What are your Entourage & Exchange pain points?

Someone recently asked me for my thoughts about today’s Entourage & Exchange pain points.

Below are my top 10 issues facing Entourage users working in Exchange environments. They are by no means in order of preference. I’d appreciate hearing what others think.


First, what didn’t I include?

  • Synchronization (or lack thereof) for tasks, notes and categories is a well-known topic and so those aren’t included.
  • Public folders and MAPI support have been de-emphasized in Exchange Server 2007 and so I chose not to include further comments about features that are going away.
  • I also left out a blanket statement of “Full feature parity with Outlook for Windows” simply because this is a top issues list.

Now, what are the significant issues that affect Entourage 2008 users who connect to Exchange Servers? What are the issues that may not be significant but act like small thorns when the user runs into them?
Pain points will mostly fall into two major categories:

  • Switchers who expect Entourage to act like Outlook
  • Mac users who need to interact with a Windows world
  1. Display names

    Microsoft should give Entourage users the ability to specify how display names appear for their contacts.
    Some companies use the format “Last, First” for display name while others use “First Last”. If an Entourage user receives a message with a “Last, First” display name and chooses to add the sender to his Contacts list (or Address Book) the names fall in the incorrect fields of the new Contact record.


    Pain Point: Outlook for Windows offers a feature to allow its user to enter field names correctly but display the full name in a few different ways. Entourage needs this ability so that sorting message lists by From or To is consistently sorting by “First Last” or “Last, First”.
    Pain Point: The Message –> Add to Address Book command and the contextual menu item Add Sender To Address Book need to be smart enough to know when a display name is in “Last, First” format and add the names correctly.

  2. Delegates can’t modify recurring meetings
    This pain point may have been addressed, I believe, with Exchange Server 2007 and Web Services; however, many companies and institutions are still running the older server version.
  3. Per this Microsoft KB article http://support.microsoft.com/kb/920134, complex calendaring is not supported with WebDAV clients.
    Pain Point:
    When an Outlook for Windows user is a delegate for an Entourage user and modifies a recurring appointment, the change is not reflected in Entourage.
  4. Sent items from ActiveSync are munged
    This is a known issue with Exchange Server 2003 but I’ve seen one user report he is still seeing this problem with Exchange Server 2007.
    Per this Microsoft KB article http://support.microsoft.com/kb/926521, header information for messages sent via ActiveSync is not displayed in Entourage. A simple one-line message sent via a mobile device:

    Can you please send me your notes from last week’s meeting?

    turns to gibberish when viewed in Entourage:

    In some cases, where message encoding is present, the content of the message will be completely unreadable, not just difficult to read.
    Pain Point: This problem is becoming more apparent with the iPhone 2.0 Update that uses ActiveSync.

  5. Sent Items aren’t syncing to Exchange Server
    This is a very common topic in the Microsoft Entourage newsgroup. My first suggestion to posters is to clear their Sent Items folder cache. However, this doesn’t always work. This newsgroup thread is indicative of many reports of this problem: http://groups.google.com/group/microsoft.public.mac.office.entourage/browse_thread/thread/4022f3d320aa92b.
    Pain Point: Users moving between two or more computers are affected. Some move between Entourage at work and Entourage at home, some move between Entourage and Outlook at work, and others move between Entourage and a mobile device. The Entourage Sent Items are essentially not getting backed up to the server and users can’t reference old mail messages unless they are on the sending machine.
  6. Entourage Sent Items aren’t appearing on Blackberry
    To the best of my knowledge this is a problem that RIM needs to fix. They have posted one KB article on their website http://www.blackberry.com/btsc/search.do?cmd=displayKC&docType=kc&externalId=KB05382, acknowledging:


    “When you send an email message from a Microsoft Entourage email client served by a Microsoft Exchange Server account associated with a BlackBerry Enterprise Server, the message does not appear on the BlackBerry smartphone.”

    The resolution:

    “This is a previously reported issue that has been escalated internally to our development team. No resolution time frame is currently available.”

    I’d like to see Microsoft approach RIM to help them resolve this long-standing issue.
    Pain Point: Sent items from Blackberry can not be referenced in Entourage.

  7. Entourage home users can’t easily access the GAL
    The LDAP Server setting in an Entourage account can not reach the necessary LDAP server when an Entourage user is outside his company network.
    I have an AppleScript freely available for download and another person has posted a GUI application that acts as a wrapper to the do OWA GAL search AppleScript command.
    If the functionality is built into Entourage then give it a GUI that the average user can discover and use.
    Pain Point: Although an AppleScript command exists and the community has contributed solutions for users to access that command, the novice user needs a built-in GUI means of accessing this feature. This feature is not discoverable.
  8. Cannot send new time meeting proposals
    This may be related to complex calendaring. Entourage users have no means, as Outlook for Windows users do, to receive an invitation and send a proposal for a new meeting time.
    Pain Point: Entourage users are limited to accepting, declining or asking the meeting organizer to resend or update the event to a new time. Negotiations are handled automatically in the Outlook for Windows world.
  9. Scheduling list truncates after about 20 invitees
    I recently found this reported in the Microsoft Entourage newsgroup.
    In a new calendar event invite more than 20 (say 30) attendees. View the Scheduling tab and scroll to the bottom. The list appears to stop after about 20 addresses and truncates the rest.
    Pain Point: Meeting organizers are unable to effectively view schedules of all attendees when the attendee list is longer than about 20.
  10. Contact groups don’t sync with Exchange
    An Entourage user can create local groups with his Contacts but he can’t replicate those groups to the Exchange Server.
    Pain Point: Groups and categories are two major methods for sorting and organizing items within Entourage. However, Exchange users have no ability to reproduce their sorts on other machines (Mac or Windows) because their sort criteria don’t get synchronized.
  11. Laptop users can’t easily switch between servers
    I encourage users to connect to a back-end Exchange Server while on their company network because it is a direct and faster connection. However, laptop users often select their OWA server for their server address because they move in and out of the network.
    Laptop users need the ability to select an alternate Exchange Server address so that they are always connecting optimally. An automated solution based on network location would be ideal.
    Pain Point: Using an external Outlook Web Access (OWA) address while on a company network can cause slow, sluggish syncing. It negatively impacts performance.

Like Steve Jobs, “and one more thing…”

  1. [Bonus!] No online viewing mode
    Outlook for Windows offers its users the ability to view their mail without caching it locally to the computer. Entourage currently operates in permanent “Cached Exchange Mode” only. Users need the ability to do both.
    Pain Point: Some high security companies are requiring that their E-mail clients not store any mail data locally on machines. Entourage currently cannot comply with this requirement. This should be enforceable by a company administrator.
    Pain Point: Employees may “hotel” at different desks from day to day. Syncing a large mailbox on a new machine each day can be time-consuming and waste disk space.
    Pain Point: Caching all account data can bog down a slow network or dial-up connection, especially accounts with many attachments.

I neglected to mention this the first time…

  1. [Double Bonus!] Can’t use stand-alone Entourage with Home & Student
    With the transition from Office 2004 Student & Teacher to Office 2008 Home & Student, Exchange support was removed. However, Microsoft has made Entourage 2008 with Exchange Server support available as a stand-alone product for hosting companies to distribute to their clients.
    Customers who have purchased Office 2008 Home & Student have reported that they are unable to install the stand-alone Entourage 2008 with Exchange Support without compromising their original Office installation.
    Pain Point: These two Microsoft products, Office 2008 Home & Student and stand-alone Entourage 2008, conflict with each other forcing the customer to have to choose between one or the other.

And later, I was reminded of this…

  1. [An unprecedented Triple Bonus!] Read, Reply and Forward statuses do not sync
    Between Outlook, Exchange and Outlook Web Access (OWA) the Read, Reply and Forward status arrows sync but Entourage does not sync this data with Exchange.
    Similarly, Reminder statuses sync between Outlook and OWA but not with Entourage. If I’m away from my desk and snooze a Reminder on my iPhone for “30 Minutes Before Start” then that should be reflected in Entourage when I return to my desk.
    Pain Point: Users moving between two or more computers, where one is running Entourage, have no visual cue as to which messages they’ve already processed on other machines.

Additional Notes

  • I haven’t mentioned that Entourage needs the ability to at minimum import PST files because I don’t see this as an Exchange pain point. However, it is still the number one pain point for switchers moving from Outlook to Entourage. And I suspect these switchers with PST files are mostly in Exchange environments.
  • These pain points exclude those that Microsoft know very well already: Tasks/Notes syncing with Exchange as well as Categories syncing with Exchange.
  • I posted a blog entry on Exchange Server needs. The comments may be of interest:

    Prioritize your Exchange needs!

  • Since compiling this list an unofficial method for installing the stand-alone version of Entourage 2008 with Office 2008 Home & Student was posted on this blog:

    Install Standalone version of Entourage from Exchange Email Provider with the Home & Student Version

  • Also since compiling this list I developed a work around to allow Entourage users to view ActiveSync Sent Items:

    Use AppleScript to read ActiveSync Sent Items in Entourage

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16 comments to What are your Entourage & Exchange pain points?

  • How about – searching emails in Inbox for ‘From contains’ only searches for the text typed in the visible sender’s address. Example: someone@domain.com sends email but his sender address is shown as John Doe. If I searched for “domain.com” I expect his emails to be shown, but no, they don’t. All other email programs I’ve tried will search on the full ‘from’ header field, not just the visible part. Also, there is no ‘search everywhere’ option. I don’t want to waste space by having Spotlight index all my messages, so the search functionality is severely crippled.
    Nice post, let’s hope the Mac BU listens!

  • Eric Benfer

    I already know the answer to this, but…
    Why don’t they just write Outlook for OS X?
    If they choose not to do that then release the Outlook 2001 for Mac code to open source. (Ha ha ha, I cannot even type that with a strait face.)
    By the way the answer is because Microsoft hates ME. They want to cause ME more problems and headaches.

  • I have one more particular pain point. In Outlook, I was able to receive an email and convert that email into a meeting invitation. The contents of the email were incorporated into the meeting text. This was a great way to take a request and turn it into an opportunity to pull a few people together to address an issue. Now I have to switch to my calendar view, create a new event, add the sender of the email as an invitee, and copy and past the email body into it.

  • There is also the issue of ‘optional invitees’. In Entourage when you invite people to a meeting and you want to show that not all are required and some are optional, you can’t. My Entourage users find this a bit frustrating.

  • michael

    I gave up on Entourage. It’s always felt thrown together and has never been up to par with Outlook.
    So…I run good ol’ XP with Outlook on VMWare.
    The whole “Sent Items” issue with ActiveSync has been there for years and the fact that it’s still not been resolved is ridiculous.

  • No access to Deleted Item Recovery. Note that this feature is also not available via OWA Light, so Mac users are completely out of luck on this.

  • John Wetter

    Great List! I think if your list could at least be addressed, a lot of people would let up on the ‘make Outlook for mac’ talk. I don’t think that is particularly constructive at this point. I do think we need to clearly tell the MacBU what items are unacceptable to be left out of Entourage. I think your list addresses almost everything that is a ‘daily’ annoyance.
    I’d go a step further to re-title this article to: “Entourage is not an acceptable Exchange client due to these well known issues:”
    I think the tasks/notes syncing and #13 are huge.

  • For point #10, I believe NetworkLocation 3 has an optional Entourage plugin that will adjust server settings when you switch locations — I haven’t tried it yet, though.

  • Another item: it would be nice if Entourage’s implementation of Autodiscover actually worked. Our Outlook 2007 clients have no problems with it.

  • Patrick Kuras

    PST support (or something like it) is a biggie, and it does directly relate to Exchange users – when a user’s mailbox reaches its quota, or if the user just wants to clean things out a bit, it’s necessary to be able to move messages into a locally-stored archive file. In Outlook, this is trivial. In Entourage, it’s impossible. And minimal PST import capability is not sufficient.
    I don’t strictly NEED it to be a PST file per se (although that would make a lot of sense – why reinvent the wheel and put up another Mac-Windows wall?), but SOME kind of local information store, with the ability to attach to more than one at a time, is essential.
    Also, this local store absolutely MUST be indexable by Spotlight. That’s what makes the local store useful.

  • Reuven

    When receiving mails from Outlook users, somc of them contain a winmail.dat that can’t be read by Exchange. It’s very annoying and it’s particularly bad since both are Microsoft applications. I tried the Tech Support and they seem to be helpless. The only suggestion was to ask Outlook users to make changes to their configuration, which is out of question.

  • shawn bailey

    The fact that my Entourage won’t stay connected to the Exchange server for more than 30 minutes whether I’m home or in the office.
    There is some bug revolving around something in the junk-email folder. If messages have some particular mishmash of characters or whatnot, it blows up the connection. I’ve searched for this and it appears that the MS patch is server side only. Our email provider only supports Outlook and MS, no Macs or Entourage.
    My only workaround is to login to OWA and simply navigate to the junk email box and make sure nothing is there. If there isn’t, it usually reconnects when I restart. Still, what a damn waste of my time. I can’t wait for OS X 10.6…I’ll never open Outlook or Entourage again!

  • jonesey

    I have reported a number of Exchange/Entourage bugs via the Microsoft Feedback web page. I hope the MacBU reads them. This one is the worst one I can remember offhand:
    Some folders simply do not sync, and there is no error message. I imported all of my folders from a local set of mbox files (made by Eudora), and some of them had broken messages in them. They look fine on my computer, but if I go into OWA, there are no messages, or just a few messages, in some of the folders. Entourage does not give any indication that there is a problem. It should be able to do a simple message count on the local side and the server side and let me know that there was a sync error.

  • jamie

    Hi there… is there a solution to your problem 12.
    i have this problem and i have been looking for an fix.
    thanks.
    jamie

  • Mike Alev

    When we delete mails in Entourage it will not sync in Exchange server 2003 meaning in BB, webmail or in Outlook.
    OS is 10.5.7 and Entourage 2008 with latest updates.