Here’s another one of the more useful posts I’ll be doing. Partly so that I can remind myself the steps needed to perform this somewhat convoluted approach to getting the best “setup” for iPhone and desktop mail use.

Why GMail Rocks

The best thing about GMail is the free IMAP support it has. For the uninitiated, make sure you read the advantages of IMAP over POP3 (referred to as POP from now on) in their respective wiki pages.

Of course GMail, just like any other competent email service, supports POP as well as the ability to retrieve mail from external accounts (via POP) as well. Not sure if it’s the same for other services, but this feature is free as well.

Couple that with IMAP accessibility, and lets not forget the gigabytes of space – and you basically have a powerful tool of accessing practically all your email in one place.

Refining it Further

Given the tools at your disposal, let me describe how I’ve setup my “mail workflow” – hopefully you can also find it useful in your situation.

What Exactly Do You Need?

This is the question everyone must answer whenever they plan to streamline their workflow. In my case, I need these conditions to be met:

1. Ability to access external accounts from one account.

I currently have about 6 active mail accounts; such as a work email, a personal email, “webmaster” emails from different sites I manage, etc.

As I’ve stated eariler on, GMail has the ability to access these (via POP).

2. Ability to “Send As” different addresses/identites.

Normally, not only would you want to consolidate email from external accounts – but also send from them… even if you’re ultimately just using one account (In this case, it’s GMail).

And personally, I hate it when other people change emails or cell numbers as often as they change clothes. As such, I try to make it a point that once I give someone my email address, it’s the only address they would need to remember… forever. And most people know my Yahoo address from the past. So even if I’m sending via GMail now, I don’t bother telling people about my GMail address since I still send out mail as nargalzius at yahoo dot com – even if it’s through GMail

Naturally, GMail also allows this functionality

3. Offline reading

It’s well and good that GMail can do all this awesome stuff, but I don’t like logging in the web interface since it’s slow, and more importantly, if your connection dies, so does your email session.

In order to access your email on a desktop (or phone) client, you’ll need either POP or IMAP support. And of course, GMail has both.

4. Synchronized message data on all devices/machines

The trouble with POP is that it’s only good for a single machine interacting with your mail server. By nature, POP doesn’t lend well to multiple machines that need to be in sync. IMAP on the other hand treats mail access exactly like a synchronization process – which is perfect for a multi-client setup.

In my case, I have the desktop, laptop and the iPhone all accessing my GMail account via IMAP. Any action I do on one computer is immediately reflected on the server – and naturally any changes on that server is immediately reflected on any of the other machines accessing it.

IMAP with Apple Mail

Now we know what we want (at least I do), so let’s start setting this shit up.

First order of business is to setup conditions #1 and #2. GMail’s Settings > Accounts section will let you setup POP access to all your external accounts, as well as allowing you to send email as those accounts from GMail.

It’s worth mentioning at this point that condition #2 works like a peach on GMail’s web interface; it isn’t as straightforward on Apple Mail – which is what prompted me to post this blog entry in the first place.

Next you get Google’s IMAP settings, which can be found somewhere in GMail (or the web if you know how to look), once you have that information, you’re ready to setup Apple Mail.

Just follow the IMAP setup instructions Google provided for the most part. But what I would like to mention at this point is that there’s a sort of undocumented “quirk” Mail.app has which will allow you to accomplish #2 with one account. Normally, you’d have to make multiple accounts… I’ll get into that later, for now, consider the picture below…

Notice I put multiple email addresses in the “Email Address” field. It should really be called “Email Address(es).” Anyways, populating that field with multiple email addresses (separated by commas) will give you this option when composing mail even if you only have one account active/enabled.

IMPORTANT NOTES

1. Make sure you add and verify your alternate sender addresses via GMails preferences (through the web interface of course). Even if you have multiple email accounts listed in your mail client (like in the photo(s) above), if they’re not registered in your GMail account, it wont matter what account you select as a sender; GMail will always send your mail as your default user@gmail.com
2. GMail has an unorthodox way of interpreting mail client actions via IMAP. What I mean to say is that if, for example, you select a message from the inbox and press delete; by default, it’s not going to delete that message – it’ll simply archive it. Likewise, moving messages from folder to folder will apply/remove “labels” on them according to the folder, so you’re not really “moving” anything.

More information can be found here.

Now for the iPhone

Now that you’ve setup your desktop(s) with an efficient way of handling all your emails from a single mail account – now it’s time to see what more you can do for the iPhone.

Bug, or by design?

Normally, if you simply sync your Mail settings on the iPhone, you’ll be good to go. But in the case of a GMail IMAP account, there’s one little thing that you’ll lose by just syncing that single account; that is condition #2.

Consider these two screenshots from the iPhone:

Both are IMAP connections but for some reason when the iPhone detects a GMail account it uses the preference layout on the left. Other generic IMAP accounts use the preference layout on the right.

The reason why the left sucks is that the “Address” field is also used for the login credentials – so it allows only one entry: your username/account (user@gmail.com).

The picture on the right on the other hand, has those credentials separate – which means that on generic IMAP accounts, you can use the OSX trick of putting multiple email addresses to accomplish condition #2.

That’s the reason why in the screenshot in the beginning of this post shows another IMAP account called “OTHERS” – you must’ve wondered “why would he have another active account if he accesses all his mail via GMail (the “Mail” account)? The answer is “it’s a workaround for the iPhone.”

Here are the settings I used on that account:

I used my own domain’s IMAP server for thisjust so it wouldn’t throw an error during setup (you have to have it access a working server). Otherwise it’s pretty similar to the GMail setup other than the fact that I did not populate the “Full Name” field. The reason for which is that I wanted to reduce clutter. I have webmaster accounts as well as personal accounts on there (including my primary Yahoo address¹ ). When sending as “webmaster” I don’t want my name displayed, and I thought in the iPhone’s case it would be just better to have it register only as an email address. It certainly beats having to setup another account just so I can use different “Full Names”

So now when I compose a mail in the iPhone, I’d have this option available:

Which wasn’t possible if you only had the GMail account on the device. I’d be sacrificing the “Full Name” on the iPhone, but I think it’s a small price to pay for the functionality I want.

If you’re getting confused about the whole “Full Name” thing, consider the screenshot earlier in the post The listing, when unblurred (but still paraphrased), is as such:

“Full Name” user@email1.com “Full Name” user@email2.com “Full Name” user@email3.com webmaster@email4.com webmaster@email5.com user@email1.com user@email2.com user@email3.com

Those three are ALL from the GMail account (who’s account username we’ll call user@gmail.com), which are selectable in the desktop but not in the iPhone.²

Unfortunately, while Apple Mail (desktop) supports multiple sender addresses, it doesn’t allow multiple sender full names to be set. Which is also why I just had to make the OTHERS account (for the webmaster addresses to be selectable without displaying my name)

The last 5 without the “Full Name” like I said, is from the OTHERS account. It’s basically a repetition of the addresses from the GMail account that can’t be chosen on the phone, plus the two webmaster addresses.

It’s a hack at best, but it works well… for now. Hopefully Apple updates Mail on both desktop and phone to handle these nuances better, but I’m not holding my breath.