10 Ways to Soup Up Apple Mail
If you're "going postal" dealing with your email, our powerful customization tips will make everything copacetic again.

Microsoft Office for Mac 2011 arrives at the end of October, tempting us all with the powerful new Outlook 2011 email client (formerly called Entourage)--but the Home & Business Edition of the suite is $199. So why not take a second look at Mail, the free email client that Apple includes with every Mac? Mail is a capable application, but Apple likes to keep its software simple, so it lacks the advanced features of Outlook 2011 or even Entourage 2008. But with a few tips and some extra pieces of inexpensive software up your sleeve, you can beef up Apple Mail to be just as powerful as Microsoft’s email programs.
Difficulty Level: Easy
What You Need:
>> Mail (included with Mac OS X)
>> Various optional plug-ins and add-ons (prices vary, see below for details)
1. Better Rules

Mail Act-On ups the ante with Outbox rules.
Mail Act-On ($24.95, indev.ca) takes setting rules for your email to a whole new level. You can quickly create complex sets of conditional rules using and/or logic, manually apply groups of rules to any selected set of messages, and undo any rule that you mistakenly applied. It even lets you assign rules to outgoing messages so you don’t have to rely on searching your Sent Mail folder. Control your rules with keyboard shortcuts or through Mail Act-On’s floating window.

Control rules with key commands or this floating popup.
2. Fly Those Flags

Flagit makes it easy to add colors and custom tags to your messages.
To quickly add colorized, customized flags to your email messages, like Entourage’s similar Assign Category function does, you need Flagit ($15, tastyapps.com). By default, Mail only includes one kind of flagging, but Flagit gives you more options, easily accessed in the contextual menu when you right-click a message.
3. Tag, You're It

MailTags puts a whole new world of organization at your fingertips in the right margin of every email message.
Sorting mail into folders works, but you can’t put an individual message in more than one folder. Tagging is the solution. Mail doesn’t natively offer a tag feature, but MailTags ($29.95, indev.ca) lets you append tags, keywords, projects, priorities, and notes to all of your messages.

MailHub adds a new toolbar to Mail, which makes it easy to file, delete, or schedule individual messages or entire message threads.
If you want a reminder to take action on an email at a later date, MailTags lets you link your emails to events and tasks in iCal. MailTags also modifies Mail’s list view, smart mailboxes, and rules, so that you can customize all of those elements to recognize the extra tags that you’ve created. If you just need an easier way to file your messages and schedule reminders, check out the less expensive MailHub ($19, hungerfordroad.com).
4. Notify Yourself

Give yourself floating notifications whenever new email messages arrive.
Entourage and Outlook have a floating notification window that appears when you receive new email, giving you a preview of each message without making you leave the application you’re working in. You can add this same feature to Mail by installing Mail.appetizer (donations requested, bronsonbeta.com) or GrowlMail (free, growl.info). Both of these programs offer much more customizability than Microsoft’s notifications.
5. Look to the Dock

One glance at Mail's Dock icon tells you everything you need to know about the state of your inbox.
If a floating notification window isn’t enough for you, you’ll love DockStar ($15, ecamm.com), which supercharges both your Mail Dock icon and the menu bar at the top of your screen. You can add up to five customizable badges that display the count of unread messages, flagged messages, junk messages, new RSS articles, notes, and to-dos--for any accounts or any folders that you choose.
Next Page: Soup Up Apple Mail continued »
AMCarter3
March 14, 2012 at 3:56pm
I highly recommend Mailhub. I've used it for more than a year now and could not live without it. If you store emails in your own folders, Mailhub is THE tool to have. It not only stores incoming email easily and intuitively for you, but it also stores out-going email too! No other email client or add-on offers this capability. Despite Apple Mail's weaknesses, with Mailhub added on it is a superior choice over Outlook and any other email program.
emmettmclaulin
March 07, 2011 at 8:01pm
I think some of these apps are pretty cool. I have 2 exchange accounts and a mobile me account. Generally apple mail has been very good. But there is a lot of functionality you can't access without Outlook 2011 or Entourage. My beef is that many of these apps get wiped out when apple makes changes.
For example letterbox was one that I used to like that now resides in the disabled plugins folder...
My opinion is that Apple being so well known for it's thoughtful products (meaning well engineered.) should build a great deal more functionality into core native apps. Especially since they are really seeking to extend into business community.
You can build functionality and simplicity together.
Out of this batch I have tried mail tags. It is pretty solid. It just seems silly to spend 30 on an app plugin. You could purchase Outlook and all it's functionality for $30-50. BTW, I am not an outlook lover. It's just a financial comment.
Cheers
wheatenwade
January 03, 2011 at 10:26am
I would highly recommend Herald as a Snowy compatible replacement for Mail Appetizer. Erik, the developer, does a great job of keeping it up to date.
http://erikhinterbichler.com/software/herald/
pipower
November 13, 2010 at 7:05pm
I don't know why you're recommending Mail.Appetizer. It's not compatible with Snow Leopard.
29Mac
November 09, 2010 at 10:20am
You didn't mention the best of all Apple's built-ins:
While in Mail, click command-i to see what mail is on your ISP's server. Can delete inbox garbage directly without ever downloading it.
bradleydad
November 09, 2010 at 8:48am
Does anyone else attach photos to their mail?
If you use iPhoto you can't browse to your pictures very easily.
Previously, one could send photos directly from iPhoto, which was a good reason to use mail. But with the new version of iPhoto, you can only send dumb looking post cards which only allow 4 lines of text. (And are larger image files.)
Is there any workaround to Apple's stupidity except dragging them over? (So now you have either full size or very small pictures.) And, if you are using spaces, mail and iPhoto need to be on the same space.
rlscharf
January 03, 2011 at 2:57pm
bradleydad,
The latest update to iphoto 11 allows you to chose mail as the default for sending pictures, just like before. I changed my preferences to that and now am a happy camper again. Go to: iphoto>preferences>general>email photos using (choose your poison). Have a good one.
jvputten
November 08, 2010 at 5:51pm
So, $177 dollars in shareware fees later, this is going to fix all my problems.
Pass.
MrFuzion
November 08, 2010 at 5:16pm
I tried so many different times to use Apple Mail, and every time went back to Thunderbird. Mail consistently had issues connecting with mail servers, to the point that I spent more time deleting accounts and readding them than I did actually reading email. Once I went back to Thunderbird...no issues EVER. I'm actually disappointed, as I'd have loved to use a lot of Mail's integration features. Still, Thunderbird works really well with no problems (for me, at least).
skiziks
November 08, 2010 at 2:49pm
Good article about how to soup up Mail.
The decision has been made to migrate to Mail from Entourage.
I would like to see some exact instructions to follow to make a seamless transition to Mail from Entourage 2008.
Importing everything to Mail is not a familiar step for everyone. Some of us need some hand holding.
dbh97
November 07, 2010 at 7:32pm
Your link to TidBITS Auto correct should be
http://db.tidbits.com/article/10567
not
http://www.db.tidbits.com/article/10567
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