Welcome to another instalment of Tips and Tricks, the series which aims to teach you something useful about one of your Apple products. This time, we’ll be focusing on Mail 5, the new version that ships with OS X Lion. There a few new tips that apply specifically to Mail 5, and also some existing tricks that should come in handy no matter which version you’re using.

Show your own messages in Conversation View

The new Conversation View (View > Organize by Conversation) in Mail 5 is great for keeping up with, well, a conversation. However, by default, it doesn’t show messages you’ve sent in reply during the conversation, which makes it harder to follow exactly what is being said and why.

To show your own messages in the thread along with those you receive from others, open Mail’s preferences, either under the Mail menu in the menu bar, or by pressing Command-comma. Then go to the Viewing tab, and under the ‘View conversations’ header, check the Include related messages option. Your sent messages will now show up in Conversation view.

Use Rules to color emails from certain people

If you’d like to highlight emails which came from someone important, like your boss, perhaps, Mail has a perfect way to do so. Using Rules, you can set the background color of an email in the list.

To do this, open up Mail’s preferences again, and this time open the Rules tab. Click the Add Rule button on the right, and a sheet will slide down with some options. Set the condition to From is [the person's email address]. Then underneath, set the action to Set color of background to [the color you want to use]. Click OK, and your rule will be added. From now on, whenever an email arrives from the address you specified, the message will be colored.

Show an unread counter in the Menu Bar

This tip will be useful to those of you who keep the Dock hidden, or have turned off the Dock unread count for Mail. This does involve downloading an extra piece of software, since Mail doesn’t support a menu bar item natively. The software is called Mail Unread Menu, and can be downloaded from MacUpdate. Once downloaded, all you have to do is run it, and you’ll have an unread count in the menu bar. There are also quite a few customization options available, such as the ability to choose the icon displayed in the menu bar for Mail, by clicking the menu item and choosing Preferences.

Change the names of Mail’s flags

In Mail 5, you can assign a colored flag to each message. There are seven colors to choose from, and they can be used for organising messages, since Mail automatically creates Smart Mailboxes for each flag you use. By default, the flags are named after the color of the flag, which isn’t very useful. There is a way, however, to change the names of the flags.

To change a flag’s name, first select a message and add the flag to it. Without adding the flag to at least one message, you can’t change its name. Once you have done so with all the flags you want to rename, you’ll see a new Flagged section in the Reminders area of the sidebar.

To rename a flag once it shows up there, right click it and choose Rename Mailbox from the menu. Then type the new name for your flag and press Enter.

Once you’ve pressed Enter, the flag’s name will change not only in the sidebar, but also in the drop down list of flags in the tool bar. This makes it much easier to remember what each of the colors means.

Flags also remember their names even if there are no messages with that flag applied to them.

Got any other tips and tricks regarding Apple’s default Mail app to share? Let us know in the comments.

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A full-screen world

While it may seem a largely cosmetic feature, in Lion, full-screen apps are assigned their own space and get pinned to the top of the screen when you access Mission Control. You can access Mission Control to see all your spaces by swiping up with three fingers. You can also swipe from space to space by swiping to the left or right with three or four fingers. Depending on how you’ve assigned your spaces in Mission Control, it may be quicker to access other apps than cmd-tabbing. One downside, though, is that multiple apps running in full screen can’t occupy the same space. The biggest downside to full screen is losing the ability to drag a file from the Finder to a mail message as an attachment. Naturally, if I kick it out of full screen I can drag attachments in just fine, so it isn’t a huge problem.

Conversations

If you’ve grown to like Gmail or Outlook’s message-threading features, you’ll also like how it works in Mail. If there’s a conversation, you’ll see the latest mail message in your Inbox and a counter in the lower-right corner of the preview telling you how many messages are in this conversation.

Each conversation looks like the above screenshot. While you can’t make the page graphic (message boxes with a raised, shadowed appearance) go away — setting “show classic view” in Preferences only changes how the Inbox list looks, not the conversation messages — I quite like the look.

Better searches

Apple advertises searches as being better: Simply type in anything you can remember and you should stand a better chance of finding what you’re looking for. Using a slew of search phrases I had great results. The only time it got stymied is when I searched “word attachment.” It can search for messages that have attachments, just not apparently the app attached to it. I couldn’t find an easy way to search all of my mailboxes at once; the best I could do is all of the Inboxes, which doesn’t do me any good if the mail message is my All Mail Gmail folder. For that, I found creating a Smart Mailbox was the best way to search everything thoroughly.

Cosmetic touch-ups

There are a few cosmetic items that are welcome additions. One is the ability to hide frequently quoted text, so you don’t get long email messages that also contain the previous 10 emails in the chain. You can also see the first two lines of the email in the message list, too. There’s a new Favorites bar that lets you pin frequently used folders to the top of the screen and displays the unread-messages count. Heavy folders and rules users should appreciate this.

Final thoughts

Mail in OS X Lion gets a much-needed upgrade. Mail was one of the Lion changes I was looking forward to, and it hasn’t disappointed me. I haven’t run into any of the problems I’ve encountered with previous versions (endlessly updating Inboxes, messages that refuse to be marked as read, messages that refuse to be sent, SMTP servers that refuse to be remembered). If, like me, you’re a heavy user of OS X Mail, I think you’ll like this new version.

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1. Microsoft Office 2004

Let’s face it, Microsoft Office isn’t cheap, and Office 2008 wasn’t that great. Some features in 2004 weren’t in 2008 (though many were reintroduced in 2011), and when 2008 included the new .docx format, 2004 users didn’t want to move to a new format that could cause problems. Because of these issues, it’s not unusual to find users two versions behind. Alternatives: Office 2011, iWork, Google Docs.

2. Appleworks

Appleworks, why can’t we quit you? I’ve been a fan of Appleworks since the Apple II days. You worked equally well on Mac and PC, and included a database that’s easier to use and understand that those used by either Filemaker or Access. In fact, Apple was still selling Appleworks until 2007. Fortunately, iWork will open most files in Appleworks format and Apple has a full transition guide about moving Appleworks files over to iWork. Database users will either need to export the file to spreadsheet format or move up to Filemaker. Alternatives: iWork, Filemaker, Bento.

3. Freehand

Die-hard Freehand users refuse to use Illustrator. Freehand MX was the last version released before the purchase and discontinuation of the product by Adobe. Freehand holdouts might balk at the cost of Illustrator, or at having to relearn using new software, but it’s time to move on, or Lion won’t be able to open your files. Alternatives: Illustrator (this guide will help).

4. Eudora

Eudora was an outstanding cross-platform email program and a longtime Mac standard. It easily imported into Apple Mail, Thunderbird, or Microsoft’s Entourage, but some of us, myself included, were lazy and didn’t import old emails. Instead, if I needed an ancient email, I just opened Eudora. Now’s the time to import those emails before you run into problems with Lion. And if Eudora is still your primary email program, it’s definitely time to move onto something else. Alternatives: Penelope/Eudora Open Source, Apple Mail, Thunderbird, Outlook.

5. Quicken 2007

Although Intel Macs have been out since 2006, Quicken still hasn’t updated the program. And Quicken 2007 is still being sold, because Intuit’s new product, Quicken Essentials, is a scaled-down version of its 2007 predecessor. Essentials lacks features such as bill pay and sophisticated stock tracking. Intuit generally keeps their Mac products somewhat behind the PC versions. Intuit’s suggestions for what to do with the end of Rosetta are laughable. Fortunately, a wide variety of alternatives exist for these users, but be sure to research these carefully, and import your data into a new program before you make the move to Lion. Alternatives: iBank, Moneydance.

What still-in-use programs will you have to say goodbye to when you make the leap to Lion?

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Distribution in the Cloud

Most cloud-based distribution solutions will create a shared, semi-public list for a group to use. Google, Yahoo and MSN each has its own “Groups” offering that provide a single email address solution. Send an email to that one email address (e.g. groupname@googlegroups.com), and all registered members of the group will eventually get the message.  ”Eventually” being the key word, since members may have changed their settings to receive one daily or weekly digest, instead of just each message as it arrives.  Plus these groups are an opt-in solution, and each member can opt out at any time, so there’s no way of making sure recipients get email when you want them to.

There Are Two Apps for That

There are two pretty good apps that help close the feature gap on managing distribution lists in iOS Mail: MerckTech‘s iEDL and Javid Alimohideen‘s Mail2Group.  The simpler of the two is iEDL ($1.99), which allows you to create lists using information from your address book or by manually enter email addresses. When you want to send a message to the list, select the group from within iEDL and it’ll launch directly into the iOS Mail app. Mail2Group ($1.99) has the same features and more. With Mail2Group, you can also copy groups, manually arrange the order of addresses within a group, and send up to six photos. The problem with both apps is that they don’t work when using the iOS SDK mail interface from within third-party apps.

A DIY Distribution List

The cheapest and most direct way to create a distribution list in iOS it to add a new contact and paste several comma delimited email addresses into just a single email field for the contact.  Sounds easy enough, but it does involve a lot of typing, making it much easier to create and maintain on a Mac, and then sync to your iOS device.  The process is the same on both platforms, however:

1. Create a new e-mail and manually add all recipients in the To: field. This is easier than typing in the addresses in full, since they should already be in your address book and will auto-complete.
2. Select all of the e-mail addresses and copy them into a plain text editor.
3. Delete all of the “Full Names” and <brackets>, leaving just the simple email@domain.com addresses, separated by commas (no spaces).
4. Copy the entire list as a single line of text.
5. Create a new contact and paste the entire list into one e-mail address entry for this new contact.
6. Save the new contact. That contact is now effectively a distribution list.

If you performed the above steps on your Mac, be sure to sync using MobileMe (if you’re a subscriber), Google or iTunes to get the new contact on each of your iOS devices.  Now your distribution list is accessible to Mail app as well as any third-party app that has Mail access built-in. You may find that some third-party apps require the use of semi-colons or spaces instead of commas. To get around this, simply create a separate one line e-mail in your distribution list contact for each format. For example, you could comma separate the “Home” address, semi-colon the “Work” address, and use spaces for “Mobile.”

Any other tips for making the most out of distribution lists on the iPhone?

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Apple has oodles of cash, and the love of millions of adoring fans. In general, the company also have a very good reputation for quality of design and build, and usability, but there are a few places where that sterling reputation isn’t backed up by experience. These are the things I’d most like Apple to fix:

Lame Headphones

I now own so many pairs of white earbuds I could probably outfit an entire NBA team with the things. Of course, NBA players would never use them, and neither would I. The in-ear headphones Apple released in 2008 were a bit better, but just a bit, and after less than a year, mine failed. Instead of opting for another pair, I went with a third-party solution.

According to a new patent found by Patently Apple, we might soon see better headphones from Apple, with much-improved noise cancellation for making calls. The materials Apple uses in its headset construction do make them pretty much tangle-proof. But if Apple doesn’t pay more attention to actually increasing sound quality, I’ll still leave the things in the box.

Custom Sounds for Text Message and Email

This is just cruel. Apple provides all iPhone users with the option to select whatever ringtone they want, though you have to convert your audio file of choice first. It’s still not hard to do, though.

But what if you want incoming texts or emails to make a noise that isn’t in the stock set? It sure would come in handy when you’re at tech trade shows or special product announcements to avoid confusion. In order to do that, you have to jailbreak your device. All I want is for my phone to make an R2D2 noise when I get a new text. Is that modest level of customization really too much to ask from Apple’s wunderphone?

A Better Mail Program

Mail.app is okay, but it’s just okay. The problem is, there’s scant competition out there, beyond Postbox, which is probably a little too feature-heavy for most users, and Outlook, which is a Microsoft product, so it feels like a betrayal. Plus Outlook is apparently quite buggy at the moment.

Apple’s built-in mail client has remained relatively unchanged for quite  a while. Most frustrating of all, none of the changes it did receive with the Snow Leopard upgrade fixed its most annoying problem: a chronic failure to actually make the “New Mail” sound when new mail arrives. I’ve searched far and wide for fixes, and there doesn’t seem to be a permanent one. At least my iPhone can consistently notify me when I get new mail, even if I can’t change the sound.

Multi-Format Video Support in iOS

iOS devices support at least a few different audio formats, including .MP3, the most widely available variety. But video support is limited only to specially formatted .M4V, .MP4 and .MOV formats. Just give us some DivX love, Apple.

Obviously, Apple wants to make piracy more difficult for users by limiting the video formats its devices can play, but people who really want to use pirated media will be the ones who find the converters that let them do so anyway. All that’s achieved by preventing average users from loading their own videos is device owner frustration.

Yes, apps like VLC have made this less of an issue, but broader native codec support would make things far easier for everyone.

Just Fix It

Like I said, generally speaking, I love what Apple’s doing. Life without my iPhone 4 and iPad and at least one Mac computer is pretty hard to imagine these days, which is why I become really annoyed when I think about these relatively minor things that would be so easy to fix for a company with $50 billion in cash on hand.

There have to be more things like this that I’m missing. If you can think of any, please share in the comments, or on Twitter followed by the hashtag #pleasefixthisapple. We’ll be watching, and your suggestions might make their way into future posts.

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The just-released Postbox 2.0 introduces a handful of new features that include Quick Moves, a Focus Pane, Quick Replies and better Conversation Views.

The threaded Conversation View is pretty well done with quick reply buttons readily available to respond to any particular email within the chain. I also really like the Inspector Pane that gives you some shortcuts, including all the links contained within the email thread.

The Focus Pane is all about organization. Quickly navigate to emails that match a date or topic, or are unread. If you want to deal with an email later, drag it to the “Later” topic and come back to it or click on “Today” to see emails only from today. The idea is that if organize your mail better, you’ll save time and be free of distractions.

Speaking of distractions, you can post directly to Twitter, Facebook or FriendFeed from the menu bar also.

Pros:

Conversation View is very well done, with quick navigation, and the Inspector Pane could be very useful for link-happy users. Organizing mail into topics is accomplished quickly by dragging and dropping. The Focus Pane drills down to what’s really important. Keyboard shortcuts are a time saver for those who like to keep it old school.

Cons:

It’s $40, and the free Apple Mail works well enough for most. Organizing mail into topics requires commitment, and not all users care that much. There’s also no Exchange support. This is disappointing, considering Apple Mail has it built-in and business users can be notoriously organized when it comes to email.

Summary:

Postbox 2.0 supports POP and IMAP protocols, but has no Exchange support. There’s a 30-day trial, and it’s $40 if you want to keep it after that. If Apple’s Mail isn’t quite delivering and you need more organization, Postbox is probably the solution for you.

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In this TechUniversity Mail 101 screencast (subscription required), we’ll walk you through…

• Setting up a POP and IMAP email account in Mail
• The Mail interface
• Sending an email
• Organizing your inbox

Below is a sample of the video. The full screencast clocks in at just under 15 minutes.

In this TechUniversity HTML Signatures in Mail screencast (subscription required), we’ll take a look at how to create a custom HTML signature for use in Mail.app.

View the full HTML Signatures in Mail screencast on TechUniversity (subscription required)

Screencast Sample

Maybe ‘broken’ is too harsh a word, but it definitely hasn’t made for a pleasant web-based email user experience. As someone who also maintains a Gmail account for back-up purposes, there really is no comparing the two experiences. One is pleasant and intuitive, and the other has been, till now, awkward and uncomfortable.

The new MobileMe Mail Beta makes a number of changes that, though small, completely change the look and feel of using the web app. Here’s a rundown of what’s new and different.

New Views

MobileMe Mail’s physical layout can now be switched among three different views, including Widescreen, Compact and Classic. Each offers unique advantages and suits different monitor setups or screen arrangements. For example, I generally keep my mail open on a secondary monitor that’s oriented in portrait mode. Either Compact or Classic represents a better look for this type of setup, because you can see more information in a narrower space. Widescreen is great for when I have my second display flipped in landscape mode, since it resembles Mail on the iPad.

New Interface

MobileMe Mail looks a lot different in the new beta. In fact, it no longer shares the design elements of its other MobileMe web apps, like the iPhone-inspired icon bar at the top and the black top bar. Instead the theme is blue and white, with a single button that sends you back out to your Contacts web app, which still has the old navigation bar.

The search bar is located above your inbox instead of on the far right side, which is a much more intuitive place for it to be, and in keeping with how message search works on both the iPhone and iPad platform. Things like that and the icon choices for your common mail actions (Delete, Archive, Move, etc.) seem to indicate that Apple is trying to tie the MobileMe web-based product to the iPhone platform.

The changes really do bring a sense of uniformity across Apple’s platforms. All we need now is a new version of desktop Mail on the Mac that also borrows design cues from the iPhone and we’ll have true product continuity.

New Message Editor

Hitting the compose button now results in a completely different experience compared to that of the original Mail web app. The interface is clean and sparse, but still presents you with a much larger selection of composition options via the new formatting toolbar.

The 14 font options, color picker, list formatting button, link insertion and tab control mean that using webmail is now a lot more like using Mail via a desktop client. You can now personalize your email completely, and drafts are autosaved with considerable frequency to prevent losing messages, something which happened often in my previous experience with MobileMe on the web.

Persistent Rules

You can now create rules in MobileMe web mail that will apply across your inboxes, on all devices associated with your MobileMe account. What makes this so great is that doing so using the web-based interface is far simpler than creating rules using desktop Mail.app. Just click the settings icon, then in the ‘Rules’ tab add and edit any rule you want. On the desktop it takes a bit more hunting around to find these features.

Little Things

The little things really make MobileMe better. It feels snappier and more responsive, and seems to function much better in terms of composing and reading email, both areas which always seemed buggy in the old version. And little touches like the one-click archiving button, inbox refresh button and quick folder addition intuitively located next to the “Folder” menu item instead of tucked away at the bottom of the interface all combine to make this beta a winner.

In fact, I much prefer the interface on my iPhone, and that of the iPad Mail application is better still. Which is why it’s great to see Apple release a new beta version of MobileMe’s web mail app that borrows heavily from its cousin on the iPad.

To get started using the beta, all you have to do is be an existing MobileMe subscriber (or sign up for a new account, I suppose, if you’re that interested, although buzz is building that it might become free soon), log in to your account and click on the “Request an invitation” link that appears in the bottom lefthand corner of the current interface. Apple will then send you an email invitation when you’re added to the beta pool.

Here’s what you’ll get for your trouble:

• New widescreen and compact views allow you to alternate between an iPad-like display mode that shows you more of your message, while also giving you access to your folders. Compact view gets rid of the folder navigation pane, and you can still switch back to classic view if you preferred the way things were.
• A new formatting toolbar means your messages won’t have to look so drab going out, and you can format long URLs to keep outgoing mail nice and tidy, and less likely to trip junk mail sensors.
• Set rules from the web view to filter out unimportant emails and cut down on inbox clutter. Whereas before you had to set these up in desktop mail, you can now create them on the web and have them automatically apply on both your desktop client and on your iPhone, iPod touch and iPad. Not to mention the PC, if you happen to be using MobileMe with Outlook.
• Increased performance like faster loading and continuous scroll combine with increased security to give you a better overall web-based emailing experience. Plus, clicking the “Archive” button provides a handy, one-step way to file messages away without losing them for good.

An interesting side note would be MobileMe beta users: Apple recommends Safari 4, Firefox 3.6 and Internet Explorer 8 as the browsers of choice for use with the beta. Wonder why they left Google Chrome out of the party? Pretending your competition doesn’t exist won’t make them go away, Cupertino.

Folders

Many have desired a way to better organize apps on their device. When Apple introduced the App Store, it also gave us multiple home screens. Organization got a bit easier with iTunes 9 which allowed for organizing home screens directly from within iTunes. Taking the idea even further, device-wide Spotlight made it easy for users to find apps no matter which home screen they were on, or even if they couldn’t be displayed because of display limitations. When iPhone 4.0 launches this summer though, users can also organize their apps into folders.

As you’d expect from Apple, the process is quite simple. Just tap and hold an app until it starts to wiggle, just like you were going to move its location. Then drop the app on top of another app’s icon and a folder will be created. The device will use the genre of app (Business, Games, etc.) to define the folder name, but this is, of course, changeable.

Allowing organization within folders will mean that users can now keep many more applications on their devices than before. In fact, Apple says that you could, in theory, store over 2,100 apps on the phone now.

Mail

If there’s one thing that constantly seeing “Sent from my iPhone” has taught me, it’s that iPhone and iPod touch (and now iPad) users all love checking their email. The next version of the iPhone OS will bring some improvements to this much-loved app. The one I’m most excited about is support for multiple Exchange accounts (which is great since I have two at work).

Like Mail.app on the Mac, this new version will also support a unified Inbox, allowing you to see messages from all of your accounts in one view. It will also support threaded messages, making correspondence easier if you’re an email junkie. It’s also easy to switch between inboxes with “fast inbox switching.”

Finally, the new version will also allow you to open attachments that are associated with third-party applications.

iBooks

The success of iBooks on the iPad is unquestionable. With the iPad not even a week old and only available in the United States, Apple has announced that over 600,000 iBooks have been downloaded.

Just like it’s iPad cousin, the iPod touch and iPhone version if iBooks will allow you to browse and buy books directly from the iBookstore. If you’ve already been buying content for your iPad, all of that will sync up through iTunes to iBooks on your iPhone. In addition, your bookmarks and information on the last page you were on will be synced as well.

What do you think of these announcements? Some of these features may only be available to iPhone 3GS or third-generation iPod touch users. Is it time for you to upgrade? Share your thoughts in the comments.

Apple’s original implementation of “smart” file management isn’t just limited to the Finder, and in fact, you’ve probably seen it more often in other applications like Address Book and Mail.

Here are some ideas of how you can harness the power of these two applications using the same idea as Smart Folders.

Smart Groups

Address Book provides support for smart groups which allow for dynamic content, just like a smart folder. As new content is added that meet your guidelines, the group will automatically update.

Creating a Smart Group is as simple as going to File and selecting “New Smart Group…” or by clicking the plus icon (+) in the lower left corner of the Address Book window. Then give your group a name and set of criteria. As you add your second criterion, you’ll have the choice for your group to consist of any of your rules or all of your rules.

Here’s some ideas for useful smart groups.

Upcoming Birthdays

Interested in who might have a birthday this month? Set the birthday criterion to include entries that occur within the next month. (This will include all birthdays within a month of the current date or when you click to view the group.)

Missing Email Addresses

To see a list of people who you do not have an email address for, set the email criterion to include entries that are not set.

My Coworkers

Most companies offer their employees an email address that uses the corporate domain. If you created a smart group for “email” that contains “yourdomain.com” then you will have a group that is always updated with all of your coworkers. An extra bonus, these Smart Groups also show up and autocomplete in Mail.

Or Anything You Want

Since the Address Book allows for a “notes” section on each card, you can use this region to “tag” cards and then use a smart group to show results based on that information. (You could also repurpose one of the other standard fields for this use.) For example, throwing the word “family” into the appropriate contacts’ card would allow for you to create a smart group that just showed your family members.

Currently, Smart Groups cannot be synced to iPods or iPhones. While they also cannot be synced through MobileMe to me.com or Windows computers, they can still sync through MobileMe to other Macs.

Smart Mailboxes

Mail has its own flavor of smart file management too with the implementation of smart mailboxes. To create one, use the Mailbox menu or the plus (+) icon in the lower left of the message viewer and select “New Smart Mailbox.”

Give your smart mailbox a name and choose the appropriate criteria for your mailbox. With the ability to create criteria based on recipient, subject, mailbox, date, message, attachment and more, you can create some pretty powerful mailboxes to help organize your workflow. Here’s a few suggestions.

Recently Viewed

Most people process tons of email on a daily basis and frequently people have multiple email addresses for different purposes. With all of these messages, is there an easy way to find that email you were looking at last night?

Sure! Create a new smart mailbox and select “date last viewed” and choose “is in the last” and specify a number of days.

Recently Sent

If I wanted to quickly find an email that I had sent recently, I could create a Smart Group that showed me messages in the mailbox “Sent” that were “date received” in the past 2 days. Also make sure you tick the “Include messages from Sent” checkbox.

Emails from My Family

Remember the family smart group we made in our Address Book earlier? We can create a smart mailbox to show us all the messages from those family members.

Select “Sender is Member of Group” and then choose the appropriate group from the drop down menu.

Similar to Smart Groups, Smart Mailboxes do not sync to iPods or iPhones nor to me.com or Windows computers through MobileMe. They will only sync via MobileMe to other Macs.

Do you use Smart Groups or Smart Mailboxes? Have any tips you’d like to share? Share them in the comments.

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Ooops. Seems I spoke too soon. TidBITS reports that some users who upgraded to Snow Leopard, Apple’s latest incarnation of its Mac OS X operating system, have been experiencing problems sending email using the native email client, Mail.app.

When trying to send mail, hapless users have been getting an error message that reads “Error 54: Connection Reset By Peer.”

Of course, I know what you’re thinking. “Error 54?” you’re saying, as you stroke your Tech Guy Beard of Truth, “Sounds like an issue with port rotation. I probably need to update my SMTP settings.”

A quick look at the newly added Article TS2998 over on Apple’s Support Knowledge Base confirms your Oracle-like insight. According to Apple:

In Mac OS X v10.6, Mail sends messages through a different port rotation for the “Default ports” setting. Your authentication settings for your Mail account (for outgoing messages) may need to be updated.

Just follow step-by-step instructions for updating the offending account’s SMTP server settings.

Several days ago, during Gmail’s recent hiccup, I had just upgraded my machines to Snow Leopard and found I couldn’t send mail from my Gmail account. At the time, I assumed it was caused by the server difficulties Google was having and, seeking a quick and easy fix, I removed the account from Mail and have been using Safari to check my Gmail ever since. It seems, perhaps, I was wrong to assume it was Google’s problem. Perhaps I was experiencing exactly the problem described above.

I don’t feel too foolish for failing to suspect my new big cat was the culprit; after all, everything else works perfectly. Following such a major upgrade, all my hardware and software work exactly as they did on the old feline. I’d like to extend the metaphor a little further — probably something about cats toying with their prey — but I’m gonna stop before it gets outta hand.

Have you experienced the same problem with Mail? Did the fix Apple recommend work for you? Is this a bug in Snow Leopard, or the result of Mail becoming a more secure email client? Share your thoughts with me in the comments, and I promise I won’t use the cat metaphor again.

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What You Will Need

• Your Mac
• Your iPhone (it needs to be jailbroken)
• PlistEdit Pro (or another application capable of editing plists)
• Coda (or another application for editing HTML)

Before We Begin

To use a custom CSS signature, we will be modifying a preference file on your iPhone. Simply using copy and paste within the new 3.0 OS will not maintain the HTML and formatting of our signature. Your iPhone should already be jailbroken and capable of mounting as an Apple File Protocol (AFP) share on your Mac. For instructions on this process, see here.

Step One

Once you have logged into your iPhone over AFP, browse to the following location:

/private/var/mobile/Library/Preferences

Copy the file com.apple.mobilemail.plist to your Mac. Go ahead and duplicate this file, appending “backup” to the end of the filename so you have a clean copy in case something goes wrong.

Step Two

Open your email signature that we created (see the original post here) in your HTML editor and copy the contents to the clipboard.

Step Three

Use PlistEdit Pro to open the file you copied earlier in Step One. Towards the bottom of the list, you will see an entry called “SignatureKey.” The value for this string will match your current iPhone signature.

Double-click this value to highlight the contents and delete what’s there. Now paste the HTML code for your email signature that we copied in Step Two. Save this file back to your desktop.

Step Four

Browse back to the Preferences folder on your iPhone. Copy our new edited plist file and replace the original on your iPhone.

Step Five

All done! Create a new email and you should see your HTML email signature at the bottom.

Limitations

Unfortunately, due to limitations in the iPhone 3.0 OS, Mail on the iPhone only supports one signature. There are third-party applications available on the App Store that address this issue, but I have not tested them with HTML email signatures. Hopefully in a future OS update, Apple will allow users to have unique signatures for multiple mail accounts.

This process and file location has remained the same since iPhone OS 1.1.4 and will likely remain the same, meaning as new OS updates come out, they should not break this functionality (unless Apple adds support for multiple signatures at some point). However, if an update does break your signature, the process outlined above should still work to put it back.

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As any person who frequently uses email will tell you, email signatures are very important as they usually provide more information than just a standard name and email address from the sender. You can spice up an email signature since Mail offers support for HTML signatures. If you are fairly comfortable with getting your feet wet with HTML & CSS, they are a snap to create. Read on for how you can make one!

A Note on iPhone Support

This how-to is written specifically for Apple’s Mail in OS X. Also, these signatures will display on an iPhone, but currently there is no method (aside from jailbreaking) to support these signatures on outgoing emails originating from an iPhone. Depending on the amount of content in your email signature, you may need to further tweak the CSS to get something that looks the way you want it to. For those who have already jailbroken their phone, look forward to an upcoming article on how to accomplish these signatures on your iPhone.

Let’s Get Started

Here is a quick example of what we will be creating.

For this how-to, you will need Mail, Safari and some type of HTML editor; my preference is Coda. Our email signature is simply an HTML page with some CSS styling. The code for mine is included below.

<style>
#sig a:link{color: #690;}
#sig a:visited{color: #690;}
#sig a:hover{color: #690;}
</style>
<div id="sig" style="-webkit-text-size-adjust:none;line-height: 14px; margin: 6px 0; padding: 8px; border-top: 1px #999 dotted; border-bottom: 1px #999 dotted; font-family: 'Lucida Grande', Verdana, Arial, Sans-Serif; font-size: 10px; color: #555;" >

<strong style="color: #690;">Chris Ryan</strong> Blogger, Designer, Thinker & Nerd
web: <a href="http://www.theappleblog.com" style="color: #690; text-decoration: none; border-bottom: 1px #999999 dotted;">theappleblog.com</a> email: <a href="mailto:chris@theappleblog.com" style="color: #690; text-decoration: none; border-bottom: 1px #999 dotted;">chris@theappleblog.com</a></div>

Copy this code (tweaked for your own purposes) into a new HTML document and save it as signature.html. Now open this file in Safari and inspect it to ensure that everything is correct as you would like it to appear in the bottom of your emails. Be sure and click the links to make sure they work correctly as well (and link to your content and not mine!).

If everything looks good, then go to File and pick “Save As” and save the file as a .webarchive. This is the same format that Mail uses to save your signature files.

Our next step is to go into Mail and create a new blank signature. This is found under the Mail menu and by clicking on Preferences. In the Signatures tab, you can click the plus icon to add a new signature. By default, Mail will pre-populate this signature with your name and email address. What has really happened is Mail has created a new .webarchive file with that signature content. We’re going to replace it with the file we created earlier.

Close the Signature window and quit Mail (changes should be saved automatically). Now go to your home folder and then open the Library folder. Inside you will find a Mail folder and inside of that, yet another folder called, you guessed it, Signatures (Home → Library → Mail → Signatures). Inside of here are the .webarchive files for your signatures. If the signature you created above was the very first one, there should only be one file in here. If you already have multiple existing signatures, you can double click these files and use Safari to inspect their contents.

Locate the file that matches the simple new email signature we just saw in Mail. With the icon selected, press return as if you were going to change the file name. When the file name highlights, copy this to the clipboard (Command + C) and press return again to switch out of file renaming mode.

Go back to the desktop where you saved the .webarchive of your signature file and rename it using the filename you copied to the clipboard. You should now have a file with a very cryptic filename (such as “AAD4FDB4-8AE3-49F2-8079-161E16525CC0.webarchive”).

Now, drag this file back into the Signatures folder and Finder will alert you that it wants to overwrite this existing file. Click “Replace” to accept and when the transfer is complete, your Signature should be ready to go.

Launch Mail and go back to your preferences to verify the new signature is showing up. If you have multiple email accounts setup within Mail, make sure you drag the signature to the appropriate email accounts.

Create a new message and viola! Your new signature is there (or if you do not have them turned on by default, they are accessible from the Signature menu in the upper right area of a new email message window).

One Last Word On Coding

One special piece to note about the example code above is the usage of -webkit-text-size-adjust: none; which overrides the iPhone’s default attempts to re-scale the signature. This was essential in making my signature look best on the iPhone. Again, with the amount of content you have in your signature, you may need to play around with the CSS to get something that displays the way you want when you view your sent or received messages on the iPhone.

Depending on your comfort level with CSS, you can tweak the signature a bit more and even add a small picture. Some HTML based email browsers, like Yahoo or Gmail, will not display this picture by default though. There are other solutions to this, such as using Data URLs to represent your picture and for more information on that, check out this how-to.

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I’ve flipped around between QuickOffice, Documents to Go, and Notes to handle this, but I was never satisfied. Notes and Documents to Go go require me to be on my Mac and sync to it. That’s overkill for a shopping list. I don’t mind the iPhone keyboard, but typing “2 cases of water” with another phone jammed in my ear is awkward; it’s much easier to just type it on my work computer. Plus, syncing often just feels like a bother, doesn’t it? Not to mention lengthy with the “let me me nip off to the pub while this backup runs” issue that’s back with 3.0.

What worked best was QuickOffice writing the file to an iDisk. But iDisk is all I would be using from MobileMe, and I just can’t get my mind around paying $99 a year for that convenience. Not to mention, handling simple text through the .doc format just seemed overkill. I could work off the cloud, but if I’m in a low signal area, I’m out of luck.

So, the solution I’ve found myself going with is using Drafts in the iPhone/Gmail web interface. I can create a draft, give it a title and merrily type away on the iPhone. When I save it, it syncs to my Gmail account where I can edit the draft on any computer that’s connected to the Internet. As long as I don’t put in a recipient, it wont get accidentally sent. I also don’t need to worry about initiating a sync; it all happens in the background.

How about you? What solutions to this problem have you found?

iPhone Mail Drafts

Gmail Drafts Screen

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