This is the first Exchange migration I have done with multiple Exchange servers (and each server has multiple roles). Can someone help me fill in the blanks? I would like this to be a streamlined as possible, but I am not sure of the best configuration of the URL's to accommodate my environment. Can this be setup so that all users go to a single URL internally and externally regardless of the site their mailbox is located (have OWA, OAB, ActiveSync, and Outlook Anywhere all use the same URL both internally and externally)? I know Exchange does its own proxying, I'm just not sure if it's complex enough to sense what we are doing here.

   The Exchange environment is virtually untouched at this point. The only thing that has been done is that I have installed/patched the OS on the machines that will host the new Exchange environment. Any advice direction will be greatly appreciated.







Here are the environment details:



AD/Network Info:

AD Domain FQDN: contoso.com

AD Forest/Domain DNS Zone: contoso.com

AD NETBIOS Name: CTS

AD Sites: There are (2) sites as follows: "CLE" (Cleveland) | "CHI" (Chicago)

Subnets: CLE: 10.10.10.x | CHI: 10.10.11.x

The two AD sites are joined by a point-to-point link

Forest/Domain Functional Level: 2003

Domain Controllers: There are a total of (3) DC's. All DC's run Windows Server 2012 R2. (There are (2) DC's in Cleveland and (1) DC in Chicago). None of the new Exchange 2013 servers will be domain controllers.





Existing Cleveland2007 Exchange Server Info:

Internal hostname: cleex01.contoso.com

IP Address: 10.10.10.20

OS: Windows Server 2003

AD Site: CLE

Function: Exchange 2007 Server

Ex Roles: CAS/MBX/HT

Internal OWA URL: cleex01.contoso.com/owa

External OWA URL: not configured

Internal ActiveSync URL: cleex01.contoso.com/Microsoft-Server-ActiveSync

External ActiveSync URL: owa.contoso.com/Microsoft-Server-ActiveSync

Internal OAB URL: owa.contoso.com/OAB

External OAB URL: owa.contoso.com/OAB

External Outlook Anywhere URL: owa.contoso.com



New Cleveland2013 Exchange Server Info:

Internal hostname: cle-ex.contoso.com

IP Address: 10.10.10.230

OS: Windows Server 2012 R2

AD Site: CLE

Function: Will be Exchange 2013 Server

Ex Roles: CAS/MBX/HT (Has HT been deprecated in 2013?)

Internal OWA URL: To be determined

External OWA URL: To be determined

Internal ActiveSync URL: To be determined

External ActiveSync URL: To be determined

Internal OAB URL: To be determined

External OAB URL: To be determined

External Outlook Anywhere URL: To be determined





Existing Chicago2007 Exchange Server Info:

Internal Hostname: chiex01.contoso.com

Internal IP Address: 10.10.11.20

OS: Windows Server 2003

AD Site: CHI

Function: Exchange 2007 Server

Ex Roles: CAS/MBX/HT

Internal OWA URL: chiex01.contoso.com/owa

External OWA URL: not configured

Internal Exchange ActiveSync URL: chiex01.contoso.com/Microsoft-Server-ActiveSync

External Exchange ActiveSync URL: not configured

Internal OAB URL: owa.contoso.com/OAB

External OAB URL: owa.contoso.com/OAB

External Outlook Anywhere URL: owa.contoso.com





New Chicago2013 Exchange Server Info:

Internal hostname: chi-ex.contoso.com

IP Address: 10.10.11.203

OS: Windows Server 2012 R2

AD Site: CHI

Function: Will be Exchange 2013 Server

Ex Roles: CAS/MBX/HT (Has HT been deprecated in 2013?)

Internal OWA URL: To be determined

External OWA URL: To be determined

Internal ActiveSync URL: To be determined

External ActiveSync URL: To be determined

Internal OAB URL: To be determined

External OAB URL: To be determined

External Outlook Anywhere URL: To be determined



Existing internal DNS entries:

owa.contoso.com: Internal IP address of the CLE Exchange server

autodiscover.contoso.com: Does not exist





Existing external DNS entries:

owa.contoso.com: External IP address of the CLE Exchange server (uses a firewall PAT)

autodiscover.contoso.com: Does not exist

clesrv.contoso.com: External IP address (uses a firewall PAT) of Cleveland Exchange 2007 server

chisrv.contoso.com: External IP address (uses a firewall PAT) of Chicago Exchange 2007 server

contoso.com MX records: MX1: clesrv.contoso.com | MX2: chisrv.contoso.com





New/Changed/Proposed internal DNS entries:

owa.contoso.com: To be determined

autodiscover.contoso.com: To be determined

legacy.contoso.com: To be determined







New/Changed/Proposed external DNS entries

owa.contoso.com: To be determined (will use a firewall PAT)

autodiscover.contoso.com: To be determined (will use a firewall PAT)

clesrv.contoso.com: To be determined (will use a firewall PAT)

chisrv.contoso.com: To be determined (will use a firewall PAT)

contoso.com MX records: MX1: To be determined | MX2: To be determined

Any others needed/recommended?