troubleshooting Question

Exchange 2013 OWA External Timing Out

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Stephen HopkinsFlag for United States of America asked on
6 Comments1 Solution72 ViewsLast Modified:
Original Configuration:
Two External IPs (.1,.2)

DNS -> .1 -> .2 -> .2

Network Security Appliance
Both IPs come through one WAN port
.2 is the primary
.1 is an alias

Firewall Port Forwarding
.2 (HTTPS, SMTP,POP3,) -> Server 2008 with Exchange 2007
.1 (HTTPS, SMTP, POP3, POP3_995, SMTP_687, HTTP, IMAP_993, IMAP_143) -> Server 2012 R2 with Exchange 2013
MX Records are pointing to -> Server 2012R2 with Exchange 2013

The servers are operating in co-existence.   The mailboxes, public folders, etc. are all on the Exchange 2013 server.
OWA to the Exchange 2013 is working.  
ActiveSync to the Exchange 2013 is working.

=== Server 2008 with Exchange died ===

I made the following changes.
Changed mail from pointing to .1 to pointing to .2
Removed the port forwarding (HTTPS, POP3, SMTP) to .2 (Exchange 2007)
Deleted the .1 alias in the firewall
Changed the port forwarding for Exchange 2013 (HTTPS, SMTP, POP3, POP3_995, SMTP_687, HTTP, IMAP_993, IMAP_143) to now respond to .2

POP3 works with Internal Outlook Clients
OWA works internally
ActiveSync works internally

What does not work...
External OWA
External ActiveSync

I tested with the domain name as well as the IP.

HTTP does work.  It provides the correct 404 page.

What I get when I access OWA Externally using

The Outlook Web App screen displays
Still working on it ...
Site can't be reached.

Everything works inside but not outside.   Any ideas?
timgreen7077Exchange Engineer
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