Outlook keeps asking for password

[REDACTED]

Hello.

I have migrated from sbs2003 to sbs2008 at one of my customers. I then installed Avast SBS Suite on the server and pushed out the client to the maschines in the network. After this Outlook is asking for username and password.
When the password is typed, remember password is selected and OK is clicked the box returns as if some input is wrong.
If we cancel the box with the "red X" in upper right corner everything is OK for a while. Mail is received and sent.
Then after a minute or two the box comes up and asks for username/password again.

This might be a certificate issue.
Installation of the ADNM Console needs a certificate. It does not accept the certificate that the small business server allready uses so I created a new one.

Grateful for any help on this issue!

[REDACTED]

RESOLVED but not satisfying.
During the latest time I have searched the Internet up and down for a solution, but all of the solutions found just helped for a part of the problem and/or resulted in other problems. The list of problems is so long I wont even start on it here. At last the Exchange Information Store was unable to start.
I finaly came across this tread http://forums.techarena.in/small-business-server/574108.htm, when I was searching for a solution to the latest problem on my list, and the post from chace zhang helped out.
I uninstalled Avast! Server (managed) and everything worked fine. The reason this is not satisfying is that I'm not able to tell which part of Avast Server (managed) caused the problem. Since I did not think uninstalling Avast would give any solution I did not try to disable any of the services first to check. It was late at night and my wife called me about christmas preperations so I just uninstalled to try something...and there will be christmas this year too.
Could it be that this version of SBS suite is not quite ready for SBS2008 or could it be that some thing else is causing this to happend.

Should somthing be removed from the installation package? I made an installation package suited for all servers at site (SBS2008, ISA 2006 on separate box ofcourse and SQL2005 also on separate box). Should the install package be tuned for each servertype? It works fine on the other two boxes.

I would appreciate to heere from others whit similar problems and what is the solution to install Avast Server managed to the SBS2008 box?

[scythe944]

Hi kristoball,

I'm a little confused.  Why does outlook ask for a password in the first place?  Are you using the exchange authentication, or are you trying to use POP3 or something?

I have, and some others have installed avast on SBS2008, and although we've had some problems in initially getting everything started (view this topic for more info: http://forum.avast.com/index.php?topic=41775.0), eventually everything worked fine.

I've had no problems whatsoever with exchange in sbs 2008 and outlook 2003 / 2007 clients so far.

Once your ADNM installation get straightened out, it's usually pretty smooth sailing from that point on.

So, if you could tell us if you created a domain, added users, joined the client computers to the domain, and what version of office that you're using, it may help.

Also, yes, you're supposed to create a new certificate as part of the ADNM console installation.  The SBS certificate is for remote access and outlook web access, not for secure access to the AMS server.

[REDACTED]

Hello scythe944 and thank you for responding.

I'm quite confused myself. I can't think of any reason that Outlook should ask for a password. This started after I installed Avast Server (managed).
It's the same password box as when you're using Outlook anywhere and basic authentication, but the Outlook account is an Exchange account on a desktop computer and is not set up for Outlook anywhere.
When we were trying to use the companyweb the webpage came up with an error message showing to some Avast Proxy which could not be found. Removing these Proxy settings from IIS made the companyweb work again but did not help for Outlook. It was not untill Avast Server (managed) was uninstalled the password box stopped popping.

When I installed ADNM on the SBS2008 I had some problems using a SQL database, but with a little help from the topic you are showing to here and also microsofts SQL sites, I managed to solve those issues and have the ADNM working with the database on another server hosting SQL2005.

This SBS2008 box is migrated from an SBS2003 box which some years ago was migrated from a windows2000 based DC. The system uses the old win2000 machine name insted of the new domain name which was created when migrating to the SBS2003 machine. In Win 2000 it was accepted to use a single label domainname. When the domain was migrated to sbs2003 the domain name was changed and added a .local at the end to meet the new standard.
The Office version in the domain is upgraded from 2003 to 2007 after the last server migration but before the Avast installation.

I have done this installation in SBS2003 domains earlyer with non of these problems. I dont think of the certificate as a problem and I know it should be that way.

What I would like to know is if the installation package for the SBS should be different from the installation packages on the other two servers hosting ISA 2006 and SQL 2005?
In case, what should this package contain?
Also, what part of the installation package does the Avast Proxy come from?

[scythe944]

Yeesh.. alright, this scares me a little bit. 

The system uses the old win2000 machine name insted of the new domain name which was created when migrating to the SBS2003 machine.

I'm not quite sure if your server is correctly named and on the domain.

Have you ever ran a dcdiag on the server to see if there were any DNS, naming, or any other errors?  Maybe a netdiag too (I can't remember if that was omitted in 2008 or not, so you might not have it).

What I would like to know is if the installation package for the SBS should be different from the installation packages on the other two servers hosting ISA 2006 and SQL 2005?
In case, what should this package contain?

No, the package is the same, it's just the "server" installation that's supposed to be used.  Really, the only difference between the small business suite for avast, and the standard server versions are pricing and licensing.  The SBS suite doesn't come with anything different.

The avast proxy would probably be included in the web shield.  Maybe try turning that off on one of the clients and see if that helps the outlook issue or not.

Can you tell if the Avast Exchange plugin is running on the server?

Frankly, I don't even know where to start here.  It's really unclear to me where the problem begins.  Whether it's an authentication problem because the server is named incorrectly, or if it's a plugin (exchange or otherwise) that's not functioning like it's supposed to, or maybe a DNS error, pointing to the incorrect server.

Does everything else on this network function properly (besides the avast/outlook issue)?

I'm even more confused than earlier. 

[REDACTED]

Hello.

I might have been a little quick when I wrote the info about domain name/machine name. This shows up only in logon and other password boxes. It is possible in most cases to use the new domain name instead. I have also read a posting about this issue somewhere, sometime, but can't remember where. It should not be too difficult to find it. Anyway, as I can remember, this posting mentioned the issue to be more annoying than crithical, but of course it should be followed up at least to "check it out of the case".

I have not ran dcdiag nor netdiag, but will do that on my next visit to this customer.

I have manualy been checking through DNS for misconfiguration, but the only things I could find there was listings of the old SBS2003 box in most of the containers. These have been removed. I have also been running different best practisses analyzers and corrected all error found.

Everything seems to be running smooth. There has been other issues after the migration, but they have been fixed.

Exchange and SBS2008 is updated with the latest rollup for the latest SP. There are two updates leaving errors and not installing, but I have followed this as well and it does not seem to have anything to do with this issue.

The Avast Exchange Plugin were running before I uninstaled Avast Server. All Avast services where running.
It helped the Avast/Outlook problem when I uninstalled the Avast server, and the problem with companyweb was gone after I removeedd the avast proxy listings from all sites in IIS.

What I'm thinking now is to reinstall the managed Avast server without the web shield, but I would like to know what the web shield does. Is it a firewall or is it scanning for threats? If it is a firewall I don't need it.

Thanks again for your answares. Even if you are more confused and don't know where to start they are helpful hints.