*Update* There are now several apps that make emailing large groups easier. An example is the free app ABContacts Lite.

One of the missing features of the iPhone’s Mail app is the ability to create a group of email contacts and send an email to that group. For example, let’s say you’re at the hospital, your wife just had a baby, and you want to send an email to a large group announcing “It’s a boy!” You’d have to enter each contact in one by one—a tedious process.
There is a somewhat imperfect workaround that involves a little preparation. The answer lies in creating a draft email. Here’s how:
Emailing Large Groups With the iPhone
1. Open the Mail App.
2. Tap the compose email button at the bottom:

3. Add contacts in the To: field by either tapping the plus sign or simply typing the first few letters of the addresses.
4. If you want, add a subject line and text in the body.
5. Tap the Cancel button in the top left corner.
6. Tap Save:

You have just saved a draft version of that email in the Drafts folder. You can check it out by tapping your email address button in the top left, then tapping the Drafts tab.
When it’s time to send it, simply navigate to the same Drafts folder, select the email, enter in any new information, and hit Send.
How to Send Subsequent Updates to the Same Group
1. Tap the Sent folder (it’s directly underneath the Drafts folder)
2. Tap the email you sent to the group.
3. Tap the arrow icon on the bottom right:

4. Tap Reply All.
You’ll notice that the group of contacts will now appear in the CC: field, and your own address will appear in the To: field. That’s ok, the new email will still be sent to everyone, and you’ll get a copy sent to yourself as well.
It’s recommended you change the subject line, as the text Re: is automatically added, making it appears as if it’s a reply. That might be confusing.
What About Pictures?
Unfortunately, if you snapped a picture with your iPhone, you can’t attach it to the draft email. With the iPhone, photos are attached only by going into the Photo app first, choosing to email the picture, and starting out with a fresh email.
One possible workaround is to upload the picture to Flickr, and then point people to your Flickr account in the email. There are two ways to upload photos to Flickr: email and apps. Here are instructions on emailing iPhone photos to Flickr. There are also apps that let you upload to Flickr form your iPhone: Mobile Fotos ($2.99 , App Store), Darkslide Premium ($3.99, App Store), and Reflections ($3.99, App Store).
Check out all of our posts on iPhone Tips.

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#1 by Telmo on May 5th, 2010
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It works!
Thanx
#2 by Tanshin on May 12th, 2010
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Theoretically, you can also copy and paste a photo from the Photos app. This should address the problem temporarily, but let’s hope Apple suppourts groups in OS 4.0
#3 by Mike D on August 9th, 2010
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I can’t belivie I never thought of that.
Thanks,
I love my iPhone but I can’t believe they didn’t fix that in iOS4.