Outlook cannot connect to exchange but OWA can

[zznate]

Hi,

Ive built a new exchange 2019 environment on windows 2019 server (twice) and each time i get the following error when trying to connect my outlook on the win10 client to exchange 

"Cannot start Microsoft Outlook. Cannot open the Outlook window. The set of folders cannot be opened. The information store could not be opened."

I can open up OWA and send mail (Send connector working) and i have configured the records for autodiscover and mx records.

When i go through the mail option in control panel to setup profiles it successfully pulls the profile from the exchange server and creates the OST file.

Ive tried opening outlook in /safe mode and /resetnavpane.

Also disabling firewalls, antivirus, uninstalled skype and tried reinstalling office.

I have a certificate chain that the system is happy with and dont get any messages.

I've followed the exchange deployment assistant and don't feel i missed any steps. The environment is not connected to the internet and only needs to send mail in a small intranet.

I cant seem to find any logs on the client which may suggest why the outlook client gives that error.

 
I downloaded the troubleshooter EMT tool and it confirms that things should be working.

I'm out of ideas here and would love any advice or ideas to what i may have missed

Thanks for your time and support

Regards,

Nathan

[#2]

I tried a 2016 version of outlook to see if that changed anything but similar error.

Tried a different version of exchange 2019 and no luck.

I can still connect to the exchange and download the OST file in control panel\mail. It tells me my profile was successfully setup but outlook still wont load and errors on boot up

[#3]

Did you ever figure this out?

I did a test restore of an Active Directory server and an Exchange 2019 server in an offline/disconnected network. Everything works fine except Outlook 2016 gives me a similar error (but instead of mentioning the Information Store, it says "The set of folders can't be opened. You must connect to Microsoft Exchange with the current profile before you can synchronize with your Outlook data file.").

Like your situation, OWA works perfectly fine and mail flows between internal mailboxes using OWA. Connecting Outlook 2016 succeeds in connecting to Exchange (all green arrows, autodiscover working fine), and the profile is successfully created, but then when Outlook loads to the Inbox, that message appears.

I find it interesting that in both your case and mine, there is no Internet. This was restored from a perfectly working Exchange 2019 server that is still in production, the only difference being no Internet for the test restore network.

[#4]

I figured out what is happening.

After verifying the Exchange connection and setting up the profile successfully, the Outlook client pings the default gateway before connecting to the Information Store. If the ping is not successful, Outlook stops and reports that it either can't open the information store or that it can't open your profile's set of folders. This happens even though when you set up the profile, it successfully connected to Exchange.

So in my test environment, where the client machine was getting a default gateway through DHCP, but where that default gateway didn't actually exist, I had to set a static IP address on the client machine, and used the AD server in my restore environment as the gateway. Even though it won't really route any traffic, it was enough for Outlook to get an ICMP response from the server to fake it into thinking the gateway was up, and I was able to load Outlook with no issues after that.

@zznate