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  1. Convert encrypted SSL test keys to PKCS#8 format

  1. Convert encrypted SSL test keys to PKCS#8 format

    Peter Eisentraut <peter@eisentraut.org> — 2023-08-22T08:07:05Z

    This is part of the larger project of allowing all test suites to pass 
in OpenSSL FIPS mode.  We had previously integrated several patches that 
avoid or isolate use of MD5 in various forms in the tests.  Now to 
another issue.

OpenSSL in FIPS mode rejects several encrypted private keys used in the 
test suites ssl and ssl_passphrase_callback.  The reason for this is 
explained in [0]:

 > Technically you shouldn't use keys created outside FIPS mode in FIPS
 > mode.
 >
 > In FIPS mode the "traditional" format is not supported because it used
 > MD5 for key derivation. The more standard PKCS#8 mode using SHA1 for
 > key derivation is use instead. You can convert keys using the pkcs8
 > command outside FIPS mode but again technically you aren't supposed
 > to...

[0]: 
https://groups.google.com/g/mailing.openssl.users/c/Sd5E8VY5O2s/m/QYGezoQeo84J

The affected files are

src/test/modules/ssl_passphrase_callback/server.key
src/test/ssl/ssl/client-encrypted-pem.key
src/test/ssl/ssl/server-password.key

A fix is to convert them from their existing PKCS#1 format to the PKCS#8 
format, like this:

openssl pkcs8 -topk8 -in 
src/test/modules/ssl_passphrase_callback/server.key -passin pass:FooBaR1 
-out src/test/modules/ssl_passphrase_callback/server.key.new -passout 
pass:FooBaR1
mv src/test/modules/ssl_passphrase_callback/server.key.new 
src/test/modules/ssl_passphrase_callback/server.key

etc.

(Fun fact: The above command also doesn't work if your OpenSSL 
installation is in FIPS mode because it will refuse to read the old file.)

We should also update the generation rules to generate the newer format, 
like this:

-   $(OPENSSL) rsa -aes256 -in server.ckey -out server.key -passout 
pass:$(PASS)
+   $(OPENSSL) pkey -aes256 -in server.ckey -out server.key -passout 
pass:$(PASS)

I have attached two patches, one to update the generation rules, and one 
where I have converted the existing test files.  (I didn't generate them 
from scratch, so for example 
src/test/modules/ssl_passphrase_callback/server.crt that corresponds to 
one of the keys does not need to be updated.)

To check that these new files are backward compatible, I have 
successfully tested them on CentOS 7 with the included version 1.0.2k.

It's also interesting that if you generate all private keys from scratch 
using the existing rules on a new OpenSSL version (3+), they will be 
generated in PKCS#8 format by default.  In those OpenSSL versions, the 
openssl-rsa command has a -traditional option to get the old format, but 
of course old OpenSSL versions don't have that.  As OpenSSL 3 gets more 
widespread, we might need to rethink these rules anyway to make sure we 
get consistent behavior.

  2. Re: Convert encrypted SSL test keys to PKCS#8 format

    Jacob Champion <jchampion@timescale.com> — 2023-08-22T19:02:02Z

    On Tue, Aug 22, 2023 at 1:07 AM Peter Eisentraut <peter@eisentraut.org> wrote:
> I have attached two patches, one to update the generation rules, and one
> where I have converted the existing test files.  (I didn't generate them
> from scratch, so for example
> src/test/modules/ssl_passphrase_callback/server.crt that corresponds to
> one of the keys does not need to be updated.)

Looks good from here. I don't have a FIPS setup right now, but the new
files pass tests on OpenSSL 1.0.2u, 1.1.1v, 3.0.2-0ubuntu1.10, and
LibreSSL 3.8. Tests continue to pass after a full clean and rebuild of
the sslfiles.

> It's also interesting that if you generate all private keys from scratch
> using the existing rules on a new OpenSSL version (3+), they will be
> generated in PKCS#8 format by default.  In those OpenSSL versions, the
> openssl-rsa command has a -traditional option to get the old format, but
> of course old OpenSSL versions don't have that.  As OpenSSL 3 gets more
> widespread, we might need to rethink these rules anyway to make sure we
> get consistent behavior.

Yeah. Looks like OpenSSL 3 also adds new v3 extensions to the
certificates... For now they look benign, but I assume someone's going
to run into weirdness at some point.

Thanks!
--Jacob

  3. Re: Convert encrypted SSL test keys to PKCS#8 format

    Peter Eisentraut <peter@eisentraut.org> — 2023-08-28T06:44:25Z

    On 22.08.23 21:02, Jacob Champion wrote:
> On Tue, Aug 22, 2023 at 1:07 AM Peter Eisentraut <peter@eisentraut.org> wrote:
>> I have attached two patches, one to update the generation rules, and one
>> where I have converted the existing test files.  (I didn't generate them
>> from scratch, so for example
>> src/test/modules/ssl_passphrase_callback/server.crt that corresponds to
>> one of the keys does not need to be updated.)
> 
> Looks good from here. I don't have a FIPS setup right now, but the new
> files pass tests on OpenSSL 1.0.2u, 1.1.1v, 3.0.2-0ubuntu1.10, and
> LibreSSL 3.8. Tests continue to pass after a full clean and rebuild of
> the sslfiles.

Committed, thanks.