Exchange 2013. Outlook stuck at connecting

Question

I set up 4 Exchange 2013 (cu20) servers (Mailbox+Client Access) on Win 2012 R2, at two different locations. Two at location A and Two at location B. They are internal servers and there are no internet facing server.

Location A:
10.23.4.31 serverA1.ex.com
10.23.4.32 serverA2.ex.com

Location B:
10.23.16.7 serverB1.ex.com
10.23.16.8 serverB2.ex.com

All of them installed correctly. I can set up a DAG that include all the servers and database copies work fine across all servers. Same SSL cert from internal CA also installed to all servers.

Outlook Anywhere connects fine when it chooses a server at location A. However, it stucks at trying to connect when it chooses a server at location B. Additionally, I cannot access OWA (times out) at servers in location B.

Firewall should be good because servers at Location B works fine when they were running Exchange 2010 for both Outlook and OWA. Nothing else has been changed since the upgrade. DNS works, Ping works..

I followed the same installation procedure for all the servers.

What could be the problem on the servers at location B?

score 0 · Answer 1 · answered Jun 25 '18 at 17:34

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what does the https://testconnectivity.microsoft.com/ say when you run it in location B?

It happens that sometimes upgrade from 2010 to 2013 alters bindings in IIS. Let's try to narrow down where the issue is.

Marius

answered Jun 25 '18 at 17:34

Marius

1

1

I cannot run it. These servers are in internal network. There are no internet connection.. – Aizul W Jun 25 '18 at 23:49
OK! let's try the following: – Marius Jun 26 '18 at 14:31
1. Can you reach IIS using web browser? `http://yourIPaddress` – Marius Jun 26 '18 at 14:32
Good news, I managed to solve the problem! +1 for basic http/network troubleshooting! – Aizul W Jun 27 '18 at 01:03
Hi Aizul, very good news. It is a shame that we have not been able to really find the reason of your problem, but resolving the problem is the main goal, so happy for you. – Marius Jun 27 '18 at 11:43

score 0 · Answer 2 · answered Jun 26 '18 at 08:36

0

How do you "choose a server at location B", manually configure Outlook profile and enter server name? How about do it by autodiscover service to auto configure Outlook profile?

Moreover, I recommend to set an unified host name of Outlook Anywhere, OWA and other Exchange services, then use NLB or HLB for load balance.

answered Jun 26 '18 at 08:36

Jianfei Wang

387
1
4

Outlook automatically chooses a server to connect to. But you can also choose a server manually by going to **Exchange Proxy Settings** for Outlook Anywhere. However, Outlook will not keep the preferred server after that. You can `Ctrl+Click` on Outlook notification icon and choose **Connection Status** to check the server it is connecting to. Good news, I managed to solve the problem! – Aizul W Jun 27 '18 at 01:00

score 0 · Accepted Answer · answered Jun 27 '18 at 01:29

Good news! I managed to connect Outlook to the servers at location B and browse OWA on those servers.

I ended up uninstalling Exchange 2013 from servers at location B. After that I uninstalled IIS and all features related to Web. Then, rebooted the servers. Once they're up, I cleaned up registries using CCleaner and make sure there are no more leftovers registries from Exchange. Then, I rebooted again. After that, I deleted Exchange's V14 (2010) and V15 (2013) folders in Program Files and deleted inetpub folder in C:. I used CCleaner again to clean the related registries and reboot them.

Finally, I followed the same procedure to install Exchange 2013 on each server, one at a time. The first thing I checked once they successfully installed was OWA and I could browse it at each server with no problem. Then, I added each servers to existing DAG and make database copies on them. Finally, I tested Outlook and manually connect to the servers at location B and the result is Outlook connect with no problem! Unfortunately, as for serverB1, Outlook keeps requesting for credentials but good thing is, it still connects successfully.

I hope this answer will help others.

Exchange 2013. Outlook stuck at connecting

3 Answers3