Optimize Entourage to better work with Exchange

Why is connecting Entourage to Exchange is so tricky sometimes? Mail might work but public folders don’t appear. Maybe the Global Address List (GAL) just doesn’t work. Or maybe getting new messages is just very slooow.
The solutions to these problems lie with knowing when to use the right server, knowing how Entourage talks with Exchange and tweaking other software to reduce interference.

Where am I and where is my Exchange Server?

This is the most important question to ask yourself because it defines which servers you should be using.

Does your company have its own Exchange Server and are you at work connecting to your company’s network? Then you are inside your Exchange Server’s network. You have direct connectivity.
Does your company have a hosted Exchange Server? Then you are outside the Exchange Server’s network. You must pass through your own company network, hop on the Internet and then connect to your host’s network to get to your Exchange Server. You do not have direct connectivity.
Are you at home connecting to your Exchange Server? Then you are outside the Exchange Server’s network. Just like a hosted Exchange Server, you must connect to your home ISP, travel across the Internet and connect to your company’s network to get to your server. You do not have direct connectivity.

Are you In or are you Out?

If you are inside the network with your Exchange Server then you can take full advantage of Entourage’s Exchange features. You can:

  • Use Kerberos authentication (Entourage 2008 only)
  • Send and receive mail and calendar events
  • Use Exchange delegations
  • Use shared inbox, calendar and contacts
  • Check free/busy schedules of others
  • Use public folders
  • Browse the GAL

If you are outside the network of your Exchange Server then you can take only partial advantage of Entourage’s Exchange features. You can:

  • Send and receive mail and calendar events
  • Use Exchange delegations
  • Use shared inbox, calendar and contacts
  • Check free/busy schedules of others
  • Use public folders

Kerberos authentication and browsing the GAL require direct access to your company network because they use servers other than the Exchange Server itself.

Log in to your account using Outlook for Windows.

Locate the Outlook icon in the System Tray near the clock.

Hold the Control key and right-click the Outlook icon.

Select Connection Status… from the contextual menu.

What address should I be using with Exchange?

An Exchange account in Entourage has three server address fields and you could potentially be using up to three different servers, each with different functions.

  • Exchange server: Responsible for your mail, calendar and for delegation
  • Public folders server: Responsible for public folders as well as your free/busy schedule
  • LDAP server: Allows you to browse the GAL but only while you’re in the same network as your Exchange Server

If you are in the same network as the Exchange Server then you have access to every server and can use all of Entourage’s Exchange features. You’ll use the addresses that have been provided you by your administrator. (Some Windows-centric administrators aren’t too helpful to Mac users. Use the instructions in the sidebar to learn how to use Outlook on Windows to find your server addresses.)

The server that you’ll use here is called a back-end server. This is where your account resides. Follow my instructions for Connecting Entourage to an Exchange Server at work.

However, if you are outside your Exchange Server’s network then you have only one address, which can be used for both your Exchange server and Public folders server but not your LDAP server. This address is an Outlook Web Access (OWA) or webmail address.

OWA servers are front-end servers. They do not store mailboxes but instead act as connectors between Internet users and back-end servers where the mailboxes really exist. Follow my instructions for Connecting Entourage to an Exchange Server from Home or for use with a hosted Exchange Server.

I’m on a laptop. Can I use my OWA address to connect inside and outside? It appears to be working.

In many cases you can but it may not be very efficient. I don’t recommend using your OWA address while inside the Exchange Server’s network because that often means you’re going through your company’s proxy server to get to the Internet and then coming back into your network to get to your mail. Firewalls and virus scanners can get into the mix and you’re adding at minimum two hops (two servers) between Entourage and your mailbox.
Entourage should sync about every minute with your Exchange Server and then stop. It should never continually sync, which is a symptom of using an OWA address inside the network. This not only makes Entourage sluggish but it also means that mail is not arriving as quickly as it should.

To work around the problem of switching server addresses I’ve provided instructions for using AppleScript with Entourage to automatically switch an Exchange account’s server addresses based on whether or not it determines Entourage is connecting from inside or outside the Exchange Server’s network.

Is that all I can do to get better performance?

Not at all.

Keep your Inbox as small as possible

How big is your message store? In Entourage you can right-click your Exchange account in the folder list and select Folder Properties –> Storage.

Pay particular attention to the size of your Inbox because this is kept in sync more often than other folders. Entourage 2004 sp2 improved sync speeds by giving higher priority to certain special folders such as the Inbox. It will sync more often whereas regular mail folders will sync less often. If you have any sub-folders in your Inbox then move them out to a different set of folders at the same level as your Inbox.

Also, keep in mind that Entourage Schedules do not affect Exchange account syncing. You can disable your Send & Receive All schedule if you only have an Exchange account.

User Headers only mode

Where is your Exchange Server on your network in relation to Entourage? Are they separated by fairly fast network links or slow network links?

For my company’s graphics users in New York City who access a shared mailbox on our Exchange Servers in Saint Paul across a slower-than-T1 link I have them put Entourage into Headers only mode. In Entourage

  1. Select Tools –> Accounts…
  2. Double-click your Exchange account
  3. Under the Options tab set “Partially receive messages over” to “9999 KB always”.

This sounds counter-intuitive but that’s how it works. You’ll notice that the account displayed in your folder list will include (Headers Only) at the end of its name. Only the subjects and dates will be downloaded until the message is actually previewed or opened.

Exclude the Entourage database from antivirus and Spotlight scanning

Make sure that Spotlight preferences and any antivirus software such as Symantec Antivirus are excluding the “~/Documents/Microsoft User Data” folder from their scanning where ” ~ ” is your home folder. Spotlight preferences are in the System Preferences and SAV preferences should be there as well. If you don’t have SAV appearing in your System Preferences then download the Auto-Protect preference pane and Symantec QuickMenu from Symantec.

If you have other suggestions or questions about improving performance between Entourage and Exchange, please let me know. Other Exchange questions should be directed to the Microsoft newsgroup for Entourage
The newsgroups have been closed. Ask on Microsoft Product Forums

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30 comments to Optimize Entourage to better work with Exchange

  • Boris Germashev

    Hello,
    I would appreciate any hint or an idea. While connecting to Exchange at work – the Assistant gets all settings automatically. I can send email. I’m also getting whatever is on Exchnage synchronized to my Entourage. However the sync is uni-directional. For example, new Calendar entries are not propagated from Entourage up to Exchange. Also if I sent an email, Entourage cannot sync the new item in Sent folder with Exchange.
    Thank you in advance for any ideas.
    Boris.

  • Hi Boris!
    No different settings are responsible for syncing up to the server than down from the server. This sounds like a problem with the server or your network.
    Test what happens when you connect via OWA using the same server address you’re using in Entourage. For example, if you’re Entourage server is “server.domain.com” then open Safari on the same machine and enter “http://server.domain.com/exchange”. Try creating a new mail message there and see if you’re able to send.
    Diane has posted a little detail about using TCPflow here
    http://www.entourage.mvps.org/troubleshoot/tcpflow.html
    You can use that to see what messages are being sent between you and the server.

  • Mark Ungewitter

    Hi William,
    My name is Mark Ungewitter and I work for a company called the 7th art. The partners contacted myself and my IT manager looking for a specific sync solution. What they want to accomplish is data-basing all of the client contacts for the company as well as employees and syncing the database to our exchange server so that the information would be available to retrieve off company of blackberry devices. Could this easily be done using a shared contact list through Entourage? If so, How would I go about doing so, and if not, do you have any other ideas or solutions. Thanks in advance.
    -Mark

  • Michael Reeves

    Strange goings on… I have Entourage 08 and it has worked flawlessly for 2 months. Suddenly, I’m not receiving e-mail from our company’s MS Exchange server. I can even pinpoint the last e-mail I got/didn’t get. I’ve restarted, reviewed the settings, nothing is working. All of the e-mail is accessible via our website, which I can move to my draft folder, then I go into Entourage and manually move it to my inbox. I think the only thing I can do is reinstall, but I’m afraid I’m going to lose my settings. Our IS says nothing has changed from their side, so it sounds to me that Entourage is broken. Any suggestions? Thanks so much.

  • Wasif Ahmed

    i have mac pro system mail working Entourage not working
    please ……….
    =============================================================
    Added comment: You did not provide enough info in your request to offer help. The best place to get help with a problem is the Entourage newsgroup.
    How to subscribe to the MSFT newsgroups
    You will need to provide details. See this page for info you need to include:
    How to Report a Problem
    Diane Ross

  • I also have strange goings on and hope someone can help. I use an Exchange Server account to connect to my office system (Entourage 08) and it was working fine until recently when it now no longer deletes Inbox emails on the office server when I delete them in Entourage. It syncs everything else fine (Junk E-mail, for instance and everything else) but it no longer deletes the Inbox emails. I don’t know what to do and checked my settings as best I can. Suggestions?

  • Hi Folks!
    Just wanted to inject a quick comment that personal help questions need to be asked in the Microsoft Entourage newsgroup found here:
    http://groups.google.com/group/microsoft.public.mac.office.entourage
    While we’d like to be able to answer all questions here, this is not a forum and we don’t have the resources to respond to individual help questions.
    Thanks for your understanding! bill

  • Mattias Bryneson

    Hi,
    Can Entourage 2008 connect to an Exchange proxy server? In Outlook 2003 this a separate connection option with specific authentication.
    Thanks,
    Mattias

  • ConradR

    Hi
    I could really use some help on an issue.
    Does anyone else have the problem with reply symbols not syncing? If I reply on my exchange account from one computer the email shows a symbol indicating that I have replied.
    But Entourage does not sync that fact through Exchange. So any other computer that accesses my Exchange emails does not recognise that I have already replied to the email.
    It means that if you work from home,and answer a load of emails, when you access the emails in your office it looks as if you have never replied to them.
    Its infuriating.
    Am I missing something?
    Thanks.

  • William M. Smith

    You’re not missing anything. Entourage does not sync the Reply and Forward status arrows.
    If you test between Outlook and Outlook Web Access (OWA) then you’ll see that they do synchronize and since Entourage connects via WebDAV (the same mechanism as OWA) then I’d hazard a guess that the potential is there, just not implemented.

  • ConradR

    Thanks very much for the reply. Really appreciate it.
    It seems like a really unpleasant thing for Microsoft to have done.
    I understand that Microsoft might not want to put the same time and effort into Entourage as Outlook, but to deliberately disable an important feature present on any other email client is just malicious.
    Its almost hard to believe they would be that unpleasant to customers.
    Presumably no one from Microsoft will explain what is going on, on this blog.
    Does anyone have a good workaround, or do we just have to pretend that forward and reply status arrows don’t matter?
    Thanks again for the quick reply.

  • William M. Smith

    I would strongly dispute that Microsoft deliberately disabled this feature. Was this even present in Entourage 2004? I don’t recall.
    If it was in Entourage 2004 then it was left out of 2008 by mistake just like the ability to edit messages. That has been acknowledged by Microsoft as something taken out temporarily to troubleshoot a problem and simply forgotten. By the time they realized the problem they decided not to put it back in because they were too close to RTM to risk making a change.
    If syncing the status arrows has never been in Entourage then I’d say it’s “By Design #2”.
    One of the developers explained to a few of us that things are either bugs or by design. A bug is a feature that’s not working as expected. But some bug reports can be marked as “by design”. That can mean either “[By Design #1] they intended for it to work that way (It’s a feature not a bug!) or [By Design #2] they never thought about it working the way you expect.
    The best suggestion I can give is to let Microsoft know how important this feature is to you by using the Help –> Send Feedback mechanism in any Office application. I doubt seriously that they omitted this on purpose. They could think of far better methods to be malicious.

  • ConradR

    William, thanks again for your reply. I will let them know, as you suggest.
    But I have now found out that it was not in 2004 and despite many people notifying them of how important it is, it was not put in 2008.
    Its hard to imagine a “By Design #2” situation – why would anyone think that a notification like that should not be synced? As you point out, its really easy to do and every other email service does that. It makes no sense. Its very hard to believe it is accidental.
    Just a single word from Microsoft explaining why it wasnt sorted out in 2008 and when it will be fixed, would be infinitely more reassuring than the conspicuous silence and the prospect of waiting another 4 years only to be disappointed.
    In the absence of that i find it hard to be as forgiving as you are.
    Thanks.

  • JohnT

    Is there a way to re-order the way the Contacts and GAL are displayed in the Compose windows?
    For example, when I type a name, it will show list of addresses from Contacts or MRU before GAL.
    Is there a way to display GAL first?

  • William M. Smith

    Interesting question.
    The order can not be rearranged but it is in order of what should be the smallest to the largest group as well as fastest to slowest to search. You’ll notice that all three lists don’t always appear simultaneously but rather they appear in order of MRU list (quickest), Contacts (slower) and GAL (slowest).
    The MRU list should often be the shortest list when matching names because you’ve already pulled names from your Contacts or GAL, basically filtering out addresses you haven’t sent to already. If you don’t use the MRU list then you can disable it in Entourage menu –> Preferences… –> Mail & News Preferences –> Compose –> Recent Addresses. That will shorten your list by one.
    Your Contacts list should be much shorter than the GAL and takes far less time to search than the GAL, which makes it a more logical “second” choice in the list. And the GAL will usually take a few seconds to populate. If you’re not finding an exact match in your MRU or Contacts as you type to complete a name then it will be the only list you see with any addresses.
    I’m sure what I’ve said above isn’t really what you’re wanting to hear but I think the ordering is logically done. Even if it could be re-ordered I’m not sure doing so would be efficient.

  • Christine L

    I am having trouble with the send/receive feature in Entourage (ver. 11.4). I’m a home user and it isn’t going out to my ISP and retrieving my messages. I have to manually pull down the Send & Receive tab on the menu bar. I’ve edited the schedule to this:
    Send & Receive All
    When:
    Repeating Schedule Every 2 Minutes
    At Startup
    Only if connected is checked
    Action
    Receive Mail from Christine’s E-mail acct
    Dial Up options: Stay connected
    Am I missing something, it is driving me nuts! Also, I’m on a MAC system OS X.
    Thanks,
    Christine

  • Diane Ross

    Your schedule only runs at startup. Remove this Occurrence. I also suggest a longer period of time between downloads. Two minutes can overlap and cause problems. I also do not like to download when Entourage is starting up. If there are any problems with an email, it can cause Entourage not to open making it harder to deal with the problem.
    Under the Receive Mail in the Action part, did you select your account?

  • Josh Moreton

    Hi guys,
    I know this is not a forum for asking questions, but I am at my wits end.
    we are running an exchange server2k7 system and have a few users on macs, some leopard, some tigers and entourage 2k8 was installed recently.
    Now it just will not sync with our exchange server, it can auto detect the settings, or we can manually input them as per the microsoft instructions, and various other instructional documents found on the internet (including http://entourage.mvps.org/exchange/exchangeatwork.html) but no luck.
    I have read many websites and posts saying entourage does not support OWA, and that there are many others out there who cannot get entourage 2k8 to connect to an exchange 2k7 system, so can anyone help here??
    If you want to contact me, its josh.moreton@cbi.org.uk
    thanks,
    Josh Moreton

  • Hi, William. Thank you so much for this post! It greatly helps in dealing with Microsoft’s rather mystifying (if I am generous and assume no deliberate hobbling to make Windows seem like the more attractive client platform) decision to not implement automatic discovery of the LDAP and Public Folders servers as occurs with Outlook.
    One thing that’s worth mentioning is that Exchange apparently has a feature where if a group of users are being moved to a different Exchange server, their Outlook clients can be automatically notified and their profiles will be automatically updated to point to the new server(s), without the administrators needing any administrative access to the client machines.
    Entourage apparently does not support this, so when my account got moved recently, Outlook auto-corrected itself but Entourage is still pointing at the old servers.
    This leads me to a question. With my old set of servers, there was only one server per function (Mail, Directory, and Public Folders). In the new setup, there are at least two servers listed of each type. I’m thinking this is to enable failover (although I’m not quite sure what to make of the *three* Public Folders servers listed).
    It appears that Entourage does not support entering multiple servers into those fields. They are all labeled “[…] server:”, not “servers:”, and I tried putting multiple servers (separated by commas, then semicolons, then spaces) into “Public folders server:”, but Entourage would just complain that it couldn’t find the server.
    So, do you know which of the multiple servers should be entered in each category? Is the first one listed of each type in the Exchange Server Connection Status dialog the primary one? Or is there no significant to the order multiple servers of the same type appear in that?
    I guess if this setup is indeed to enable failover, then if there’s a failure, Outlook clients will keep working while Entourage fails, which is rather unfortunate.

  • William M. Smith

    Hi Dan!
    Actually, Entourage 2008 (starting with SP1) and Exchange Server 2007 SP1 or later do support Autodiscover. This feature not only provides initial setup of Entourage but also server redirection. As with any discovery service your network must be properly configured to respond to these requests (that means good DNS setup). And this only supports connecting to back-end servers not front-end Outlook Web Access (OWA) servers.
    Be sure to read White Paper: Exchange 2007 Autodiscover Service and search for Autodiscover on the IT Pros website for Office for Mac.
    I’d appreciate anyone’s experiences with using these services with Entourage 2008.
    You are correct that Entourage does not support multiple server addresses. However, with enterprise support becoming more of a focus for Office for Mac I suspect we’ll be seeing lots of Exchange improvements.

  • Steve

    I do have a question .. I have a MAC entourage user who seems to have a email issue.
    Yesterday at 5PM ES she received her last email from the exchange server …
    She has log into outlook web access and she see’s all her mail that seems to be missing in Entourage- I have checked her mail file in a outlook 2007 client and the mail is all fine there to.
    Why did mail stop flowing to entourage – she is connected fine and can send mail and the entourage client says updating in box like it should be but seems to never pull down the new mail.
    She is working off web mail right now ..
    Any thoughts IT guy tossed into the mac world

  • If you see this in just one or a handful of folders then right-click or Control-click that folder, select Folder Properties and click the Empty button to empty the cache. You can also select the account itself and empty the cache for all of your folders.

  • If I configure GAL in Entourage 2008, vers. 12.1.7, it sometimes hangs for several minutes (spinner) while looking up a contact in the GAL. Any idea? I’m in-network, but am using https://owa.uta.edu which is being routed through a Netscaler to access Exchange.

  • You’ll want to re-read the section in my post about “Are you in or are you out?” You cannot access the GAL through an OWA server with Entourage 12.1.7.
    However, if you have an Exchange Server 2007 server then you may be interested in the Entourage for Exchange Web Services beta. Entourage for EWS will support GAL lookups through OWA.
    http://blog.entourage.mvps.org/2009/01/what_does_entourage_for_exchange_web_services_mean_for_you.html

  • Cris

    can Entourage 2008 be configured to work on an OWA Exchange website that requires a smart card for authentication?

  • @Cris
    Sorry, no, Entourage has no ability to deal with third party security systems.

  • Tammy Moran

    I just go the new Entourage 2008 and connected to the Exchange Server and everything seems to be working except the tasks. The problem that I am having is when I get a task from someone else in the company that is using Outlook the task doesn’t save. Does this not work from Outlook to Entourage. Also when I set up a task it doesn’t save it in the tasks at all it is black but when I look at it from the calendar and click on to do list they show up there. I am just confused.

  • No, this does not work.
    Entourage does not support exchanging tasks with other users and only the Web Services Edition of Entourage (for use with Exchange Server 2007) supports syncing tasks with the server.
    Also, Tasks are not To Do items. Check under the To Do section for tasks you might be missing.
    If you have further questions, be sure to post them to the Entourage newsgroup:
    http://groups.google.com/group/microsoft.public.mac.office.entourage
    or to our YouTalk mailing list:
    http://www.entourage.mvps.org/support_options/list.html

  • Chris Dyer

    Hi, I could really use some help on a licensing snafu.
    I have Office 2008 Student/Home edition installed in Mac OSX. Obviously, the Entourage version in this suite does not support MS Exchange. However, I also subscribe to a hosted Exchange email service which provides a free copy of Exchange enabled Entourage with my account.
    Unfortunately, when I install it, the key/license for the Student/Home edition of Office seems to over-ride the full Entourage version provided by my email service and therefore prevents me using Exchange.
    I’ve tried uninstalling Office and installing the full Entourage on its own first, but as soon as I re-install Office it over-rides the license again with the student/home non-exchange version. I’ve also tried deselecting “entourage” during the installation of Office.
    Any ideas how I can get around this?
    Thanks.
    PS: I’d prefer not to use Mac Mail with Exchange as it has issues.