For the most up-to-date information on Apache and SNI, including additional HTTP-Specific RFCs, please refer to the Apache Wiki
FYsI: "Multiple (different) SSL certificates on one IP" is brought to you by the magic of TLS Upgrading.
It works with newer Apache servers (2.2.x) and reasonably recent browsers (don't know versions off the top of my head).
RFC 2817 (upgrading to TLS within HTTP/1.1) has the gory details, but basically it works for a lot of people (if not the majority).
You can reproduce the old funky behavior with openssl's s_client command (or any "old enough" browser) though.
Edit to add: apparently curl can show you what's happening here better than openssl:
SSLv3
mikeg@flexo% curl -v -v -v -3 https://www.yummyskin.com
* About to connect() to www.yummyskin.com port 443 (#0)
* Trying 69.164.214.79... connected
* Connected to www.yummyskin.com (69.164.214.79) port 443 (#0)
* successfully set certificate verify locations:
* CAfile: /usr/local/share/certs/ca-root-nss.crt
CApath: none
* SSLv3, TLS handshake, Client hello (1):
* SSLv3, TLS handshake, Server hello (2):
* SSLv3, TLS handshake, CERT (11):
* SSLv3, TLS handshake, Server key exchange (12):
* SSLv3, TLS handshake, Server finished (14):
* SSLv3, TLS handshake, Client key exchange (16):
* SSLv3, TLS change cipher, Client hello (1):
* SSLv3, TLS handshake, Finished (20):
* SSLv3, TLS change cipher, Client hello (1):
* SSLv3, TLS handshake, Finished (20):
* SSL connection using DHE-RSA-AES256-SHA
* Server certificate:
* subject: serialNumber=wq8O9mhOSp9fY9JcmaJUrFNWWrANURzJ; C=CA;
O=staging.bossystem.org; OU=GT07932874;
OU=See www.rapidssl.com/resources/cps (c)10;
OU=Domain Control Validated - RapidSSL(R);
CN=staging.bossystem.org
* start date: 2010-02-03 18:53:53 GMT
* expire date: 2011-02-06 13:21:08 GMT
* SSL: certificate subject name 'staging.bossystem.org'
does not match target host name 'www.yummyskin.com'
* Closing connection #0
* SSLv3, TLS alert, Client hello (1):
curl: (51) SSL: certificate subject name 'staging.bossystem.org'
does not match target host name 'www.yummyskin.com'
TLSv1
mikeg@flexo% curl -v -v -v -1 https://www.yummyskin.com
* About to connect() to www.yummyskin.com port 443 (#0)
* Trying 69.164.214.79... connected
* Connected to www.yummyskin.com (69.164.214.79) port 443 (#0)
* successfully set certificate verify locations:
* CAfile: /usr/local/share/certs/ca-root-nss.crt
CApath: none
* SSLv3, TLS handshake, Client hello (1):
* SSLv3, TLS handshake, Server hello (2):
* SSLv3, TLS handshake, CERT (11):
* SSLv3, TLS handshake, Server key exchange (12):
* SSLv3, TLS handshake, Server finished (14):
* SSLv3, TLS handshake, Client key exchange (16):
* SSLv3, TLS change cipher, Client hello (1):
* SSLv3, TLS handshake, Finished (20):
* SSLv3, TLS change cipher, Client hello (1):
* SSLv3, TLS handshake, Finished (20):
* SSL connection using DHE-RSA-AES256-SHA
* Server certificate:
* subject: C=CA; O=www.yummyskin.com; OU=GT13670640;
OU=See www.rapidssl.com/resources/cps (c)09;
OU=Domain Control Validated - RapidSSL(R);
CN=www.yummyskin.com
* start date: 2009-04-24 15:48:15 GMT
* expire date: 2010-04-25 15:48:15 GMT
* common name: www.yummyskin.com (matched)
* issuer: C=US; O=Equifax Secure Inc.; CN=Equifax Secure Global eBusiness CA-1
* SSL certificate verify ok.
Best Answer
The SSL negotiation, including the browser analyzing the Common Name field of the certificate to compare against the host it attempted to connect to, occur long before the server has a chance to see a request. Because of this the server cannot deliver a certificate based upon the Host: head in the request. A wildcard certificate resolves this only because the same certificate is used for each hosted site.
For example if you have a *.example.com cert and you use it to host (based on Host header):
In each case the certificate is valid for the site hosted and the browser will be happy.