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Trouble connecting Outlook 2007 to Exchange 2013

Posted on 2014-02-17
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Last Modified: 2016-11-23
Hi Everyone,

I have a problem trying to get Outlook 2007 to connect to a newly installed Exchange Server 2013 Standard on a Windows 2012 Standard server.

Some info on setup –
A new Dell PowerEdge T420 Server Dual Xeon 2.4GHz Processors
32GB of RAM
4 X 600GB iSCSI 15k RPM drives in a RAID 10 setup
C: Drive 1.2TB
Windows 2012 Standard server
Exchange 2013 Standard
Both Mailbox and Client Access roles installed on this server
We have an old Dell server running Windows 2003 Server with Exchange 2003 to be retired after the upgrade. I figured it would be much easier to just export the mailboxes and then re-import them into the new server since there are only 10 mailboxes and if I am not mistaken there isn’t a migration path from 2003 to 2013 which is fine with me seems like more headache if there were for only 10 mailboxes.

So in order to prevent any problems I decided to give this new server a different domain name. The old server was mycompany.local, so for this one I used something like newcompany.local. I setup the domain controller and AD DS all the goodies with all the updates all the way to CU3. On the workstations which I joined to the new domain newcompany.local I installed the updates for Outlook 2007 to December 2012. When I use OWA I am able to connect and see the mailbox and send e-mail to other users in the Exchange 2013 and then log in under their account and see that they received the e-mail so I know that part is working, BTW this is all on premises local intranet, I haven’t tried from the Internet yet. However, when I try to open Outlook 2007 which by the way I manually setup Outlook and it says it finds the Exchange and verifies the user name but when I go to open it I get this famous dialog box –

Cannot start Microsoft Office Outlook. Cannot open the Outlook window. The set of folders cannot be opened. The attempt to log onto Microsoft Exchange has failed.
I have tried this on another server (created another 2012 server with Exchange 2012) and another workstation and the same thing, so I know I am missing something. Why OWA works (internally) and not Outlook 2007. I have read on Microsoft website and it was my understanding that a self-signed certificate will work for internal use, but then I read elsewhere you MUST have a 3rd party certificate a UCC certificate and I understand that you need it for external clients on the Internet and mobile but do you need it internally Intranet?

Oh BTW, in case it makes any difference the workstations are running Windows XP w/SP3 and Office 2007 with SP3 also. I have read thru most of the treads here and see nothing related to my problem.

Any help in pointing me in the right direction is greatly appreciated. I have been at this for almost two weeks. I feel like I have taken a crash course on everything I ever wanted to know about Exchange 2013 LOL!!! Please let me know if you need any additional information.

Thanks.
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Question by:mkhatib
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Expert Comment

by:jimmithakkar
ID: 39866529
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Author Comment

by:mkhatib
ID: 39866576
Hi,

Thanks for your reply. I just realized after changing so many things back and forth I forgot to change the DNS address on the workstations to point to the server. Now that I did this is the original dialog I was getting from Outlook 2007.

Cannot open your default e-mail folders. You must connect to Microsoft Exchange with the current profile before you can synchronize your folders with your offline folder file.

I tried those link and unfortunately none of them helped.

Thanks.
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Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 39866683
So, more than likely your problem is being caused by cached credentials from the old domain still being stored on the XP machines.

To clean those up follow this Blog Post's instructions:
http://www.interworks.com/blogs/jvalente/2010/02/02/removing-saved-credentials-passwords-windows-xp-windows-vista-or-windows-7

Why OWA works (internally) and not Outlook 2007.

The two are not related -- OWA is running directly on your server and is not a client application.  Outlook runs on the workstation and is dependent on the settings and configuration of that computer.

Jeff
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Author Comment

by:mkhatib
ID: 39866709
Ok, I tried that and it came up empty nothing stored.

You would think Microsoft would put out better error message that can pinpoint the problem.

Well at least I am learning some new tricks.

I can't believe I am the only person with this problem. I found a lot searching the web but mostly they are saying you need 3rd party certificate even for internal clients. I have to believe that some people at least got the server up and running with at least one internal client before getting a public certificate.

Thanks.
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Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 39866970
Sorry, I must have glossed over your comments earlier about the SSL Certificate.  You don't need a 3rd party cert, but you can't use the generic self-signed one either.

Follow this blog article to issue a proper certificate from the server's CA:
http://exchangeserverpro.com/exchange-2013-ssl-certificate-private-certificate-authority/

Jeff
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Author Comment

by:mkhatib
ID: 39867460
Thanks, I will give it a try today and report back. Hopefully that's the problem.

Mazen
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Author Comment

by:mkhatib
ID: 39867655
Ok I tried to do what they said but I couldn't get to that website. I am assuming that is domain controller address they have up there http://e15dc1/certsrv. I substituted e15dc1 with the name of my server. I keep getting an error HTTP Error 404 - File not found. Actually when I use HTTP it says it's forbidden and that I must use HTTPS and when I do I get that file not found. I even tried https://localhost/certsrv still the same thing.

The article didn't (at least I didn't see) say exactly what that address was, at first I thought I was going to website on the internet.

Maybe I am doing something wrong.

Thanks.

Mazen
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Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 39869005
You have to install Certificate Services Role in order for this to be accessible.

Jeff
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Author Comment

by:mkhatib
ID: 39869058
Thanks, I will give that a try now.

Mazen
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Author Comment

by:mkhatib
ID: 39869112
Ok I added the role by going into Server Manager -> Add Role -> Active Directory Certificate Service, accepted all the default but instead of Enterprise I did Stand Alone. It was successful in installing it. Now I went to the website http://localhost/certsrv, https://localhost/certsrv even used the server name http://w2k12Server/certsrv and https://w2k12Server/certsrv and still none of them worked.

The only thing I didn't do was reboot the server but I did check on reboot if requried after install and it didn't.

I no longer have any hair left LOL!!!

Thanks,
Mazen
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Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 39869187
I guess I should have given you the full tutorial on installing Certificate Services:
http://careexchange.in/how-to-install-certificate-authority-on-windows-server-2012/

Jeff
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Author Comment

by:mkhatib
ID: 39869431
I went to the link and followed all the steps. For some reason Step#10 didn't show anything on my browser so I skipped that and entered http://servername/certsrv and that page came up. So now I went to Exchange to generate the CSR and noticed a blank entry (no name) but there was a certificate, not sure where that came from but it seems it must have been generated just now because it has today's date and time. So like an idiot I went in there and clicked on services SMTP and IIS, and I guess clicking IIS made a mess now I can't get back into Exchange Access Center I keep getting invalid certificate apparently it was generated for a different computer but I kept all the default so now I am stuck.

Is there anyway to undo what I did to get EAC back. If I uninstall the Certificate Role would that help and then re-install it?

I sincerely appreciate your patience trying to get me running. I feel I am so close but no cigars yet.

Thanks,
Mazen
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by:Jeffrey Kane - TechSoEasy
ID: 39871474
Only if you created a restore point prior to doing what you did, or have a full backup that was run prior to doing what you did.

Jeff
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Author Comment

by:mkhatib
ID: 39875944
Hi Jeff,

I am re-installing Windows and Exchange and will follow up tomorrow with an update. I am hoping your solution will fix the problem. Thanks for your patience.

Mazen
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Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 39880472
Not sure why you are reinstalling, but you may want to look at this:
http://www.em-soft.si/myblog/elvis/?p=342
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Author Comment

by:mkhatib
ID: 39881593
Because I didn't have a backup for the test server and I made so many changes I thought it is better to start over again clean. Almost done but this time I did a full backup I am just going to install the certificate role and and look at your latest suggestion. Thanks.
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Author Comment

by:mkhatib
ID: 39884751
Hi Jeff,

First thanks for your patience. I finally did everything and looks like it got installed correctly and I was able to generate the certificate and install it.

However, when I went to try to configure Outlook 2007 I got the same error I got before. I also pulled up the IE and typed in https://servername/ to see if I could access it and funny thing it said it was trusted but the certificate had expired, I thought that was weird how could it be I just generated it and it's good for 2 years (not sure why it defaulted to two years I thought somewhere I accepted 5 years), anyway I took a closer look at the certificate detail and noticed it's not effective until tomorrow the 25th and right now it's 24th LOL!!!! picky picky. So I will wait another hour or so for the 25th and try again. I am still keeping my finger crossed.

While I am waiting I do have a couple questions related to install the CA and completing the certificate. When I installed the CA role for some reason it generated a blank name certificate and it's valid, After accepting the certificate it also generated a second blank certificate, why is that? Should I leave them in there or delete them?

In regards to your previous post above about XP, it's my understanding that XP is only a problem if it's from the internet not inside is that correct? I am not using autodiscover, I am manually configuring Outlook. As for the Internet only smartphones will be connecting both Android and iPhone, if any Laptops it will most probably be Windows 7.

Thanks again.
Mazen
0
 

Author Comment

by:mkhatib
ID: 39884868
Unfortunately it didn't work. Any other suggestions?

I can't beleive I am the only one having this problem.

BTW, after completing the certificate I checked the IIS service, IMAP and POP were already checked and greyed out. Should I be checking any other services i.e. smtp?

Thanks again.
Mazen
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Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 39884933
Firstly, you should know that autodiscover is used both internally and externally, so you do need to have the proper certificate settings for internal to work correctly.

To be honest, I wouldn't try to install an Exchange Server 2013 without a third-party certificate.  It's just so much easier, and the cost is minimal.

Had you done that from the start, you would be up and running already.  

So, while this is a fun puzzle to figure out, its not one that I think is worth the effort.

Jeff
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Author Comment

by:mkhatib
ID: 39884948
Do you have any recommendation where I should get a 3rd party certificate for Exchange? Also which URL addresses should be included for the certificate? I am assuming I need a UC Certificate correct?

The problem was I was under the impression I could use a self serve certificate and when I started having these problems my thought was to fix them before committing to a 3rd party certificate so I would know what I need.

I appreciate you hanging in this long and understand you giving up on solving this. I will try the certificate and hope it works. I am now trying my laptop running Windows 7 Pro with Outlook 2013 to see if I get the same problem. I just want to make sure it's not Windows XP or Outlook 2007 otherwise I will need to upgrade everyone.

Mazen
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Author Comment

by:mkhatib
ID: 39884968
I thought you might be interested to know that using Windows 7 Pro and Outlook 2013 worked right away no problem. So now I need to narrow it down to either XP or Outlook 2007. Thanks again.

Mazen
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Accepted Solution

by:
mkhatib earned 0 total points
ID: 39884978
Dear Jeff,

I ended up deleting Outlook 2007 profile and re-creating it with autodiscovery this time and it works. It now opens up and connects. I sincerely appreciate all your help, I am sure without it, it would have taken me a lot longer to solve this. I never had this much problem with all the previous Exchange from 5.5 to 2010, this takes the cake.

I will be looking for a 3rd party certificate now and hope the rest will be easier.

Thanks a million.
Mazen
0
 

Author Closing Comment

by:mkhatib
ID: 39897027
Having a valid certificate was the main problem for Outlook 2007 not working and as Jeff mentioned it would have much easier had we got a 3rd party certificate. I will know for sure once I get it. Thanks for hanging in there. Plus I was given a lot of good resources.
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