Look South

By Dave South

GmailMe — A mashup of Gmail and MobileMe

Managing email is a royal pain. Especially if you read email on more than one device. After buying iPhones last year, Mike and I worked up an excellent system of managing our email on the iPhone, computer and web.

At the time I had multiple email accounts — a system administration account, a business account under one domain, another business account under another domain. It was painful keeping track of which email came on what account and what account to use when I wrote an email.

The new system streamlined everything. All email filters into one system and one master email address. It turns out that nobody really cares what your email address is — once you establish a connection.

A year after our first article, our set up is a bit more refined. With the upgrade to iPhone and MobileMe, it’s time to upgrade our instructions and maybe explain why we do it this way to begin with.

Own your domain

It’s vital that you always own the domains you advertise. What does that mean?

Let’s say John Doe is at a networking meet-up and handing out business cards. John is very proud of his new website — http://www.example.com. But on his business cards, his email address is listed as rumplestiltskin@weirddomain.net.

It’s unprofessional. John went through the trouble of buying a domain and implementing a website. Can’t he take the time to get an email address using the same domain? It immediately says he’s an amateur on the Internet.

More importantly, by using his Internet service provider’s email account, he’s advertising an email address that can — and probably will — change. When his cable company offers him a better deal for Internet access, he’ll have to go through a painful switch, explaining to every one that his email address has to change because he’s switching providers.

1. Own the domain of all email accounts you advertise

Every one of them. On business cards, letterhead, everything. Don’t waste time handing control of your advertised email accounts to anyone.

That doesn’t mean you must have a real account behind every email address. That was the mistake I was making in the past. Instead, for every email address you create on your domain, have it forwarded to one master email account.

One account to rule them all

Your master email account must be robust, not attached to any ISP, and have powerful spam filters. Gmail is the best we’ve found so far. It’s free (or very cheap at $50 a year). They have the best spam filters of all time. And it can hold huge amount of information. Right now they provide 7 gigabytes of storage.

Gmail does not advertise in the outgoing email. You can use Yahoo or MSN, but they always attach a small ad on every outgoing message. This is unacceptable. Gmail can even pretend to be from one of your domains (with caveats, see below).

2. Set up all domain based email addresses to forward to Gmail account

We use GoDaddy for most of our domains. Other domain registrars offer similar services so these instructions should work with them, too.

For every domain I have with GoDaddy, they give me 100 forwarding email addresses. It’s super simple to use the GoDaddy interface to add a forwarding order such as “john.doe@example.com” should forward to “john.doe@gmail.com”.

Do this for every email address you own. Forward them all to that single account.

Gmail is a lousy IMAP server

IMAP is the key to managing email on both the Mac and an iPhone. It allows each device to directly manipulate email on the server. The strength of Gmail — the massive space so you don’t have to delete any messages — is terrible when using IMAP. The mail clients on the Mac and iPhone download a cache of each message. For a large Gmail archive, this can take hours and uses a lot of space on the iPhone.

Having a copy of the entire Gmail archive on the Mac is pointless. The only email that matters is the current email — new messages, working copy, letters to answer, pending processing. The rest should just be left on Gmail where it can be searched using Google’s fabulous search engine.

3. Set up Gmail to forward to MobileMe

It doesn’t have to be MobileMe. Any decent IMAP server will work. I use MobileMe because I like the “push” contacts and calendar. It has a nice web interface. The iDrive is great, too.

To set up Gmail to forward properly to MobileMe.

  • Open the Gmail account, click on “Settings”, then “Forwarding and POP/IMAP”
  • Under forwarding, click “Forwarding a copy of incoming mail to”
  • Add the MobileMe account (john.do@me.com)
  • Set the select option to “archive Gmail’s copy” so every message will be saved in Gmail after being sent to MobileMe.

Disable POP and IMAP because we just are not going to use them with Gmail.

Gmail is the best spam filter

Where Gmail beats everyone else is in spam filtering. I have never used a better spam filter. The best part of this mashup is that Gmail will filter all spam messages before forwarding them. So all spam will be caught by Gmail and not transmitted to MobileMe.

4. Manage spam false positives and negatives on Gmail

Because Gmail is filtering the messages, it’s important to remember to do all junk mail training on Gmail. If spam makes it to MobileMe, go to the Gmail account, find it in the archive, and mark it as spam. Also remember — especially in the beginning — to check the Gmail spam box for good messages incorrectly marked as spam.

One note about false positives. When you mark spam as good mail it is moved from Gmail’s spam box to the inbox. However, it won’t be forwarded to MobileMe. It must be managed on Gmail. It’s a small matter. After a short while, false positives will happen very rarely.

Because Gmail is handling spam filtering, remember to turn off junk mail filters in MobileMe (server side) and the Mac Mail.app. If you leave those active, it’ll become very confusing.

Final destination

Finally, the email has arrived at MobileMe. Configure both Mac Mail and iPhone to read email using MobileMe. It’s a standard process and very easy. Apple has tutorials on setting up MobileMe for iPhone, Mac and PC.

Follow the instructions for both Mail.app and the iPhone. Try sending test messages to the domain account “john.doe@example.com” and make sure it goes into MobileMe. You need to send test messages from some other mail account (like Yahoo or MSN or a separate Gmail account).

5. Manage your active mail on MobileMe — make it inbox zero

Now you have an place to manage your active email. Follow Inbox Zero. Keep it clean. Be ruthless. Remember that any deleted message can easily be recovered from Gmail.

One important setting to change in Mail.app and iPhone is how long it keeps sent messages and Trash. I always set sent messages to be deleted after 4 weeks and the trash after 1 week. Keeping your active mail clean makes it faster on the Mac and the iPhone. Be sure to save Drafts, Notes, Sent, and Trash on the server. These settings are under “Mailbox Behaviors” in the MobileMe account under Mail.app’s preferences.

Send email through Gmail

Now for the key to this mashup — sending email. Both the Mac and iPhone must be told to send all mail through Gmail’s SMTP server. What will happen when you do this is a tradeoff. You will send your messages twice.

The first time the iPhone or Mac will connect to Gmail and send the message to the final destination. The second time the iPhone or Mac will take a copy of the message and save it to the Sent folder on MobileMe.

I think it’s a small price to pay. Rarely do I notice a big problem. Even sending large files has never been a real problem. But you should be aware that each message is sent over the wire — twice.

6. Change SMTP server in Mail.app

We’ll start with Mail.app.

  • Open Mail.app preferences
  • Switch to the “Accounts” section and then the “Account Information” subsection
  • Click the drop down box for “Outgoing Mail Server (SMTP)”
  • Click “Edit Server List”
  • You should see the smtp server entry for MobileMe
  • Click the plus (+) sign
  • Description: Gmail
  • Server Name: smtp.gmail.com
  • Click “Advanced”
  • Server port: 587
  • Check “Use Secure Sockets Layer (SSL)” on
  • Authentication: Password
  • User Name: YOUR GMAIL USERNAME e.g. john.doe
  • Password: YOUR GMAIL PASSSWORD
  • Click “OK” to save the settings

Now change the “Outgoing Mail Server” to Gmail and turn on the “Use only this server” checkbox.

Now all email from Mail.app will be forced to use Gmail for outgoing mail.

7. Change SMTP server in iPhone

To Change your iPhone.

  • Go to Settings
  • Then “Mail, Contacts, Calendars”
  • Then the MobileMe account
  • Hit “Account Info”
  • Then SMTP
  • Hit “Add Server…”
  • Host Name: smtp.gmail.com
  • User Name: YOUR GMAIL USERNAME
  • Password: YOUR GMAIL PASSWORD

When you hit save, it should verify the information. Sometimes this takes a little while. It will return you to the SMTP server list.

  • Select the Gmail account
  • Switch the “Server” on
  • Hit “SMTP” at the top to go back
  • Select the MobileMe account
  • Switch the “Server” off

When you are finished, all SMTP servers should be off (including AT&T’s) and only the Gmail server should be active.

Sent Email

What happens when you send email? Although the MobileMe settings on the iPhone and Mail.app both claim to be sending as “john.doe@me.com”, Gmail rewrites the headers to indicate “john.doe@gmail.com”.

8. Hide your MobileMe account

Whatever you do, don’t give anyone your MobileMe address. The closest you want them to get to your real email is the Gmail account. If anyone finds your MobileMe account, they can bypass the spam filters. So keep it secret.

Nothing sent using this set up will show the MobileMe account. Unless you use me.com to send email. If you must use the web to send an email. Log into the Gmail account and send it from there. Reading and manipulating your email can be done on me.com.

Email aliases

I said before that Gmail can pretend to be from your own domain — like john.doe@example.com. Even the free version of Gmail can do this. However, Gmail will always include it’s own gmail based address in the headers. Microsoft Outlook will interpret the headers as John Doe <john.doe@example.com> on behalf of john.doe@gmail.com.

I personally don’t have a problem with people having my Gmail account. It’s not going to change anytime soon. All mail coming back will go through the spam filter. I’ve also found that once you set up a conversation with someone, they really don’t care what your day-to-day email address is. Most people have more than one address so it’s not a big deal.

9. Set Gmail to alias your domain

In your Gmail account, go to “Settings”. Under the “Accounts” section, click “Add another email address”. The process is fairly simple. After the new address is properly on the account, make it the default address by clicking “make default”.

From now on, all messages from Gmail will pretend to be from that account. Most programs will honor the personal domain when adding information to their own address books. So it works pretty well.

10. Use Google for Domains if you must hide the Gmail account

Finally, if you MUST have everyone believe your email is coming from a certain domain, buy a Gmail account.

Google offers a lot of personalized services for a minimal amount. The cost is $50 a year, per email address. You get more space and domain branded google applications. So for many people, it’s worth the extra cost.

Either way you go, it’s a great system.

Conclusion

This was a long post explaining a complicated set up. Once implemented, it’s a snap to use. The integration between iPhone and Mac is nearly perfect. Having a single, focused mail account makes managing current messages a snap.