My wish for OS X Mail


Here’s a wish for Apple’s Mail. When I’m creating a rule that depends on an address, Mail should live-search my Contacts as I type in this field. Instead it does nothing. If I’m working with an unfamiliar address, I must abandon the rule creation, find the address, copy it and then start over.

It’s not “your children have died in a fire,” but still irksome.

Daily Tip: Find draft emails quickly on iPhone

Here’s a trick I found quite by accident. You can jump directly to a list of your draft emails in Mail for iPhone by pressing and holding the compose button:


Jus hold your finger down and this list pops up. Tap any one to jump right to it. I just happend to press and hold the compose button and up popped the drafts list. Excellent.

This post is part is one of 31 tech tips I published in March, 2013You’ll find the rest here.

Daily tip: Disable iOS Mail sounds


One of my most effective productivity tips [1. You could also, as reader Kit Pierce points out, switch it to manual check.] is to disable email alert sounds. Few things are as distracting and demanding as that little beep. Fortunately, it’s easy to switch them off on your iPhone, iPad or iPod touch. Here’s how.

  1. Open Settings.
  2. Tap Sounds.
  3. Tap New Mail. A new screen appears. Select None.

That’s it. Now you can keep your push mail account active without hearing that little “Ping!” every time a new message arrives. While we’re at it, let’s disable Mail notifications, too:

  1. Open Settings.
  2. Tap Notifications.
  3. Tap the appropriate email account, then move the slider to the Off position.

That’s it! No more pestering sounds or messages every time a new email arrives.

This post is part is one of 31 tech tips I published in March, 2013You’ll find the rest here.

iCloud Mail, hover states and link cursors [Updated]

Vincent Gosselin writes about the lack of a hover state or link cursor in iCloud’s Mail web app:

“iCloud web apps are used by desktop users. You can’t log in to these apps within Safari using an iOS device. Therefore, mouses and trackpads are the main inputs.

What’s the most useful interactive feedback you can provide to a mouse or trackpad user?

A hover state and a link cursor.

Yet, they are almost nowhere to be seen in the apps.

All buttons have an active (pressed) state. They prioritized active states over hover states, as if the iOS users were the main audience for these web apps.

They’re not.”

I noticed this, too, but still knew that those elements were clickable. Of course, I’m not the service’s main audience, and I see how a home user might consider those elements static. Vincent mocked up a proposed hover state and link cursor for the Mail web app that I’ll let you check out.

Update: Louie Mantia points out the web app’s similarity to the desktop version.

Add custom flag labels to Mail in Lion

Mail, Apple’s email client that ships with Mac OS X Lion, features colored flags that can be used to highlight and group messages. There are seven to choose from: Red, Orange, Yellow, Green, Blue, Purple and Grey. To assign a flag to a message, simply open the message and click the flag button in the toolbar. By default it will apply the currently-displayed color to that message. To select a different color, click the black disclosure triangle on the right (see below).

That’s great, but labels like “Red” and “Green” aren’t very descriptive. It would be better to apply a custom label, like “Soccer” or “Budget.” Fortunately, you can! Here’s how.

First, you must assign at least two different flags to (at least) two messages. Once that’s done, a “Reminders” area will appear among the mailboxes list on the left [1. If it’s not there already.]. Click the disclosure triangle to reveal a list of the message you’ve flagged (see below).

Next, right-click (or Control-click) on one of the flags and select “Rename Mailbox…” from the contextual menu. The flag’s name will then be ready to accept your edit! Type the new name, hit Return and you’re done.

Note that the message count depicted next to my green flag above (“4”) represents the number of messages with a green flag, not their read/unread state.

More on mail rules

Ben Brooks was kind enough to respond [2. Incidentally, this is the type of conversation between bloggers that I enjoy. I’m much happier to write a thoughtful post than drop a knee-jerk comment on Ben’s blog, and vice versa.] to my post on email management which referenced his. Ben:

“I have great respect for the fact that Dave Caolo reads each email, treating them all the same, but that doesn’t and won’t work for me. Nor do I think I would want to do that, when you send me an email that I am copied in on along with 50 other people, without even referencing me in the email, here is what crosses through my mind:

‘This person clearly just wants to show how important they are by wasting 50 peoples time all at once. Bastard.'”

The feeling is mutual, Ben. I want to reinforce that I wasn’t suggesting my inbox management routine is The One True Way. I quite like Ben’s clever Mail rules, which is why I shared them with TUAW’s readers. Whatever trusted system works for you is the one you should use.

My email management philosophy is this:

Stuff > [Process] > Trusted System > Action

“Process” is the variable. However you define it, as long as it promotes efficient progress through the final steps, is fine with me.

Apple’s updated Mail

After a short public beta (just over one month), Apple updated its Mail web app for MobileMe customers last week. The new features are now available to everyone, plus a few that weren’t a part of the beta. The major changes include a new UI, the addition of rules, one-click archiving and support for external email addresses. Here’s what’s changed and what we can glean from this update.


The new look is the most striking change. All MobileMe web apps now share one toolbar with fewer icons. Starting from the right and working to the left, account information and logout buttons are in the same spot. The search bar has been moved to the far left on the new toolbar (below, top). Next, the strip of “action” buttons — Delete, Reply, Reply All, Forward, Refresh and Compose — have been replaced with Delete, Archive, Move to a Folder, Reply and Compose.

Finally, the series of app icons from the old toolbar (above, bottom) has been replaced by a single could icon (above, top). Clicking it brings up an application switcher (below), reminiscent of hitting Command-Tab in OS X. You’ll notice that the Mail, Calendar, Gallery, iDisk and Find my iPhone icons are the very same ones used by iOS devices.

Here are the other toolbars:

Contacts. The center icons are changed to New, Edit and Delete. The rest are the same.

Calendar. Navigation icons (Today, previous, Day, Week, Month and next) are in in the center. The rest are the same.

Gallery. Now Upload, Settings, Delete and Rotate are in the center. The rest are the same.

Find my iPhone. This one’s a bit different. There’s only the cloud icon, an option to refresh your device’s location and the login.

The updated Mail also offers three viewing options. Widescreen is a three-column view that puts mailboxes on the left, message information (subject, author and initial blurb) in the middle and the message body on the right. Classic view uses two columns with mailboxes on the left and the right-hand column split horizontally with message previews on top and the body below.

The compact view, which I’m using, is like widescreen minus the mailboxes (below, top). This layout resembles mail for iPad when the iPad is in landscape orientation (below, bottom).

The new preferences window has five options: General, Addresses, Composing, Rules and Vacation. Rules is the new feature here, and as this rounds out the UI changes, let’s see what that’s about.


At long last, users can apply rules to messages sent and received with the Mail web app. Unfortunately it’s limited in practice. Before we get into that, here are a few things to keep in mind.

First, rules are applied across devices. That means you can set up a rule in your browser and it will be applied to messages sent and received with your iPod touch, iPhone, iPad and Mac running Mail for the desktop. For me this is huge. Recently we put out a call for new bloggers at TUAW. I set up a rule to move applications to a target folder on my Mac, which worked well.

However, it didn’t apply to my iPhone and my inbox was cluttered with an avalanche of applications. And that’s just one reason I’m excited about cross-platform compatibility.

Also note that it can take a while for rules to “kick in.” I found my test rule started working in under 10 minutes. Also, you can re-order rules with a drag-and-drop.

What kind of rules can you create? Nothing too fancy, I’m afraid. The available actions are:

  • Move message to a folder
  • Move message to the trash
  • Forward message to an address

You can tell Mail to act on messages that

  • Are to a certain address
  • Are from a certain address
  • CC a certain address
  • have a specific string in the subject

That’s all I’d use, but  it won’t be enough for some users. Below are some screenshots of the rules setup screens.


One-click arching will move messages out of your inbox and into the archives folder for storage. Remember that your account comes with 20GB of storage, which you can allocate as you wish between iDisk and Mail. To make adjustments, log into MobileMe and select Account. Next, click Storage Settings. From there you can allocate your storage space. Click Save when you’re through.

I don’t use my email client as a file cabinet, but that’s another post entirely.

External email addresses

This feature was not a part of the beta. Users with multiple accounts can receive messages sent to those accounts with MobileMe. Additionally, if  you reply to a message sent to an external account from the Mail web app (and only the web app), you can have it appear to have come from that other account’s address. To set things up, simply forward the external address to your MobileMe address.

It’s interesting that MobileMe web mail and iOS are sharing so many visual cues. The Mail, Calendar, Gallery, iDisk and Find my iPhone icons in the new switcher are exactly the same as the corresponding iOS apps. Likewise, the compact view is nearly identical to mail on the iPad.

The similarities aren’t limited to software, either. Consider the new Mac mini. Its top looks awfully similar to the back of the iPad. The iMac’s display, with its glossy black bezel, resembles the iPad’s screen.

Of course, this isn’t the first time Apple’s design elements have spread across the line. The original iMac begat the G3 iBook. Then Mac OS 10.0 was release with shiny, aqua buttons. The original iPod ushered in the “white period,” and iBooks and iMacs followed suit.

That’s because Apple’s product line is practically a product in and of itself.  For now, iOS and the iDevices are receiving much creative time and attention. It’s clear that Apple believes that’s where the future of computing lies (a segment of computing anyway), so it’s logical that those visual cues would spread.

In the end, does this update mean you should become a MobileMe customer? No. If you weren’t convinced a week ago, this update won’t do it. Many of the MobileMe services can be had elsewhere. Others, like the stellar new Find My iPhone app, cannot. iDisk is still too slow, but the typically seamless synchronization of data across devices alone is worth it for some.

Current customers will love this update. Those waiting for more will continue to do so.