Well, those attributes will work (minus the IKE one-it was not
recognized) but the Watchguard does not assign it with a type of
IPSec, so I've contacted Watchguard support to request the expected
extended attributes for this.  I will post a reply as soon as I know.

On Tue, Aug 26, 2008 at 1:41 PM, Kyle Hamilton <[EMAIL PROTECTED]> wrote:
> This is a bug, per RFC 4549.  Please submit a report to your vendor.
> (The semantics of the OIDs were never well-defined, and they have been
> obsoleted -- according to RFC4549, having keyUsage=digitalSignature
> and no EKU should work for IPsec.)
>
> In the [new_oids] section, add new lines:
>
> pkixeku=1.3.6.1.5.5.7.3
> ipsecendsystem=${pkixeku}.5
> ipsectunnel=${pkixeku}.6
> ipsecuser=${pkixeku}.7
>
> and then in [usr_cert] change your extendedKeyUsage line to:
>
> extendedKeyUsage=serverAuth,clientAuth,ipsecIKE,ipsecendsystem,ipsectunnel,ipsecuser
>
> This /should/ do it, but since I don't do anything with IPsec I can't
> test it.  My reference is
> http://www.alvestrand.no/objectid/1.3.6.1.5.5.7.3.html
>
> -Kyle H
>
> On Tue, Aug 26, 2008 at 1:17 PM, Chris Zimmerman
> <[EMAIL PROTECTED]> wrote:
>> Thanks to all of you in your assistance.  With the recommended changes
>> to the openssl.cnf file, I have successfully signed the CSR from the
>> Watchguard box and imported it as a web cert (the Type that the
>> Watchguard box sees).  However, in order to use it for VPN tunnels,
>> the device needs it to be a type IPSec.  What is the extended key
>> usage setting for that?
>>
>> On Tue, Aug 26, 2008 at 10:41 AM, Kyle Hamilton <[EMAIL PROTECTED]> wrote:
>>> [usr_cert] is the appropriate section.
>>>
>>> This is above the [v3_req] section, at least in the vanilla 0.9.8h sources.
>>>
>>> -Kyle H
>>>
>>> On Tue, Aug 26, 2008 at 10:33 AM, Chris Zimmerman
>>> <[EMAIL PROTECTED]> wrote:
>>>> What is the appropriate section?
>>>>
>>>> Sorry if this is a basic question, but I am working on improving my 
>>>> knowledge.
>>>>
>>>> On Tue, Aug 26, 2008 at 10:24 AM, Patrick Patterson
>>>> <[EMAIL PROTECTED]> wrote:
>>>>> Chris:
>>>>>
>>>>> On Tuesday 26 August 2008 12:58:22 Kyle Hamilton wrote:
>>>>>> There is no ExtendedKeyUsage extension.
>>>>>>
>>>>>> To fix this, in your openssl.cnf file in section [usr_cert] there is a
>>>>>> commented-out line that needs to be uncommented.
>>>>>> # keyUsage = nonRepudiation, digitalSignature, keyEncipherment
>>>>>>
>>>>>> Then generate a new certificate.
>>>>>>
>>>>> Actually - that will only set the keyUsage extension (Which you will 
>>>>> need) -
>>>>> what you also want to set is to add a line to the appropriate section in 
>>>>> the
>>>>> openssl.cnf file that you are using to generate the certificate below that
>>>>> that has:
>>>>>
>>>>> extendedKeyUsage = serverAuth,clientAuth
>>>>>
>>>>> And then regen the certificate.
>>>>>
>>>>> Have fun.
>>>>>
>>>>> Patrick.
>>>>>
>>>>>> -Kyle H
>>>>>>
>>>>>>
>>>>>> On Tue, Aug 26, 2008 at 9:20 AM, Chris Zimmerman
>>>>>>
>>>>>> <[EMAIL PROTECTED]> wrote:
>>>>>> > Here's the cert for the Watchguard:
>>>>>> >
>>>>>> > Certificate:
>>>>>> >    Data:
>>>>>> >        Version: 3 (0x2)
>>>>>> >        Serial Number: 15 (0xf)
>>>>>> >        Signature Algorithm: sha1WithRSAEncryption
>>>>>> >        Issuer: C=US, ST=TX, L=Somewhere, O=Company, OU=System,
>>>>>> > CN=Company Root CA/[EMAIL PROTECTED]
>>>>>> >        Validity
>>>>>> >            Not Before: Aug 26 16:16:57 2008 GMT
>>>>>> >            Not After : Aug 24 16:16:57 2018 GMT
>>>>>> >        Subject: C=US, ST=TX, O=Company, OU=System, CN=WG
>>>>>> >        Subject Public Key Info:
>>>>>> >            Public Key Algorithm: rsaEncryption
>>>>>> >            RSA Public Key: (1024 bit)
>>>>>> >                Modulus (1024 bit):
>>>>>> >                    00:c2:83:76:81:24:5c:48:09:71:66:bb:22:37:05:
>>>>>> >                    f3:8b:0b:f6:df:24:a0:ec:d8:65:ac:d5:77:7f:e0:
>>>>>> >                    91:f1:86:a4:00:23:17:c2:28:1f:81:e0:6d:e8:24:
>>>>>> >                    e7:0a:bb:7e:a5:72:57:6d:65:cb:ec:7c:f1:d0:64:
>>>>>> >                    63:9f:0d:0c:b3:4c:c6:e4:3f:7c:f9:1f:53:6b:c0:
>>>>>> >                    47:3a:59:4d:87:37:e5:f6:4f:ef:75:20:5b:93:0b:
>>>>>> >                    f9:8b:d7:4b:b7:4c:0c:e2:8c:2e:34:ad:23:3e:c6:
>>>>>> >                    89:1e:6f:3b:0d:52:25:69:d2:42:d3:de:cd:cd:e3:
>>>>>> >                    ef:80:8a:e0:2d:1c:20:8f:6b
>>>>>> >                Exponent: 65537 (0x10001)
>>>>>> >        X509v3 extensions:
>>>>>> >            X509v3 Basic Constraints:
>>>>>> >                CA:FALSE
>>>>>> >            Netscape Comment:
>>>>>> >                OpenSSL Generated Certificate
>>>>>> >            X509v3 Subject Key Identifier:
>>>>>> >
>>>>>> > 3E:BB:9E:11:45:7B:F7:5E:BD:1D:F9:CE:A1:A9:E1:D7:7C:71:A5:FF X509v3
>>>>>> > Authority Key Identifier:
>>>>>> >
>>>>>> > keyid:DB:E2:B6:28:36:12:83:63:B2:FA:87:E1:64:FB:44:F7:58:A0:8A:E8
>>>>>> >
>>>>>> >    Signature Algorithm: sha1WithRSAEncryption
>>>>>> >        7b:b7:d0:ca:42:96:24:6a:26:e1:a4:e1:45:91:d1:28:14:97:
>>>>>> >        e2:ea:dc:d6:59:97:73:ef:1a:5a:54:a4:33:fe:c2:0c:74:ca:
>>>>>> >        6b:e4:85:4c:a0:9d:49:7a:1a:b0:fd:48:5c:6a:bc:de:44:53:
>>>>>> >        73:23:bc:0f:ab:b6:cb:49:5a:53:2c:5c:d5:24:23:3b:e6:da:
>>>>>> >        16:22:d4:db:1c:82:ac:7a:37:01:0f:a5:4e:24:92:2b:bc:2e:
>>>>>> >        33:01:4d:5e:c3:7f:91:0f:3d:1d:ea:b8:8d:ad:38:ed:ab:44:
>>>>>> >        b7:2d:82:7b:c3:0d:2a:a2:21:8a:58:25:ac:c4:cb:f0:57:4e:
>>>>>> >        ed:ec
>>>>>> >
>>>>>> > On Tue, Aug 26, 2008 at 9:14 AM, Kyle Hamilton <[EMAIL PROTECTED]> 
>>>>>> > wrote:
>>>>>> >> openssl x509 -in [filename] -noout -text -inform PEM
>>>>>> >>
>>>>>> >> -Kyle H
>>>>>> >>
>>>>>> >> On Tue, Aug 26, 2008 at 8:44 AM, Chris Zimmerman
>>>>>> >>
>>>>>> >> <[EMAIL PROTECTED]> wrote:
>>>>>> >>> That command seems to have a syntax problem, showing: "unknown option
>>>>>> >>> [cert.pem-inserted my cert here]"
>>>>>> >>>
>>>>>> >>> On Mon, Aug 25, 2008 at 10:55 PM, Tim Hudson <[EMAIL PROTECTED]> 
>>>>>> >>> wrote:
>>>>>> >>>> Chris Zimmerman wrote:
>>>>>> >>>>> I am working to setup a Watchguard firewall with x509 certs for VPN
>>>>>> >>>>> tunnels.  I have created my own CA on my laptop and I have created 
>>>>>> >>>>> a
>>>>>> >>>>> CSR on the Watchguard product.  I have then signed the CSR with my 
>>>>>> >>>>> CA
>>>>>> >>>>> certificate successfully which then imports into the Watchguard.
>>>>>> >>>>> Here's the problem: Watchguard requires that the cert be typed as
>>>>>> >>>>> "Web" or "IPSec" if it is to be used for VPN tunnels.  Everytime I
>>>>>> >>>>> import my signed cert it shows up as a CA Cert type.  I know this 
>>>>>> >>>>> is
>>>>>> >>>>> an interop question, but has any got an idea of what to try to get
>>>>>> >>>>> this working?  I've been at this for days now with no success.
>>>>>> >>>>
>>>>>> >>>> Look a the various settings for basic constraints, key usage and
>>>>>> >>>> extended key usage as controlled in openssl.cnf ... basically you 
>>>>>> >>>> need
>>>>>> >>>> to set them to match what Watchguard wants.
>>>>>> >>>>
>>>>>> >>>> Perhaps you have the v3_ca stuff set.
>>>>>> >>>>
>>>>>> >>>> The output of
>>>>>> >>>>        openssl x509 -text -noout cert.pem
>>>>>> >>>> will let me see what you have set in the way of those extensions.
>>>>>> >>>>
>>>>>> >>>> If you have a working certificate and a non-working one then 
>>>>>> >>>> comparing
>>>>>> >>>> the text output should help show what the requirements are.
>>>>>> >>>>
>>>>>> >>>> Tim.
>>>>>> >>>
>>>>>> >>> ______________________________________________________________________
>>>>>> >>> OpenSSL Project                                 
>>>>>> >>> http://www.openssl.org
>>>>>> >>> User Support Mailing List                    
>>>>>> >>> openssl-users@openssl.org
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>>>>>> >>
>>>>>> >> ______________________________________________________________________
>>>>>> >> OpenSSL Project                                 http://www.openssl.org
>>>>>> >> User Support Mailing List                    openssl-users@openssl.org
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>>>>>> > ______________________________________________________________________
>>>>>> > OpenSSL Project                                 http://www.openssl.org
>>>>>> > User Support Mailing List                    openssl-users@openssl.org
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>>>>>>
>>>>>> ______________________________________________________________________
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>>>>>> User Support Mailing List                    openssl-users@openssl.org
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