature. There are many tutorials 
available online. I don't think a lack of experience with PGP or gpg is a valid 
excuse for not validating the signature.

Of cause some real knowledge is needed to not use the OpenSSL source
code incorrectly, unless you are merely compiling other peoples
software exactly as instructed.
Yes. And this is a much more likely source of problems than a counterfeit 
OpenSSL distribution.

To make it clear, I am very experienced and do in fact check the gpg signature if possible.  I was trying to give good advice to the OP based on my experience
checking the only ways that the OpenSSL foundation provides.

The OpenPGP/GPG key servers that you suggested, by design, accept any made up key identity and thus provide no indication of validity, so just downloading the key from there is a non-solution to the problem of bootstrapping trust in
someones first OpenSSL download.

To my knowledge the only ways to check that the .asc file was signed with an
authorized release key are:

A) Trusting that the HTTPS connection to the download server is uncompromised,
  essentially treating at least the first such signature as a glorified
  .sha256 file.

B) Checking doc/fingerprints.txt in the previous tarball and hoping the OpenSSL   foundation double checks the correctness of that file before signing a new
  tarball.

C) Using the text (BUT NOT THE INSECURE LINKS) on
  https://www.openssl.org/community/omc.html
   But this lists some unauthorized keys, and also relies on that same HTTPS
  certificate.


Enjoy

Jakob
--
Jakob Bohm, CIO, Partner, WiseMo A/S.  https://www.wisemo.com
Transformervej 29, 2860 Søborg, Denmark.  Direct +45 31 13 16 10
This public discussion message is non-binding and may contain errors.
WiseMo - Remote Service Management for PCs, Phones and Embedded

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