I am having the same problem with apis.live.net:443. I am running Debian
stable with ca-certificates 20141019+deb8u1.

Thanks.
-nandhp

$ openssl s_client -connect apis.live.net:443
CONNECTED(00000003)
depth=2 C = IE, O = Baltimore, OU = CyberTrust, CN = Baltimore
CyberTrust Root
verify error:num=20:unable to get local issuer certificate
verify return:0
---
Certificate chain
 0 s:/C=US/ST=WA/L=Redmond/O=Microsoft Corporation/OU=Microsoft
Corporation/CN=storage.live.com
   i:/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/OU=Microsoft
IT/CN=Microsoft IT SSL SHA2
 1 s:/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/OU=Microsoft
IT/CN=Microsoft IT SSL SHA2
   i:/C=IE/O=Baltimore/OU=CyberTrust/CN=Baltimore CyberTrust Root
 2 s:/C=IE/O=Baltimore/OU=CyberTrust/CN=Baltimore CyberTrust Root
   i:/C=US/O=GTE Corporation/OU=GTE CyberTrust Solutions, Inc./CN=GTE
CyberTrust Global Root
---
Server certificate
[...]
subject=/C=US/ST=WA/L=Redmond/O=Microsoft Corporation/OU=Microsoft
Corporation/CN=storage.live.com
issuer=/C=US/ST=Washington/L=Redmond/O=Microsoft
Corporation/OU=Microsoft IT/CN=Microsoft IT SSL SHA2
---
No client certificate CA names sent
---
SSL handshake has read 6828 bytes and written 509 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-AES256-SHA384
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : ECDHE-RSA-AES256-SHA384
    Session-ID: [...]
    Session-ID-ctx:
    Master-Key: [...]
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1454865834
    Timeout   : 300 (sec)
    Verify return code: 20 (unable to get local issuer certificate)
---
^C

On Thu, 28 Jan 2016 16:44:09 +0100 Peter Dahlberg <catd...@tuxzone.org>
wrote:
> Hi,
> 
> There seems to be a similar looking issue because of the removed "GTE 
> CyberTrust Global Root".
> 
> jessie:
> 
> $ openssl s_client -connect pictureis24-a.akamaihd.net:443
> CONNECTED(00000003)
> depth=2 C = IE, O = Baltimore, OU = CyberTrust, CN = Baltimore CyberTrust Root
> verify error:num=20:unable to get local issuer certificate
> verify return:0
> ---
> Certificate chain
>  0 s:/C=US/ST=MA/L=Cambridge/O=Akamai Technologies Inc./CN=a248.e.akamai.net
>    i:/C=NL/L=Amsterdam/O=Verizon Enterprise 
> Solutions/OU=Cybertrust/CN=Verizon 
> Akamai SureServer CA G14-SHA2
>  1 s:/C=NL/L=Amsterdam/O=Verizon Enterprise 
> Solutions/OU=Cybertrust/CN=Verizon 
> Akamai SureServer CA G14-SHA2
>    i:/C=IE/O=Baltimore/OU=CyberTrust/CN=Baltimore CyberTrust Root
>  2 s:/C=IE/O=Baltimore/OU=CyberTrust/CN=Baltimore CyberTrust Root
>    i:/C=US/O=GTE Corporation/OU=GTE CyberTrust Solutions, Inc./CN=GTE 
> CyberTrust Global Root
> ---
> 
> testing:
> 
>  % openssl s_client -connect pictureis24-a.akamaihd.net:443
> CONNECTED(00000003)
> depth=2 C = IE, O = Baltimore, OU = CyberTrust, CN = Baltimore CyberTrust Root
> verify return:1
> depth=1 C = NL, L = Amsterdam, O = Verizon Enterprise Solutions, OU = 
> Cybertrust, CN = Verizon Akamai SureServer CA G14-SHA2
> verify return:1
> depth=0 C = US, ST = MA, L = Cambridge, O = Akamai Technologies Inc., CN = 
> a248.e.akamai.net
> verify return:1
> ---
> Certificate chain
>  0 s:/C=US/ST=MA/L=Cambridge/O=Akamai Technologies Inc./CN=a248.e.akamai.net
>    i:/C=NL/L=Amsterdam/O=Verizon Enterprise 
> Solutions/OU=Cybertrust/CN=Verizon 
> Akamai SureServer CA G14-SHA2
>  1 s:/C=NL/L=Amsterdam/O=Verizon Enterprise 
> Solutions/OU=Cybertrust/CN=Verizon 
> Akamai SureServer CA G14-SHA2
>    i:/C=IE/O=Baltimore/OU=CyberTrust/CN=Baltimore CyberTrust Root
>  2 s:/C=IE/O=Baltimore/OU=CyberTrust/CN=Baltimore CyberTrust Root
>    i:/C=US/O=GTE Corporation/OU=GTE CyberTrust Solutions, Inc./CN=GTE 
> CyberTrust Global Root
> ---
> 
> Kind regards,
> Peter
> 
> 
> 

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