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I have an SBS2011 that has Microsoft Exchange operating on it. I just installed a new win 7 client at the office and now when I try to setup Outlook (version 2010) a new window pops up asking for user and password. I provide that and check the "Remember my password" but it continues to ask for my password.

I have had some problems with certificates, namely one ran out and I didn't provide a new one until now, could that be the reason?

The setup now are 3 servers, one Server 2012 r2 which holds the FSMO roles, the SBS 2011 is a file server and Exchange server and Server 2008 r2 is an SQL server. The 2012 r2 is the Certificate Authority and on the SBS 2011 I have the certificate role setup and it gets signatures from the CA (self signed) on the 2012 r2 server.

I admit that I am a newbie at certificates, specially when it comes to creating some specific ones like for Exchange. What I did to create the signature that is being used now by the website for https://remote.domain.com/OWA and https://remote.domain.com/RPC was to go into IIS Admin, select Server Certificates and in there Create Domain Certificate. In there I put remote.domain.com as the Common name, Domain as Organization, Server as Organizational unit and filled out the rest also (they don't matter do they?). In the next step I chose the Certificate Authority from Server 2012 and some Friendly name.

Then I went into Default Web Site in the IIS Admin and chose Binding and associated the newly created certificate to that website.

But now I can't set up outlook on client computers, the setup procedure won't go past asking for user and password, just repeats that until I press cancel and then it says that Exchange has to be online (which it is, clients with already setup emails work fine).

Any ideas on what could be wrong or what I could do to debug this?

=== EDIT ===

So I moved the FSMO roles to the SBS server and restored it to its (begin mock) full greatness (end mock). I still have the same problem, I can't add new accounts to Outlook or with the Mail program in Control Panel. I don't get any errors in Event Viewer, it's just as if whatever mechanism (unfortunately its a black box to me so I can't debug this properly) is involved in contacting the Exchange server is failing by some reason and says that either Outlook is offline or Exchange is offline which is not true since I can go to an old computer with Outlook already set up and it works fine in contacting Exchange, it sends emails and receives them and syncs to the server just fine. So there is just this hurdle of adding new accounts, something there is very much wrong and I have no idea what it is. I can't add new accounts on either new computers or old computers that have already working Outlook. Any idea of what is causing this?

I understand that there is some kind of autodiscover involved with Exchange and I did try to right click the outlook icon with ctrl pressed and test the autodiscover which seemed to me give satisfactory results but as a non-expert in Outlook/Exchange then I have no idea of how that autodiscover should look like but to an untrained eye it did look ok.

  • one Server 2012 r2 which holds the FSMO roles - How did you manage that? The SBS server must hold the FSMO roles, AFAIK. – joeqwerty Apr 12 '16 at 11:18
  • @joeqwerty that is true, but when moving from SBS to full server you can move the FSMO roles and have both servers working for a grace period of 21 days. That period has now expired and I am still stuck with Exchange on the SBS unfortunately. You think that is causing this issue? – ojs Apr 12 '16 at 11:35
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For SBS, you need to use the wizards. Re-running the setup wizards in the console and not changing anything will issue a new SSL certificate. However you should really be using a trusted SSL certificate.

Repeating authentication prompts is classic SSL certificate issues.

As for the FSMO roles, you need to move them back, as you are technically in violation of the licence. While you do have a grace period, if you have exceeded that then move them back until you are in a better position to proceed.

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