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Out of Office responses to incoming email are an incredibly useful thing to have with any mail server. In Microsoft Exchange, these are sent by the server on behalf of each user when the user has enabled them. Out of Office messages can be configured using the Exchange web portal or using a standard mail client, which has up until now, usually be Outlook. In Lion, Apple has built in an Out of Office setting in Mail.app.

To configure an Out of Office message using Mail in Mac OS X 10.7, first configure the Mail client to communicate with the Exchange server. Then open Mail.app from /Applications. Right-click on the name of the account (or Inbox if you only use one account) and select Get Info from the contextual menu.


Click on the Out Of Office tab and check Send Out of Office Replies to enable the Out of Office message. A different message can be sent to users in your domain than to users outside of your domain; enter the Out of Office Response for users of each.

Out of Office replies will then be sent by the server on behalf of the user account.

July 9th, 2011

Posted In: Mac OS X, Mass Deployment

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In Exchange 2007, the Client Access Server (CAS) role accepts connections from clients in order to allow them access to the Exchange Server infrastructure (mailboxes, public folders, GAL, etc). CAS accepts connections from:

  • POP3 and/or IMAP4 clients
  • Outlook Web Access (OWA) and/or OWA Light clients
  • Exchange ActiveSync (EAS) clients

Entourage falls into this category, and so when you are deploying Exchange 2007 alongside Entourage you will point your clients at your host running CAS.  This is a change from previous versions, where you could enable IIS on any host and point clients there; however, it is similar in that CAS is very similar to the front end functionality that this option entailed.

There are certain design considerations CAS imposes, as well as benefits to how things were handled in Exchange 2003.  With Microsoft Outlook clients, you could migrate a mailbox between Exchange Servers and Outlook would read the new location of the mailbox automatically and reconfigure itself for the new server.  This has never been a feature of Entourage (although you can use a clustered pair), but now you point all clients to your CAS host and the mailboxes can then be moved between Storage Groups and Servers without having to touch the clients.  However, if you change CAS servers you may find yourself performing some client reconfiguration.

In smaller environments, where ports are directly coming into the server from the WAN, you won’t find the CAS role to be a big design consideration.  Clients can simply connect over port 80 or 443 (not including the LDAP lookups obviously).  But in larger environments where all data needs to be proxied in some way, you may find the move to a CAS role complicated.  Here, look to Microsoft’s IAS server, which would be placed into the DMZ and then allow connections from Entourage and other ActiveSync/OWA clients.

A number of people have been asking about ActiveSync clients, for Snow Leopard.  The same principles will apply for Mail.app, provided it is a true ActiveSync client: simply point Mail.app at your CAS host.

One of the key reasons why Exchange adoption is so prolific is Public folders.  Public folders are likely on their way out, giving way to replacing the concept with Microsoft SharePoint.  I’m not going to say I love nor hate the idea, but in many institutions Public folders have been around for a long time, and while you likely will have until 2016 (worse case) to retire them, sometimes it takes as long to retire something as it took to build it in the first place…  In the meantime, many of the common tasks for managing Public folders are going to require you to hop into PowerShell, so keep that PowerShell book close at hand if you find you’re doing a lot of work with Public folder management (New-PublicFolder -name BillyBob).  Just something to keep in mind.

Finally, Exchange 2007 has a number of features for automatic archiving of data.  Entourage has no features for auto-archive.  So consider leveraging Exchange’s built in features, or as we’ve seen in some environments, having an out-of-band solution for managing archiving of mail to pst (or whatever format you prefer).

April 16th, 2009

Posted In: Mac OS X, Microsoft Exchange Server

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Incoming and outgoing mail are handled a bit differently from one another in Mail.app. This is helpful as you can have multiple outgoing accounts even if you only have one incoming accounts, useful if you move between a lot of different networks. 

To setup a new SMTP account, open the Accounts pane of the Mail.app preferences and choose Edit Server List… from the Outgoing Mail Server (SMTP): field. At the Server List screen click on the “+” icon and enter a description for the account. This can be anything to help the end user remember what this account is meant for. Then type in the name or IP address of the server in the Server Name: field. You can click on the Advanced tab here to customize the port, enable SSL or set the authentication type/parameters. Once you are satisfied with your settings, click on the OK button or click on the “+” sign to create another outgoing mail account.

Having multiple SMTP accounts can be confusing though. To remove an existing SMTP account, open the Accounts pane of the Mail.app preferences and choose Edit Server List… from the Outgoing Mail Server (SMTP): field. At the Server List screen click on the “-” icon while highlighting the account you would like to remove.

June 11th, 2007

Posted In: Mac OS X

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