Questions[outlook-2010](server)

Right now, we've got a business critical application that installs an Outlook add-in. It is a bit slow to load, which makes Outlook 2013 kill it after a few runs, but I've mitigated the issue of Outlook 2013 killing the add-in by using the Office 2013 Group Policy Administrative Templates "List of managed add-ins" policy.

I don't see a similar policy in the 2007/2010 templates, and have to remove the resiliency key from the user's profile whenever the key gets added for whatever reason. Is there a way that I can replicate the functionality of the 2013 policy for 2007 and 2010, or even disable resiliency entirely if granularity is not an option? If so, how?

I've found several ways to selectively kill the plugin-specific resiliency subkey automatically, but this still requires the user to restart outlook if the plugin doesn't load because it was disabled automatically.

A user is experiencing a problem whereby when sending emails, some emails are being allocated the same Message ID. The issue looks to occur when the user has a draft email and they forward the draft to one person, and then later send the draft to another person.

I have done an email trace in Exchange, searching only on Message ID and Exchange is returning the two emails.

Our environment is Outlook 2010 SP1, Exchange 2010 + Exchange 2007, our users run in Outlook Cache Mode.

I have done some research and from what I have read it is the client which generates the Message ID, is this correct?

Is anyone aware of any known issues with two different emails receiving the same Message ID? Does anyone have any knowledge on how this could occur and what we can do to resolve this?

The latest example email's were sent just over 1 hour apart (1 hour, 1 minute), have the same subject, Message ID, sender, but different recipients and message body (only slightly).

Background

My VPN connection does not have its own Network adapter as a result all DNS queries are sent down my Internet connection. My VPN connection works fine handling requests to a specific IP address range: 192.168.x.x.

The Question

I want to specify my Server in my outlook account settings using an IP address so Outlook can connect to Exchange over my VPN. However when I change the setting it goes off finds the host names and uses that instead - as a result when trying connect over VPN cannot connect as cannot resolve the host name. How can I force it to use the IP address??

The majority of my Exchange users are all on Windows 7 and have no issues (at least using Outlook...) but a subset of the executives are ardent Mac users running Outlook 2011 for OS X. One of these clients is prompted every 5-10 minutes for credentials. Ticking the checkbox to remember credentials does not fix the situation.

Mac version is 10.7.2.

I have already removed and rebuilt the EWS virtual directory on my Client Access server.

Outlook anywhere is set to NTLM authentication.

None of the Microsoft clients are experiencing this issue.

What else can I do to make this issue go away?

I have one Exchange 2010 server which is fully updated, the clients are running Outlook 2010 but some users are getting a prompt for credentials every time they open Outlook.

I have checked for common errors like the checked box Always request authentication.

I think this happens only with new users that are created in AD and in Exchange and I can't do gpupdate - could that be related?