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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>>>>> ______________________________________________________________________
>>>>> OpenSSL Project                                 http://www.openssl.org
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