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multiple SSL sites on single IP/port

Author
22 Mar 2005 7:47 PM
yaponamat
Hello,

I`d appreciate help with the following scenario:

I have a Sharepoint installation, obviously on top of IIS. We generated
several sites via Sharepoint, that are accessible as third level domains:
home.ourdomain.com project1.ourdomain.com, project2.ourdomain.com etc. They
are all hosted out of one IIS server, DNS for all these domains points to IIS
server and then IIS determines which site to present to end users based on
host headers.

We would like to enable SSL on all of these sites. However, there is the
known requirement for unique ip/port combination for each secure site.
Hosting SSL on alternate ports for each site is not an option for us, so we
are faced with assigning multiple IPs to the IIS server, creating NAT entries
on the firewall for each IP, registering A records for each individual domain
and pointing them to different IPs – a lot of admin nad maintenance overhead.

Now, I read here: http://www.sitepoint.com/forums/showthread.php?t=231424
about a possible solution with using wildcard certificates:

“Another, more expensive (but reliable) alternative is to have a wildcard
ssl and offer sub-domains that share the same SSL certificate, in this
situation you do not have to buy additional IP addresses (but have to pay a
lot for these certificates)!”

We do have a wildcard certificate for our root domain *.ourdomain.com. All
the websites under IIS are using this wildcard certificate. As per proposed
solution quoted above, we should be able to skip using multiple IPs. However,
it doesn`t seem to work: if I specify default 443 port for two SSL websites
and set IP to either “default” or the primary IP of the server for both of
them, when I try to load home.ourdomain.com over SSL it does load, but then
if I try project1.ourdomain.com over SSL, it loads home.ourdomain.com content
instead. There are separate A records for home.ourdomain.com and
project1.ourdomain.com, both pointing to the same IP.

Could someone please tell if wildcard certificate solution is of any help as
claimed on this forum: http://www.sitepoint.com/forums/showthread.php?t=231424

If it does help to work around assigning multiple IPs to the IIS server,
what might I be doing wrong?

If wildcard certificate deal doesn`t help, are there any alternatives,
perhaps plugins by third parties or something like that? I`d very much like
to avoid having multiple IPs, since we may have 40 or 50 different third
level domain based websites under Sharepoint and managing all of this is a
bit of a pain.

Thanks in advance for any help.

Author
23 Mar 2005 5:42 AM
Bernard
Sharepoint is just webapp sitting on IIS, and I tested wildcard before and
it works.
Did you configure the cert in 2nd or 3rd sites as well ?

at the 2nd site property, directory security tab. can you view the
certificate ?

Show quoteHide quote
"yaponamat" <yapona***@discussions.microsoft.com> wrote in message
news:D2D37BFC-3D3A-4EC4-95C8-F9B80A143F90@microsoft.com...
> Hello,
>
> I`d appreciate help with the following scenario:
>
> I have a Sharepoint installation, obviously on top of IIS. We generated
> several sites via Sharepoint, that are accessible as third level domains:
> home.ourdomain.com project1.ourdomain.com, project2.ourdomain.com etc.
> They
> are all hosted out of one IIS server, DNS for all these domains points to
> IIS
> server and then IIS determines which site to present to end users based on
> host headers.
>
> We would like to enable SSL on all of these sites. However, there is the
> known requirement for unique ip/port combination for each secure site.
> Hosting SSL on alternate ports for each site is not an option for us, so
> we
> are faced with assigning multiple IPs to the IIS server, creating NAT
> entries
> on the firewall for each IP, registering A records for each individual
> domain
> and pointing them to different IPs – a lot of admin nad maintenance
> overhead.
>
> Now, I read here: http://www.sitepoint.com/forums/showthread.php?t=231424
> about a possible solution with using wildcard certificates:
>
> “Another, more expensive (but reliable) alternative is to have a
> wildcard
> ssl and offer sub-domains that share the same SSL certificate, in this
> situation you do not have to buy additional IP addresses (but have to pay
> a
> lot for these certificates)!”
>
> We do have a wildcard certificate for our root domain *.ourdomain.com. All
> the websites under IIS are using this wildcard certificate. As per
> proposed
> solution quoted above, we should be able to skip using multiple IPs.
> However,
> it doesn`t seem to work: if I specify default 443 port for two SSL
> websites
> and set IP to either “default” or the primary IP of the server for
> both of
> them, when I try to load home.ourdomain.com over SSL it does load, but
> then
> if I try project1.ourdomain.com over SSL, it loads home.ourdomain.com
> content
> instead. There are separate A records for home.ourdomain.com and
> project1.ourdomain.com, both pointing to the same IP.
>
> Could someone please tell if wildcard certificate solution is of any help
> as
> claimed on this forum:
> http://www.sitepoint.com/forums/showthread.php?t=231424
>
> If it does help to work around assigning multiple IPs to the IIS server,
> what might I be doing wrong?
>
> If wildcard certificate deal doesn`t help, are there any alternatives,
> perhaps plugins by third parties or something like that? I`d very much
> like
> to avoid having multiple IPs, since we may have 40 or 50 different third
> level domain based websites under Sharepoint and managing all of this is a
> bit of a pain.
>
> Thanks in advance for any help.
>
Author
23 Mar 2005 9:03 PM
yaponamat
Bernard,

thanks for your reply. yes, the cert is configured for all websites and I
can view it under 2nd or 3rd site`s directory security.

However, the stuff doesn`t work on single ip/port combination. it would load
one site`s content only. here`s a good explanation of the process I found in
this newsgroup:

---------------------------------------------------------
Here's a quick description, to demonstrate why:

1. The client takes the URL and resolves the name into an IP address, and a
port (usually a default port).
2. The client connects to that IP address, on the requested port
3. The server running at that IP address and port answers.
4. The client sends a "hello" message, asking the server to send its
certificate.
5. The server sends the certificate to the client.
6. The client checks the name in the certificate against the name it had in
step 1.
7.1. If the certificate matches, the client and server start encrypted
exchanges.
7.2. If the certificate doesn't match, the client displays an error to the
user and stops.
8. The client sends HTTP request headers, encrypted, to the server.
9. The server sends back HTTP responses, encrypted, containing content
requested.

Note that host headers are sent in step 8, but the server has to pick a
certificate to send in step 5, and that certificate must have the server
name that the user asked for.  The server has no clue as to which
certificate it must pick, so it must have a single certificate to send back
on that IP address and port.

There is work under way to produce a "next version" of TLS, that will allow
a client to send the host name it wants in step 4, so that the server can
choose among several certificates, but it is not clear exactly when (if
ever) this will be implemented in browsers or web servers - and it has to be
implemented, and enabled, in both if it is to work. ----------------------------------------------------------------------------------------

I`m still curious whether it`s possible to get it to work with wildcard
certificate...


Show quoteHide quote
"Bernard" wrote:

> Sharepoint is just webapp sitting on IIS, and I tested wildcard before and
> it works.
> Did you configure the cert in 2nd or 3rd sites as well ?
>
> at the 2nd site property, directory security tab. can you view the
> certificate ?
>
> --
> Regards,
> Bernard Cheah
> http://www.tryiis.com/
> http://support.microsoft.com/
> http://www.msmvps.com/bernard/
>
>
> "yaponamat" <yapona***@discussions.microsoft.com> wrote in message
> news:D2D37BFC-3D3A-4EC4-95C8-F9B80A143F90@microsoft.com...
> > Hello,
> >
> > I`d appreciate help with the following scenario:
> >
> > I have a Sharepoint installation, obviously on top of IIS. We generated
> > several sites via Sharepoint, that are accessible as third level domains:
> > home.ourdomain.com project1.ourdomain.com, project2.ourdomain.com etc.
> > They
> > are all hosted out of one IIS server, DNS for all these domains points to
> > IIS
> > server and then IIS determines which site to present to end users based on
> > host headers.
> >
> > We would like to enable SSL on all of these sites. However, there is the
> > known requirement for unique ip/port combination for each secure site.
> > Hosting SSL on alternate ports for each site is not an option for us, so
> > we
> > are faced with assigning multiple IPs to the IIS server, creating NAT
> > entries
> > on the firewall for each IP, registering A records for each individual
> > domain
> > and pointing them to different IPs – a lot of admin nad maintenance
> > overhead.
> >
> > Now, I read here: http://www.sitepoint.com/forums/showthread.php?t=231424
> > about a possible solution with using wildcard certificates:
> >
> > “Another, more expensive (but reliable) alternative is to have a
> > wildcard
> > ssl and offer sub-domains that share the same SSL certificate, in this
> > situation you do not have to buy additional IP addresses (but have to pay
> > a
> > lot for these certificates)!”
> >
> > We do have a wildcard certificate for our root domain *.ourdomain.com. All
> > the websites under IIS are using this wildcard certificate. As per
> > proposed
> > solution quoted above, we should be able to skip using multiple IPs.
> > However,
> > it doesn`t seem to work: if I specify default 443 port for two SSL
> > websites
> > and set IP to either “default” or the primary IP of the server for
> > both of
> > them, when I try to load home.ourdomain.com over SSL it does load, but
> > then
> > if I try project1.ourdomain.com over SSL, it loads home.ourdomain.com
> > content
> > instead. There are separate A records for home.ourdomain.com and
> > project1.ourdomain.com, both pointing to the same IP.
> >
> > Could someone please tell if wildcard certificate solution is of any help
> > as
> > claimed on this forum:
> > http://www.sitepoint.com/forums/showthread.php?t=231424
> >
> > If it does help to work around assigning multiple IPs to the IIS server,
> > what might I be doing wrong?
> >
> > If wildcard certificate deal doesn`t help, are there any alternatives,
> > perhaps plugins by third parties or something like that? I`d very much
> > like
> > to avoid having multiple IPs, since we may have 40 or 50 different third
> > level domain based websites under Sharepoint and managing all of this is a
> > bit of a pain.
> >
> > Thanks in advance for any help.
> >
>
>
>
Author
24 Mar 2005 2:45 AM
Bernard
Yes, from your description because the host header detail is encrypted,
hence SSL will not click with host header, there's a new RFC spec which
support host header with SSL, I don't have the rfc number now.

Anyway - I tested this years ago. what you can do is:
-setup each site with the same ip/port + different host header a.bla.com,
b.bla.com, etc
-make sure cert is associate with each site
-make sure port 443 is assign in each site
-do a netstat -ano, and make sure port 443 is binding to the IP.

then browse https://a.bla.com/  https://b.bla.com/

why this would work because, when you refer to https://b.bla.com/ it is
actually using the cert copy at site 1 (a.bla.com), and since the common
name is *.bla.com, you will not get the cert alert prompt.

Show quoteHide quote
"yaponamat" <yapona***@discussions.microsoft.com> wrote in message
news:22EC8BEA-889D-4619-807F-FAB5EF46FA22@microsoft.com...
> Bernard,
>
> thanks for your reply. yes, the cert is configured for all websites and I
> can view it under 2nd or 3rd site`s directory security.
>
> However, the stuff doesn`t work on single ip/port combination. it would
> load
> one site`s content only. here`s a good explanation of the process I found
> in
> this newsgroup:
>
> ---------------------------------------------------------
> Here's a quick description, to demonstrate why:
>
> 1. The client takes the URL and resolves the name into an IP address, and
> a
> port (usually a default port).
> 2. The client connects to that IP address, on the requested port
> 3. The server running at that IP address and port answers.
> 4. The client sends a "hello" message, asking the server to send its
> certificate.
> 5. The server sends the certificate to the client.
> 6. The client checks the name in the certificate against the name it had
> in
> step 1.
> 7.1. If the certificate matches, the client and server start encrypted
> exchanges.
> 7.2. If the certificate doesn't match, the client displays an error to the
> user and stops.
> 8. The client sends HTTP request headers, encrypted, to the server.
> 9. The server sends back HTTP responses, encrypted, containing content
> requested.
>
> Note that host headers are sent in step 8, but the server has to pick a
> certificate to send in step 5, and that certificate must have the server
> name that the user asked for.  The server has no clue as to which
> certificate it must pick, so it must have a single certificate to send
> back
> on that IP address and port.
>
> There is work under way to produce a "next version" of TLS, that will
> allow
> a client to send the host name it wants in step 4, so that the server can
> choose among several certificates, but it is not clear exactly when (if
> ever) this will be implemented in browsers or web servers - and it has to
> be
> implemented, and enabled, in both if it is to work.
> ----------------------------------------------------------------------------------------
>
> I`m still curious whether it`s possible to get it to work with wildcard
> certificate...
>
>
> "Bernard" wrote:
>
>> Sharepoint is just webapp sitting on IIS, and I tested wildcard before
>> and
>> it works.
>> Did you configure the cert in 2nd or 3rd sites as well ?
>>
>> at the 2nd site property, directory security tab. can you view the
>> certificate ?
>>
>> --
>> Regards,
>> Bernard Cheah
>> http://www.tryiis.com/
>> http://support.microsoft.com/
>> http://www.msmvps.com/bernard/
>>
>>
>> "yaponamat" <yapona***@discussions.microsoft.com> wrote in message
>> news:D2D37BFC-3D3A-4EC4-95C8-F9B80A143F90@microsoft.com...
>> > Hello,
>> >
>> > I`d appreciate help with the following scenario:
>> >
>> > I have a Sharepoint installation, obviously on top of IIS. We generated
>> > several sites via Sharepoint, that are accessible as third level
>> > domains:
>> > home.ourdomain.com project1.ourdomain.com, project2.ourdomain.com etc.
>> > They
>> > are all hosted out of one IIS server, DNS for all these domains points
>> > to
>> > IIS
>> > server and then IIS determines which site to present to end users based
>> > on
>> > host headers.
>> >
>> > We would like to enable SSL on all of these sites. However, there is
>> > the
>> > known requirement for unique ip/port combination for each secure site.
>> > Hosting SSL on alternate ports for each site is not an option for us,
>> > so
>> > we
>> > are faced with assigning multiple IPs to the IIS server, creating NAT
>> > entries
>> > on the firewall for each IP, registering A records for each individual
>> > domain
>> > and pointing them to different IPs – a lot of admin nad
>> > maintenance
>> > overhead.
>> >
>> > Now, I read here:
>> > http://www.sitepoint.com/forums/showthread.php?t=231424
>> > about a possible solution with using wildcard certificates:
>> >
>> > “Another, more expensive (but reliable) alternative is to have a
>> > wildcard
>> > ssl and offer sub-domains that share the same SSL certificate, in this
>> > situation you do not have to buy additional IP addresses (but have to
>> > pay
>> > a
>> > lot for these certificates)!”
>> >
>> > We do have a wildcard certificate for our root domain *.ourdomain.com.
>> > All
>> > the websites under IIS are using this wildcard certificate. As per
>> > proposed
>> > solution quoted above, we should be able to skip using multiple IPs.
>> > However,
>> > it doesn`t seem to work: if I specify default 443 port for two SSL
>> > websites
>> > and set IP to either “default” or the primary IP of the
>> > server for
>> > both of
>> > them, when I try to load home.ourdomain.com over SSL it does load, but
>> > then
>> > if I try project1.ourdomain.com over SSL, it loads home.ourdomain.com
>> > content
>> > instead. There are separate A records for home.ourdomain.com and
>> > project1.ourdomain.com, both pointing to the same IP.
>> >
>> > Could someone please tell if wildcard certificate solution is of any
>> > help
>> > as
>> > claimed on this forum:
>> > http://www.sitepoint.com/forums/showthread.php?t=231424
>> >
>> > If it does help to work around assigning multiple IPs to the IIS
>> > server,
>> > what might I be doing wrong?
>> >
>> > If wildcard certificate deal doesn`t help, are there any alternatives,
>> > perhaps plugins by third parties or something like that? I`d very much
>> > like
>> > to avoid having multiple IPs, since we may have 40 or 50 different
>> > third
>> > level domain based websites under Sharepoint and managing all of this
>> > is a
>> > bit of a pain.
>> >
>> > Thanks in advance for any help.
>> >
>>
>>
>>