As per comments by Viktor on the dev list, this is by design:
On 27 April 2014 17:10, Viktor Dukhovni <openssl-us...@dukhovni.org> wrote:
> On Sun, Apr 27, 2014 at 01:04:13PM +0200, sch_m via RT wrote:
>
>> I was playing around with openssl and found a minor bug which
>> makes possible to put the end date before the start date. This
>> happend by creating a certificate using
>
> I think this is a feature, not a bug. It should be possible to
> create a certificate that is never valid. It will be accepted only
> by clients that directly trust the public key or certificate
> fingerprint and ignore the dates.
>
> Also, generating such certificates makes it easier to generate test
> cases for verifier implementations. I've used "-days -1" from time
> to time to generate such "never valid" certificates.
>
> --
> Viktor.

Matt

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