I have this same issue and posted to the list in November about it. Joe 
responded with:

On Nov 4, 2014, at 11:02 AM, Joe Gooch <[email protected]> wrote:

> Pound 2.6 does not include support for SAN attributes on secondary 
> certificates.  You would need to run 2.7 for that feature.
> 
> Joe

I'm not sure if this could be changed if there was enough interest, but it 
would certainly help me when my certificates come up for renewal since right 
now I have to buy extra ones because of this.

-T

On Dec 15, 2014, at 8:20 AM, qutic development <[email protected]> wrote:

> Hi,
> 
> I am using Pound v2.6 with Joe Goochs pcidss branch and SNI with multiple 
> certificates on one IP. This works fine with SHA-Certs, but today I tried to 
> include a new SHA256-certificate which failed - only the first cert in the 
> list is used, but not the right one for the domain.
> 
> Next I changed all certificates from SHA to the new SHA256 ones, but this 
> failed too - only the first cert in the list is used, but not the right one 
> for the domain.
> 
> Is this a known issue? Any ideas how to fix it?
> 
> Best regards
> Stefan
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