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

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1 Lync Certificate Planning and Assignments (Edge, Reverse Proxy, Director, Frontend, Mediation, WAC) Copyright and written 2013 by Thomas Pött, MVP Lync/ Unified Communication Blog: 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.

2 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

3 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 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.

4 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.

5 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

6 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.

7 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 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 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.

8 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: SIP PRIMARY DOMAIN: SIP Secondary Domain: INTERNAL.AD DOMAIN.COM 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 1 st 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

9 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. SIMPLE TOPOLOGY LAN DMZ INTERNET PKI internal Lync Front End Office Web Apps edge.internal.ad sip.internal.ad SAN*: fe01.internal.ad sip.(alldomains) lyncdiscoverinternal.(alld omains) dialin.domain.com meet.domain.com wac01.internal.ad Lync Edge Reverse Proxy Listener01: To Lync Front End Listener02: To Office Web Apps SAN: sip.domain-a.com sip.domain-b.com webconf.domain.com webext.domain.com SAN: webext.domain.com *.domain.com *.domain-a.com *.domain-b.com Public CA *) 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.

10 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. COMPLEX TOPOLOGY *) 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 PKI internal pool01.internal.ad SAN*: pool01.internal.ad fe11.internal.ad fe12.internal.ad web01ext.domain.com dialin.domain.com meet.domain.com pool02.internal.ad SAN*: pool02.internal.ad fe21.internal.ad fe22.internal.ad web02ext.domain.com dialin.domain.com meet.domain.com sip.internal.ad SAN*: dir11.internal.ad dir12.internal.ad webdirext.domain.com meet.domain.com dialin.domain.com lyncdiscoverinternal.(alld omains) Office Web Apps LAN DMZ INTERNET Lync Front End Pool01 Lync Front End Pool02 Lync Director Pool edge.internal.ad SAN: edge.internal.ad edge11.internal.ad edge12.internal.ad SIP.alldomains + Simple URL + Mobility + WebService wac01.internal.ad Lync Edge Pool Reverse Proxy Listener01: To Lync FE Pool01 Listener02: To Lync FE Pool02 Listener03: To Director Pool, simple URL, mobility and its WebService Listener04: To Office Web Apps SAN: sip.domain-a.com sip.domain-b.com av.domain.com webconf.domain.com webext.domain.com SAN: webdirext.domain.com web01ext.domain.com web02ext.domain.com *.domain.com *.domain-a.com *.domain-b.com Public CA

11 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.

12 GEORGRAPHICALLY deployed COMPLEX TOPOLOGY LAN DMZ INTERNET Datacenter US pool01.internal.ad SAN*: pool01.internal.ad fe11.internal.ad fe12.internal.ad web01ext.domain.com dialin.domain.com meet.domain.com sip.internal.ad SAN*: dir11.internal.ad dir12.internal.ad webdirusext.domain.com meet.domain.com dialin.domain.com lyncdiscoverinternal.(alldom ains) Internally, you have two choises: 1.) user two independen DNS Server Zones 2.) use a GEO Load Balancer for your internal deployment Lync Front End Pool01 Lync Director Pool USA Office Web Apps edgeusa.internal.ad SAN: edgeusa.internal.ad edge11.internal.ad edge12.internal.ad SIP.alldomains + Simple URL + Mobility + WebService wac01.internal.ad Lync Edge Pool USA Reverse Proxy USA Listener01: To Lync FE Pool01 Listener02: To Lync FE Pool02 Listener03: To Director Pool, simple URL, mobility and its WebService Listener04: To Office Web Apps SAN: sip.domain-a.com sip.domain-b.com av.domain.com webconf.domain.com webdirusext.domain.com Public CA SAN: webdirusext.domain.com webdirgerext.domain.com web01ext.domain.com web02ext.domain.com *.domain.com *.domain-a.com *.domain-b.com e.g. KEMP GEO LOADMASTER Deployed 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. *) 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 PKI internal DMZ Datacenter GERMANY pool02.internal.ad SAN*: pool02.internal.ad fe21.internal.ad fe22.internal.ad web02ext.domain.com dialin.domain.com meet.domain.com sip.internal.ad SAN*: dir11.internal.ad dir12.internal.ad webdirgerext.domain.com meet.domain.com dialin.domain.com lyncdiscoverinternal.(alldom ains) Lync Front End Pool02 Lync Director Pool GERMANY edgeger.internal.ad SAN: edgeger.internal.ad edge21.internal.ad edge22.internal.ad SIP.alldomains + Simple URL + Mobility + WebService Lync Edge Pool GERMANY Reverse Proxy GERMANY Listener01: To Lync FE Pool01 Listener02: To Lync FE Pool02 Listener03: To Director Pool, simple URL, mobility and its WebService SAN: sip.domain-a.com sip.domain-b.com av.domain.com webconf.domain.com webdirgerext.domain.com SAN: webdirusext.domain.com webdirgerext.domain.com web01ext.domain.com web02ext.domain.com *.domain.com *.domain-a.com *.domain-b.com Listener04: To Office Web Apps wac01.internal.ad Office Web Apps

13 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 Primary SIP domain SAN 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 Type Configuration Comment 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) Type Configuration Comment Common Name Primary SIP domain

14 SAN 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

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

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

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

18 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:

19 Verify the correct CN and SAN entries:

20 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!

21 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

22 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.

23 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)

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