[openssl-users] Path Length Constraint ignored for Root and any self-issued certificate

Peter Magnusson blaufish.public.email at gmail.com
Mon Oct 8 14:47:46 UTC 2018


Tested mbedtls to see how other code bases handle thus.

mbedtls rejects the EvilCA certificate when connecting to openssl
s_server (as opposed to openssl c_client -verify that accepts the
connection).

Verify requested for (Depth 1):
cert. version     : 3
serial number     : 10:00
issuer name       : C=SE, ST=Root, L=Root, O=Root, OU=Root, CN=Root
subject name      : C=SE, ST=EvilCA, L=EvilCA, O=EvilCA, OU=EvilCA, CN=EvilCA
issued  on        : 2018-10-08 08:20:21
expires on        : 2028-10-05 08:20:21
signed using      : RSA with SHA-256
RSA key size      : 4096 bits
basic constraints : CA=true, max_pathlen=0
key usage         : Key Cert Sign, CRL Sign
  ! The certificate is not correctly signed by the trusted CA

The handshake fails after this error, mbedtls_ssl_handshake returned -9984.
On Mon, Oct 8, 2018 at 2:51 PM Peter Magnusson
<blaufish.public.email at gmail.com> wrote:
>
> sorry, typo on the verify line, this was what I should have written:
> VERIFY(max_path_length>0) error upon preparing transition from i=2
> (EvilCA) to i=2 (EvilServer).
> On Mon, Oct 8, 2018 at 2:47 PM Peter Magnusson
> <blaufish.public.email at gmail.com> wrote:
> >
> > That is not correct behaviour as far as I can understand.
> >
> > RFC5280 Certification Path Validation algorithm process from root to
> > leaf, i.e. (Root, EvilCA, EvilServer). 6.1.2 Initialization and 6.1.4
> > Preparation for Certificate i+1 is expected to occur upon Root
> > certificate, i.e. the following should be expected behaviour:
> > * max_path_length=n (initialisation)
> > * max_path_length=n-1 (first decrement)
> > * max_path_length=0 (copied from root certificate constraint)
> > * VERIFY(max_path_length>0) error upon preparing transition from i=1
> > (Root) to i=2 (EvilCA).
> >
> > OpenSSL does everything in a slightly different reverse algorithm, but
> > should perform the same controls and behaivor as the RFC imho.
> >
> > And aside from the RFC algorithm checking for this condition, it is
> > also analog with the description of the expected behaviour:
> >
> >    The pathLenConstraint field is meaningful only if the cA boolean is
> >    asserted and the key usage extension, if present, asserts the
> >    keyCertSign bit (Section 4.2.1.3).  In this case, it gives the
> >    maximum number of non-self-issued intermediate certificates that may
> >    follow this certificate in a valid certification path.  (Note: The
> >    last certificate in the certification path is not an intermediate
> >    certificate, and is not included in this limit.  Usually, the last
> >    certificate is an end entity certificate, but it can be a CA
> >    certificate.)  A pathLenConstraint of zero indicates that no non-
> >    self-issued intermediate CA certificates may follow in a valid
> >    certification path.  Where it appears, the pathLenConstraint field
> >    MUST be greater than or equal to zero.  Where pathLenConstraint does
> >    not appear, no limit is imposed.
> >
> > So my understanding is that the OpenSSL algorithm is confused and
> > fails to perform a check that is applicable to self-issued
> > certificates. The decrement of max_path_length (aka plen++ in OpenSSL
> > implementation) should not occur for self issued certificates, but the
> > validation of max_path_length>0 (aka plen>(constraint+1)) should
> > occur.
> > On Mon, Oct 8, 2018 at 1:27 PM J Decker <d3ck0r at gmail.com> wrote:
> > >
> > > It was my interpretation that 0 pathlen on the root self signed meant infinite.
> > > The pathlen only applies on the certs between root and the leaf (which obviously can be 0, and CA true or not, but bad form to say true I'd imagine.)
> > >
> > > On Mon, Oct 8, 2018 at 1:57 AM Peter Magnusson <blaufish.public.email at gmail.com> wrote:
> > >>
> > >> One more logic confusion in the OpenSSL Path Length Constraint check.
> > >> Any Path Length Constraint set by Root (or any other Self-Issued
> > >> Certificate) is ignored.
> > >> Root cause appears to be !(x->ex_flags & EXFLAG_SI)=0 incorrectly
> > >> applied to the checker (i.e. the checker and the calculation logic
> > >> have been mixed up).
> > >>
> > >> https://github.com/blaufish/openssl-pathlen/tree/master/testcase_2
> > >>
> > >> openssl x509 -text -in root.pem | grep -a1 "X509v3 Basic"
> > >>                 Certificate Sign, CRL Sign
> > >>             X509v3 Basic Constraints: critical
> > >>                 CA:TRUE, pathlen:0
> > >> openssl x509 -text -in evilca.pem | grep -a1 "X509v3 Basic"
> > >>                 Certificate Sign, CRL Sign
> > >>             X509v3 Basic Constraints: critical
> > >>                 CA:TRUE, pathlen:0
> > >> openssl x509 -text -in evilserver.pem | grep -a1 "X509v3 Basic"
> > >>         X509v3 extensions:
> > >>             X509v3 Basic Constraints: critical
> > >>                 CA:FALSE
> > >> ----
> > >> openssl x509 -text -in root.pem | egrep -a1 "X509v3 .* Key Identifier"
> > >>         X509v3 extensions:
> > >>             X509v3 Subject Key Identifier:
> > >>                 49:39:72:82:78:39:E8:60:AD:17:79:83:DB:65:B8:5C:E6:A7:84:B5
> > >> --
> > >> --
> > >>                 49:39:72:82:78:39:E8:60:AD:17:79:83:DB:65:B8:5C:E6:A7:84:B5
> > >>             X509v3 Authority Key Identifier:
> > >>
> > >> keyid:49:39:72:82:78:39:E8:60:AD:17:79:83:DB:65:B8:5C:E6:A7:84:B5
> > >> openssl x509 -text -in evilca.pem | grep -a1 "X509v3 .* Key Identifier"
> > >>         X509v3 extensions:
> > >>             X509v3 Subject Key Identifier:
> > >>                 B6:B4:75:66:18:B5:D2:4F:57:10:53:93:4F:CD:51:71:A4:27:84:7C
> > >> --
> > >> --
> > >>                 B6:B4:75:66:18:B5:D2:4F:57:10:53:93:4F:CD:51:71:A4:27:84:7C
> > >>             X509v3 Authority Key Identifier:
> > >>
> > >> keyid:49:39:72:82:78:39:E8:60:AD:17:79:83:DB:65:B8:5C:E6:A7:84:B5
> > >> openssl x509 -text -in evilserver.pem | egrep -a1 "X509v3 .* Key Identifier"
> > >>                 TLS Web Server Authentication
> > >>             X509v3 Subject Key Identifier:
> > >>                 03:C6:48:91:09:73:F5:DF:EF:B5:9D:A4:66:00:16:C3:E9:DB:99:EE
> > >> --
> > >> --
> > >>                 03:C6:48:91:09:73:F5:DF:EF:B5:9D:A4:66:00:16:C3:E9:DB:99:EE
> > >>             X509v3 Authority Key Identifier:
> > >>
> > >> keyid:B6:B4:75:66:18:B5:D2:4F:57:10:53:93:4F:CD:51:71:A4:27:84:7C
> > >> ----
> > >> ../openssl-1.1.1/apps/openssl verify -show_chain -verbose -CAfile
> > >> root.pem -untrusted evilca.pem evilserver.pem
> > >> ******* important variables *******
> > >> *** check_chain_extensions:524 i=0
> > >> *** check_chain_extensions:525 plen=0
> > >> *** check_chain_extensions:526 x->ex_pathlen=-1
> > >> ******* if statement components *******
> > >> *** check_chain_extensions:528 i > 1=0
> > >> *** check_chain_extensions:529 !(x->ex_flags & EXFLAG_SI)=1
> > >> *** check_chain_extensions:530 (x->ex_pathlen != -1)=0
> > >> *** check_chain_extensions:531 (plen > (x->ex_pathlen +
> > >> proxy_path_length + 1))=0
> > >> ******* important variables *******
> > >> *** check_chain_extensions:524 i=1
> > >> *** check_chain_extensions:525 plen=1
> > >> *** check_chain_extensions:526 x->ex_pathlen=0
> > >> ******* if statement components *******
> > >> *** check_chain_extensions:528 i > 1=0
> > >> *** check_chain_extensions:529 !(x->ex_flags & EXFLAG_SI)=1
> > >> *** check_chain_extensions:530 (x->ex_pathlen != -1)=1
> > >> *** check_chain_extensions:531 (plen > (x->ex_pathlen +
> > >> proxy_path_length + 1))=0
> > >> ******* important variables *******
> > >> *** check_chain_extensions:524 i=2
> > >> *** check_chain_extensions:525 plen=2
> > >> *** check_chain_extensions:526 x->ex_pathlen=0
> > >> ******* if statement components *******
> > >> *** check_chain_extensions:528 i > 1=1
> > >> *** check_chain_extensions:529 !(x->ex_flags & EXFLAG_SI)=0
> > >> *** check_chain_extensions:530 (x->ex_pathlen != -1)=1
> > >> *** check_chain_extensions:531 (plen > (x->ex_pathlen +
> > >> proxy_path_length + 1))=1
> > >> evilserver.pem: OK
> > >> Chain:
> > >> depth=0: C = SE, ST = EvilServer, L = EvilServer, O = EvilServer, OU =
> > >> EvilServer, CN = EvilServer (untrusted)
> > >> depth=1: C = SE, ST = EvilCA, L = EvilCA, O = EvilCA, OU = EvilCA, CN
> > >> = EvilCA (untrusted)
> > >> depth=2: C = SE, ST = Root, L = Root, O = Root, OU = Root, CN = Root
> > >> --
> > >> openssl-users mailing list
> > >> To unsubscribe: https://mta.openssl.org/mailman/listinfo/openssl-users
> > >
> > > --
> > > openssl-users mailing list
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