Outlook Connected to Exchange 2016 but when trying to do some other task, kept getting "The connection to Microsoft Exchange is unavailable."

Question

Hi Everyone,

If this is posted on the wrong part of the forum, please help me to move it as I cannot find the option to set it as "exchange".

I hope someone can help me answer this because, after an extensive google, I still cannot find an answer.

I am using a HyperV to host AD and Exchange

System

Host: Dell Server, Windows Server 2016 Std with Anti-Virus and UPS software

HyperV1, Window Server 2016 Std with AD, DHCP, DNS, VPN & file sharing.

HyperV2, Windows Server 2016 Std, Exchange 2016 Std and POP3 connector.

Tested OWA and local profile on Outlook able to connect send and receive emails, nothing much was changed and left as default mainly.

I can connect to Outlook 2013 on a machine that is not part of the domain using a VPN connection. Outlook 2013 shows connected to Exchange.

Under outlook security, encrypt data between outlook and exchange is tick.

Problems I am facing:

When I try to save a new contact or when I try to import emails that I backup to PST, I keep getting this error.

"The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action."

At this point, I did what I can find online but faced the same problem.

The client and his staff are working out of the country. They don't want the devices to join the domain.

Please share with me what is the workaround.

We are planning to set up outlook anywhere with an SSL Certificate later but I like to ensure all are working before we go live.

Answer 1

Hi @Raymond Lee ,

Have you tried to switch outlook to online mode?

If you haven’t. Try switching it to online mode and then exporting emails.

And based on your informaiont.
"We are planning to set up outlook anywhere with an SSL Certificate later but I like to ensure all are working before we go live"

You haven't set up outlook anywhere yet.

According to this document:

I think the issue may occur with VPN. Could you connecto to outlook without VPN?

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