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I'm working for company that has nobody who knows anything about Exchange, AD and anything Microsoft. And we have couple of products that work with Exchange so we need to have test environment to be able to test and develop them. Since both products are "mine" it was decided I am Exchange expert and my job was to provide that test environment.

We are using AWS virtual machines so I setup a VM with Windows 2012 Server, installed AD, DNS and all other services that were required to have Exchange server. On same VM I installed Exchange 2010 server with all roles. OWA was working from the start but I was never able to make Outlook start with any mailbox. For some time OWA was enough to get things going but now we really need to have outlook working with this server.

Issue with outlook is very common: "The set of folders cannot be opened. The information store could not be opened". None of usual fixes work (compatibility, creating new profile, etc.) and I am almost 100% sure outlook can't connect to server due to lack of proper network configuration.

I configured our test domain as testenv.local, machine hosting everything is named vm100.testenv.local. When I manually configure account for outlook I enter either IP address of VM or its host name (I added entry in hosts file so I could use host name instead of IP). When I click "Check name" button on wizard it underlines server and account name so I know it can communicate with server VM (I guess it's AD that it is communicating with but I'm not sure, I don't know much about this stuff). But when I finish wizard and start outlook it hangs a bit on "Loading profile" splashscreen and then displays error message I mentioned earlier.

Since this server supposed to be used by a lot of people (devs, support, consultants) it should be reachable from machines that are not in testenv.local domain (basically everybody works with their VMs which are reachable through vpn network).

I am able to configure outlook to work with the same account as POP3 but we need full features of mailbox with calendar, all folders, etc. so that's not enough.

When I tried https://vm100.testenv.local/Autodiscover/Autodiscover.xml I get response with error 600 which I suppose means that service is responding only web browser is sending GET and POST is expected.

I also couldn't make outlook work with outlook anywhere configured.

I should probably mention that my server is not added to any of "official" DNS servers.

So my question is:

  • what am I missing in my configuration? I think I checked all things recommended (I googled a lot for this)
  • if our network admin should add my server to DNS what exactly should he add? as I said, they say they know nothing about microsoft stuff so I would have to be very explicit about what I need them to do.

UPDATE:

link to ipconfig from server and client machine

As I mentioned before we all are working using VMs accessible via vpn. I personally find whole AWS horribly slow so I work from virtualbox VM I host on my home machine but I don't think it matters (or maybe it does?).

grapkulec
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    You'll probably be flamed more for filling your question with comments about being flamed, and for writing a horrible question (which I removed). – David Makogon Jun 13 '16 at 10:54
  • first off, you have a .local domain name ? it's not a good practice. Ok, now please put the ip config of the server and from a computer, to show us more about your setup. Thanks – yagmoth555 Jun 13 '16 at 12:44
  • @yagmoth555 - yeah, I have .local domain. is that bad practice? it suppose to be only for internal use. server is not reachable from outside our vpn, it's not for anything else than just R&D stuff so I thought it's fine. – grapkulec Jun 13 '16 at 13:42
  • It's bad because when you will generate some certificate for your server it will add some challenge, as you can guess you can't order a .local digicert certificate, so you will finish in a split dns setup. – yagmoth555 Jun 13 '16 at 13:47
  • @yagmoth555 I keep seeing that term 'split dns' a lot when I google for solution to my problem. I even tried to understand what it is about but I got lost. – grapkulec Jun 13 '16 at 13:51
  • Dont check that unless your outlook can connect to your server. It's a problem at the end of the wheel. – yagmoth555 Jun 13 '16 at 13:53
  • @yagmoth555 added ipconfigs you asked for, I'm not sure if they will be any help but if I understood that stuff I probably wouldn't ask this question :) – grapkulec Jun 13 '16 at 13:58
  • On the server run test-servicehealth. On the Outlook client right click on Outlook icon in the system tray while holding the ctrl key. Run the Test email Autoconfiguration with the 2 guess smart check boxes unchecked. What does the log tab show? – smwk Aug 07 '16 at 23:49

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