Bugs & Fixes: Microsoft Outlook annoyances

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I’ve been using Outlook 2011 as my mail program since Microsoft released it as the replacement for Entourage last year. Overall, the transition from Entourage has been a smooth one. Outlook does have several quirks and omissions, however, that bother me on an almost daily basis. What is especially irritating about these quirks is that Entourage handled the same situations with no problem—making Outlook feel more like a downgrade than an upgrade. A few of the issues (such as the lack of a Resend command) have been remedied in subsequent updates to Outlook. But not all. Here are three that remain:

Reply All In Entourage, if you selected to Reply to a message and later realized that you wanted to hit Reply All instead, the shift was easy to accomplish. You just clicked the “Reply to all” action, located below the message’s toolbar, and the switch was made.

Entourage’s “Reply to all” option no longer exists in Outlook

In Outlook, this “Reply to all” option is gone. Instead, if you want to go from Reply to Reply All, you have to discard the message draft and start over with an entirely new message, this time beginning by selecting Reply All rather than Reply from the received message’s toolbar (or from the Message menu). If you’ve already finished writing your email by the time you make this discovery, you’ll have to copy/paste your work to the new message. Annoying.

I’ve read that Microsoft plans to return this feature in a future Outlook update. I certainly hope so.

Junk Mail In Entourage, if you selected “This is not junk e-mail” for a message currently in the Junk E-mail folder, a window popped up that gave you the option to “Classify all messages sent from the sender’s domain as ‘not junk.’”

This option was a convenient way to prevent subsequent messages from the same sender from being routed to Junk E-mail but without having to add the sender to your Address Book. Unfortunately, this option no longer exists in Outlook. In fact, when you select “Not Junk” for a message in Outlook, you have no options at all. The message is immediately moved to your Inbox; that’s it.

The window that appears in Entourage if you select “This is not junk e-mail.”

According to Microsoft Help, the way to prevent subsequent messages from a particular sender winding up as junk is to manually add the sender to your Address Book via the Message -> Sender -> Add to Contacts command. Not good.

Attachments In Entourage, when you opened a window for a new message, an Attachments section was included in the messages header (just below the Subject text box). If you dragged a file from the Finder to anywhere into the header region, the file was added to the message as an attachment. Perfect.

With Outlook, an Attachments section does not appear by default. It appears only after you add an attachment. By itself, this would be a trivial change—if you could still add an attachment by dragging a file. The problem is that, too often, dragging fails to work.

After testing out various hypotheses, I have a decent handle on most (but not all) of the causes of this bug—and how to work-around them:

• You’ll have better luck if Outlook is the active application when you drag. That is, to drag a file from the Finder to Outlook, first click on the message in Outlook. Then click-drag on the file without allowing the Finder to become the active application (yes, this is possible).

• Locate the pointer of the dragged file in the message’s header region so that it is between text boxes, not inside a text box—as illustrated in the figures below.

Outlook rejects an attachment when the tip of the pointer is in a text box.

Outlook accepts the file as an attachment (indicated by the + icon) when the pointer’s tip is outside any text box. But not always.

Alternatively, if you drag the file to the body region of the message window, this may also work. However, if the file is a graphic, the image will be appended to the text rather than added as an attachment. This is probably not what you want.

• If you have a dual monitor set-up, ideally have the message window and the desired attachment file visible in the same display. I’ve found that dragging a file across displays reduces the odds of success.

• Upgrade to Lion. I’m not absolutely certain, but it seems that I am having greater success with attachments in Outlook when running Apple’s latest OS X version.

The remaining problem is that, even when using all of these tips, the attachment process is still inconsistent. Especially in Snow Leopard, it fails to work for me at least 25% of the time, for reasons I cannot yet determine. Very annoying.

The only sure work-around is to give up on dragging and instead select the file via an Open dialog. To do this, either select the Attach command from the message window’s toolbar or use Command-E (Draft -> Attachments -> Add). My quarrel with this work-around is that dragging a file, if it actually succeeded, is almost always quicker and is what I would prefer.

Bottom line In case you’re wondering, the main reason I have preferred Entourage (and have thus far stuck with Outlook) is that I like Microsoft’s integrated approach (with mail, calendar and address book all in one app). As it turns out, I now use BusyCal for my calendar and OS X’s Address Book for my contact database—because this makes for smoother syncing with my iOS devices. With the advantage of integration largely gone for me, it may be time to shift from Outlook to Mac OS X’s Mail. I just need to overcome my inertia.

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At a Glance
  • Pros

    • New interface makes many tasks easier to access
    • Improved Exchange support
    • Faster than Entourage
    • Redesigned AppleScript dictionary
    • No longer reliant on a single database
    • Better support for Time Machine and Portable Home Directory Sync
    • Redesigned preferences make setting up the application easier
    • UI more compatible with Outlook on Windows


    • Assorted 1.0 bugs
    • AppleScript implementation holes mar improvements to AppleScript Dictionary
    • Exchange support requires Exchange Web Services
    • Exchange 2003 and earlier not supported
    • Exchange support limited to what EWS allows
    • Time Machine limitations
    • UI changes hardest on existing Entourage users
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