lync certificate planning and assignments

© 2013 - Thomas Pött, Microsoft MVP LYNC

Lync Certificate Planning and Assignments (Edge, Reverse Proxy, Director, Frontend, Mediation, WAC)

Copyright© and written 2013 by Thomas Pött, MVP Lync/ Unified Communication

Blog: http://lyncuc.blogspot.de/2013/02/demystify-lync-enterprise-voice-phone.html

Email: [email protected]

1 About the Author:

Thomas Pött, Microsoft MVP LYNC and MCITP Lync

Extensive experience in business and market development. Specialized in intercultural and business

relationship in Asia. Successful in providing leadership on new topics and complex global projects that require

interfacing with internal/external teams and ecosystems. Early adaptor of visionary technologies.

• 20+ year career within different companies in the areas software development, telecommunication, IT,

mobility and hosted/cloud services.

• Strong technical and business background – was member of Microsoft´s German Inner Circle.

• Organized, logical, rationale thinker and problem solver with superb communication and collaboration

skills.

• Business Management skill in strategic and organized developing German SME subsidiaries in Asia

Specialties: Management:

Start up companies, Business Relation Management, Partner Relation Management, Enterprise Business

Sales Skills, strong team leader and motivator, perfect Asian business and human behavior understandings,

excellent financial cash flow management

Technical:

Microsoft Office 365, Public and Private Cloud Computing, specialized in Hybrid Cloud integration, Unified

Communication (LYNC, OCS, Exchange), Security (PKI, ForeFront), Active Directory, German efficiency in

consulting

I’m living in Bad Wiessee, Germany near Munich and work for ACP IT Solutions AG. Beside the technical

interests, I enjoy paragliding and para-motor.

This article will part of my new book I’m working on, since Lync Enterprise Voice is a more and more complex

environment, where it’s difficult to get the right information.

Any suggestion what areas of EV are from interest, I would be glad to be inspired.

http://lyncuc.blogspot.de/2013/02/demystify-lync-enterprise-voice-phone.html


The following article is optimized for Lync 2013, but in general valid for Lync 2010 or OCS 2007

NOTE:

First I need to highlight to you is a topic, I’m always ask for support. Lync Server and Client make use of

Certificates, therefor the technical principals of certificate deployments are necessary to understand. If

on your Clients or Servers an Internet Explorer Setting with a Proxy Server is activated, make sure you

have the correct design. The CRL (Certificate Revocation List) check is mostly HTTP based (in AD

Environments also possible via FILE or LDAP), if you have setup an internal Proxy, which cannot redirect

the request into your LAN, you will run into major issues!

I wrote another article in 2012 which maybe from interest for you too:

Forefront TMG – Directors, Front End and Standard Edition for Lync

http://lyncuc.blogspot.de/2012/07/forefront-tmg-directors-fe-and-se-for.html


2 GENERAL

Lync Certificate Planning must be separated into three different areas:

1. INTERNAL Deployment

(all internally deployed Lync Servers, e.g. Frontend, Directors, Mediation,..)

- Including the internal NIC of the EDGE Server

2. EXTERNAL Deployment

2.1. Edge Server

2.2. Reverse Proxy

Indirectly there is a fourth area, this is if you have Pool Server configuration, due the Virtual Service

configured on the Load Balancer. But I will explain this in detail within another blog later.

All Lync Server have one requirement in common, this is the way how they accept authentication based

on TLS. Accepting the trust, Lync Server need a matching between the certificates common name and it

FQDN. The server or client, initiating the communication with the certificate holder use DNS lookup to

refer to this server FQDN. If this reference does not match the common name of the certificate, the

authentication will fail.

The common name, notated as CN in X.500 terminology, is what is referenced and must match the DNS

record for the server’s FQDN. For details about the specific format http://www.ietf.org/rfc/rfc3280.txt.

This explains why a dedicated wildcard certificate would not work in Lync Server, because the common

name must match exactly to the FQDN of the A record defined for the referenced server or pool. The

DNS A record and the certificate subject name/common name (SN/CN) is also referenced to the trusted

server list in Active Directory service Global or Configuration settings.

Reference: Microsoft Technet Certificate Guide

Important: You cannot use a wildcard CN/SN (for example, *.contoso.com) when you configure

certificates for Office Communications Server 2007 R2 and Office Communications Server 2007

(now Lync). If you do so, they will not operate as expected and the problem is very difficult to

diagnose. You can use wildcard entries in the subject alternative name, but the common name is

specific. Specific issues include the inability to start services because the trusted services in

Active Directory Domain Services (AD DS) and the SN and CN do not match, mutual

authentication fails, and so on.

http://www.ietf.org/rfc/rfc3280.txt


Note at last:

And, as mentioned earlier, public CAs and your internal CA can create wildcard SN/CN certificates, but

they are neither reliable nor supported. It is recommended that you do this right the first time and avoid

the potential for serious issues in the future by not trying to use a certificate that uses a wildcard SN/CN,

such as *.domain.com, to define the three Edge Server services.


3 Server Components

(Certificates are requited)

3.1 INTERNAL Deployment:

Standard Edition Front End Pool Server

This server is the consolidated “all-in-one” Server and requires an internal certificate.

Enterprise Edition Front End Pools

This server is the High-Available Lync Core Component. Beside the local servers themselves, they also

provide the consolidated access names and are attached with a Load Balancer. The certificate must

contain the Pool and Server name. In certain circumstance it makes sense haven a generic certificate,

which contains all Pool Server Names and the Pool Name (SAN certificate).

Director Pools

This server is the “Authentication and Redirection” server. In lager deployment, with multiple site, you

need the Director to offload authentication traffic and redirect the user to the homed pool.

Mediation Pools

This server is responsible for Media Conversion

Persistent Chat Pools

This server handles the “Group Chats”

Trusted Application Server

All Server, which need to be trusted by Lync have to be publish that Lync is aware of them. If A

certificate is required if the trusted server will us TLS.

PSTN Gateway


The PSTN Gateway object, might be a Lync Gateway, Gateway card or an SIP Trunk. With the PSTN

Gateway, this depends on how the setup must or can be done. If you make use of a TLS connection, e.g.

to an ISDN card, you will need a certificate stored on the PSTN gateway.

Office Web Apps Server

The WAC/ OWA server requires a certificate, this is OAuth ready.

NOTE:

As described in the section for Front End Pool Server, generally it has to be part of the planning how

certificates are requested if a Load Balancer is involved. A Load Balancer can be setup in different way

(in-band or out-band), this will discussed in a separate blog. But you need to remember, the Load

Balancer is the central point for the IP connection, therefor it needs the FQDN of the POOL in its

certificate presenting to the connecting client. Depending on how the Load Balancer is established, you

will than understand why the Pool Member Server needs beside the Pool FQDN also its local FQDN in its

local certificate!

3.2 EXTERNAL Deployment:

Edge Pools

The Edge Server is the main component used to communicate from and with outside of the

organization. (Responsible for PIC, XMPP, Federation, remote access and Web Conferencing)

Edge Pools have one specialty, for best practice and security reason, they make us of 2 NICs, an internal

and external.

Note:

Edge Server need to have 2x NIC with different subnet, need the primary internal DNS Suffix set, must not

be a domain member and will need to certificate, and internal CA issued certificate for the internal

directed interface and an official, public certificate (where I will take more later about). Additionally,

remember to set the default gateway on the external facing NIC and all internal subnet must be assigned

a static route based on the internal facing NIC.

Reverse Proxy

This optional component only needs an external certificate and it’s responsible for Web-Based Services,

e.g. Address Book or Dailin Conferencing page.


4 Topologies

Topology represents your entire corporate Lync Server deployment and all involved Lync Systems, with

one exception, the Reverse Proxy. Since we want to define the necessary certificates, it is necessary to

fully understand the topology and server function which then represents the service making use of.

4.1 Internet facing Systems

Before we actually start with the topologies, we need a clarification what the external facing system will

do, what they are responsible for and what not.

Else which kind of usability scenarios do we have?

Remote Users

Federated User

Public Instant Messaging Connectivity Users

Mobile Users

And the type of communication:

IM

Presence

Audio/ Video/ App Sharing

Web Conferencing

A/V Conferencing

4.1.1 Edge Server:

The Edge Server, the Internet facing system responsible for enabling users to communicate with

external partners, connect remotely and establish connectivity with Public IM Services, like Live or

Skype.

Also the Audio/ Video and App Sharing runs through the Edge server if a Meeting is in place.

One newer component, called XMPP (Extensible Messaging and Presence Protocol), is established in

Edge Server since Lync 2013, it is used for partner federation e.g. Google Talk.

Edge Server is not responsible for any other service as the described services in this section.

4.1.2 Reverse Proxy:

Reverse Proxy as an optional, not Lync Server Topology component, becomes responsible for several

areas and will publish internal resources.

It can be separated into two areas, the remote user connectivity and generally spoke “meeting’s”.


Remote User:

Remote user need to connect to Lync server internal service, called “Web Service”, they are responsible

for Address Book Synchronization, Distribution List Expansion, Device Updates, Mobility Services.

Meetings:

Access to Meetings, Conference Join Locations (PSTN Dial-In Numbers), Access to personal Dial-In and

PIN information, Download Meeting Content.

4.2 Topology and certificate assignment

In sum we will have one primary and two secondary SIP Domains in our example topologies defined.

The third deployment would be a very complex scenario, where we have multiple geographically

deployed Edge Server/ Reverse Proxy scenario.

I’m not having a look into Enterprise Voice, it is not required since we want to understand the certificate

design.

Our deployed domains are:

Active Directory Domain: INTERNAL.AD

SIP PRIMARY DOMAIN: DOMAIN.COM

SIP Secondary Domain: DOMAIN-A.COM and DOMAIN-B.COM

In general, what we have to remember for Lync Topology designs and the related certificates is:

1. On Edge Server, Wildcard Certificates are not allowed

2. On Edge Server we need matching CN and 1st SAN entry of access FQDN, e.g. SIP.DOMAIN.COM

3. On Edge Server we need SAN entries for AV and WebConferencing

4. On Reverse Proxy, we need a matching CN with the associated Director Pool external Web

Service FQDN

5. On Reverse Proxy, all external Web Service FQDN must be in SAN

6. On Reverse Proxy all other FQDN can be consolidated in a Wildcard entry


4.2.1 SIMPLE TOPOLOGY

The “SIMPLE TOPOLOGY” is the most common deployment for smaller customers. High availability is

mostly not required by Lync due to virtualization. For those customers, VM Host availability and

snapshots are sufficient enough.

The simple deployment includes the full feature set of Lync in direction to the internet. This includes

login possibility for all Lync Clients, incl. App Store and Mobile clients. Federation is also handled.

LAN DMZ INTERNET

Office Web Apps

PKI internal

Lync Front End

Lync Edge

Reverse Proxy

Public CACommon Name:edge.internal.ad

Common Name:sip.internal.ad

SAN*:fe01.internal.adsip.(alldomains)lyncdiscoverinternal.(alldomains)dialin.domain.commeet.domain.com

Common Name:wac01.internal.ad

Common Name:sip.domain.com

SAN:sip.domain.comsip.domain-a.comsip.domain-b.comwebconf.domain.com

Common Name:webext.domain.com

SAN:webext.domain.com*.domain.com*.domain-a.com*.domain-b.com

Listener01:To Lync Front End

Listener02:To Office Web Apps

SIMPLE TOPOLOGY

*) if you what establish multiple domain based simple URL, all of them must be included in the SAN.You also have the opportunity creating the same wildcard + SAN mixture certificate.


4.2.2 COMPLEX TOPOLOGY

The “COMPLEX TOPOLOGY” is the most common deployment for lager, multi pool customers. High

availability is required for Lync and due to multi pool deployments, login traffic must be handled by

Director Servers.

This deployment includes the full feature set of Lync in direction to the internet. This includes login

possibility for all Lync Clients, incl. App Store and Mobile clients. Federation is also handled.

LAN DMZ INTERNET

Office Web AppsPKI internal

Lync Front EndPool02

Lync Edge Pool

Reverse Proxy

Public CACommon Name:edge.internal.ad

SAN:edge.internal.adedge11.internal.adedge12.internal.ad

Common Name:pool02.internal.ad

SAN*:pool02.internal.adfe21.internal.adfe22.internal.adweb02ext.domain.comdialin.domain.commeet.domain.com



SAN:sip.domain.comsip.domain-a.comsip.domain-b.comav.domain.comwebconf.domain.com

Common Name:webext.domain.com

SAN:webdirext.domain.comweb01ext.domain.comweb02ext.domain.com*.domain.com*.domain-a.com*.domain-b.com

Listener01:To Lync FE Pool01


COMPLEX TOPOLOGY

Lync Director Pool





SAN*:sip.domain.comdir11.internal.addir12.internal.adwebdirext.domain.commeet.domain.comdialin.domain.comlyncdiscoverinternal.(alldomains)


Listener03:To Director Pool, simple URL, mobility and its WebService

SIP.alldomains+ Simple URL+ Mobility+ WebService

*) if you want to establish multiple domain based simple URL, all of them must be included in the SAN.You also have the opportunity creating the same wildcard + SAN mixture certificate.Wildcard is supported for simple URL only


4.2.3 GEOGRAPHICALLY deployed COMPLEX TOPOLOGY

The “GEOGRPHICALLY COMPLEX TOPOLOGY” is the most complex deployment for international

customers. High availability is required for Lync this is also extended into a multi-region Edge Access

scenario.

This deployment includes the fully feature set of Lync in direction to the internet. This includes login

possibility for all Lync Clients, incl. App Store and Mobile clients. Federation is also handled.

The main component for geographically distributed deployments is the GEO-Load Balancer. It handles

the Internet based distribution for Edge Access.

Since I’m talking about Certificates, it is important to understand the Certificates distribution.


DMZ

Lync Edge PoolGERMANY

Reverse ProxyGERMANY







LAN DMZ INTERNET

Office Web Apps

PKI internal

Lync Edge PoolUSA

Reverse ProxyUSA

Public CA




Common Name:webdirUSext.domain.com

SAN:webdirUSext.domain.comwebdirGERext.domain.comweb01ext.domain.comweb02ext.domain.com*.domain.com*.domain-a.com*.domain-b.com



GEORGRAPHICALLY deployed COMPLEX TOPOLOGY

Lync Director Pool USA





SAN*:sip.domain.comdir11.internal.addir12.internal.adwebdirUSext.domain.commeet.domain.comdialin.domain.comlyncdiscoverinternal.(alldomains)




*) if you want to establish multiple domain based simple URL, all of them must be included in the SAN.You also have the opportunity creating the same wildcard + SAN mixture certificate.Wildcard is supported for simple URL only




Lync Director Pool GERMANY


SAN*:sip.domain.comdir11.internal.addir12.internal.adwebdirGERext.domain.commeet.domain.comdialin.domain.comlyncdiscoverinternal.(alldomains)


Office Web Apps


Datacenter US

Datacenter GERMANY

Common Name:webdirGERext.domain.com

SAN:webdirUSext.domain.comwebdirGERext.domain.comweb01ext.domain.comweb02ext.domain.com*.domain.com*.domain-a.com*.domain-b.com

e.g. KEMP GEO LOADMASTERDeployed in three region, US, GERMANY and SINGAPORE.DNS Queries will be redirected to any of this GEO LOAD MASTER. Based on the Clients location, the nearest LYNC EDGE Server Site will be chosen.

Internally, you have two choises:1.) user two independen DNS Server Zones2.) use a GEO Load Balancer for your internal deployment

Common Name:edgeUSA.internal.ad

SAN:edgeUSA.internal.adedge11.internal.adedge12.internal.ad

Common Name:edgeGER.internal.ad

SAN:edgeGER.internal.adedge21.internal.adedge22.internal.ad


5 Certificate Template Table

Making it easier for you, I prefilled in the Template with this configuration example:

We have 3 SIP domains in our deployment 1x Enterprise Pool, plus 1x Standard Edition Server in a

branch. I also have 1x Director installed.

5.1 EDGE SERVER

Type Configuration Comment

Common Name sip.domain.com Primary SIP domain

SAN sip.domain.com First SAN entry must repeat the primary SIP domain

SAN wc.domain.com Web Conferencing only for the named primary SIP domain needed

SAN xmpp.domain.com XMPP Federation (if installed) of primary SIP domain

SAN sip.DOMAIN-A.com Second SIP domain

SAN sip.DOMAIN-B.com Third SIP domain

Table 1 Edge Server external Certificate

5.2 REVERSE PROXY SERVER


Common Name extweb01.domain.com Just a Common Name

SAN extdir01.domain.com External URL of Director Server. Must be primary SIP domain

SAN extweb01.domain.com External URL of Enterprise Pool Server. Must be primary SIP domain

SAN extweb02.domain.com External URL of Standard Server. Must be primary SIP domain

SAN *.DOMAIN-A.com

SAN *.DOMAIN-B.com

Table 2 Reverse Proxy Server external Certificate

5.3 HYBRID CERTIFICATE (SUMMARY)


Common Name sip.domain.com Primary SIP domain


SAN sip.domain.com

SAN wc.domain.com

SAN xmpp.domain.com

SAN sip.DOMAIN-A.com

SAN sip.DOMAIN-B.com

SAN extdir01.domain.com

SAN extweb01.domain.com

SAN extweb02.domain.com

SAN *.DOMAIN-A.com This is the Wildcard part for Revers Proxy of DOMAIN-A.com

SAN *.DOMAIN-B.com This is the Wildcard part for Revers Proxy of DOMAIN-B.com

Table 3 Consolidated, public Certificate

6 Certificate Request Generation

How do I request the Wildcard+SAN certificate?

The following demonstration explains hybrid certificate request in Lync. This has to be done on the Edge

Server itself. You have to login to the Edge Server and start the Bootstripper, than you chose the

“Request, Install and Assign Certificates”.

In this example, I’m using three domains:

PRIMAY SIP Domain: cie.acp.de

SECONDARY SIP Domains: domain.com and domain.com


Since this will be our Hybrid Certificate, there is still one point we haven’t spoken about. How do we

request this certificate? If you for example initiate the request with DigiCert, you need to buy three (3)

wildcard certificates first, than you process with DigiCert manually via email.

So remember you might take one/ two days longer in placing the order.


We need to prepare a CSR file for external, manual requests:


The friendly name can is only for better identification of the certificate in the store:


The first defined SN'S are provided by Lync automatically:

Next, you need to include the addressed SIP domains configured in Lync Topology builder:

As discussed, here we come to the point, where we need to add additional SAN entries as

explained and defined the table earlier:


Verify the correct CN and SAN entries:


Finally you defined the Certificate Request. This is your CSR file. Provide this information to

your Certificate supplier.

Note:

Remember, the Certificate File you will receive will NOT contain the PRIVATE KEY. The Private Key will be generate once you apply this certificate on the Edge Server where you generated the statement !


Only after its process is fully done, you have the Private Key and the Certificate is ready to be exported and imported on the other servers, e.g. Edge and Reverse Proxy


7 Best Practice

Beside the certificate design and planning process, there are some more point to remember.

I have listed all important areas you must consider during your design and planning process.

Network Interface Cards:

You have to use two NIC, one for internal and one for external communication. The default gateway has

to be set on the external facing NIC, while you must use “persistent static routes” to all you internal

networks. The DNS should be pointing to the internal DNS Server, if you are choosing an external DNS or

a DNS in a DMZ, make you can resolve the internal Lync Server, if you can’t, you need to provide a hosts

file.

Edge Server and Reverse Proxy combination

As stated earlier, the full feature set in Lync is only available if you make user of Edge Server, Reverse

Proxy and all required external DNS entries (incl SRV Records). If the RevProxy is not deployed, you will

miss the following features, e.g. address book download, location information, device update, Lync Web

App and NON-DOMAIN Client login)

The non-domain client login requires an authenticated access the Certificate Provisioning Service.!

Also the App Store and Mobile Clients can’t login without the publish autodiscovery services.

This is the same with access to Exchange Web Services (EWS).

Director Server Service

The Director Server is an optional component, responsible for offload user authentication and pool

redirection. IT also provide an additional layer of protection for external client connections.

Revers Proxy Listener

Keep the Web Listener as limited as possible. Us only one (1) Listener per internal destination server

each. Make sure the Listener can work with the Hybrid Certificate to minimize costs.


References:

Request and Configure a Certificate for Your Reverse HTTP Proxy (Technet)

Certificate Summary - Single Consolidated Edge with Private IP Addresses Using NAT (Technet)

Certificate Summary - Single Consolidated Edge with Public IP Addresses (Technet)

Certificate Summary - Scaled Consolidated Edge, DNS Load Balancing with Private IP Addresses Using

NAT (Technet)

Certificate Summary - Scaled Consolidated Edge, DNS Load Balancing with Public IP Addresses (Technet)

Certificate Summary - Scaled Consolidated Edge with Hardware Load Balancers (Technet)

http://technet.microsoft.com/en-us/library/gg429704

http://technet.microsoft.com/en-us/library/gg398519

http://technet.microsoft.com/en-us/library/jj204747.aspx

http://technet.microsoft.com/en-us/library/gg425921.aspx


http://technet.microsoft.com/en-us/library/jj205399.aspx


lync certificate planning and assignments

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