“How can I send email to a group—from my iPad?”

This is one of the important workflow questions my new client Beth asked me when I first met with her last week. She needs to send announcements to a few small groups and she would prefer to use her iPad than her Mac.

Apple makes it pretty easy in OS X’s Contacts app to build and manage groups of contacts.

For contacts with multiple email addresses, Mail’s Edit Distribution List command enables you to set which address to use when sending mail to the group. And, in Contacts, select a contact and hold the Option key to see what groups have the contact as a member.

Group Dis-ease with Apple’s iOS Apps

Apple has not brought the same ease to its iOS Contacts and Mail apps. In Contacts, you can filter to see contacts in a specific group, but it’s impossible to create or add contacts to groups. In Mail, there is no way to enter the name of an existing group to send a message to its members.

The only way to send to a specific set of contacts is to have previously sent a message to the exact same group. Then, when entering a group member in a recipient field, Mail offers that group of recipients as a choice. But the offer shows the names of the recipients, not the name of a known group. This is far from convenient or intuitive.

I had not looked into group email on iOS in a long time. When I was originally curious, I only found Group Email! by Andrea Vettori.

This is a full-blown email client one would use instead of Mail to send email to groups. It currently gets four stars on the App Store, but investing in a separate email application is not a logical approach to me, especially at an $8 expense with no free demo version.

Useful Email Group Alternative

I read a tip that it is possible to add multiple addresses to an email field in a contact card in order to form and send to a group. I could not figure out how to do this manually, though, and quickly gave up.

When I met with Beth again this week, I searched again and was grateful to discover MailShot (4.5 stars) by Soluble Apps.

MailShot makes use of this hack and enables the user to create contacts that represent groups. The app creates a contact with a specified name and injects a single email field with any number of addresses.

Beth downloaded the free version, which is limited to three groups with up to five members each. The app is pretty simple to use and Beth and I easily created a test group with just the two of us as members.

We switched back to Mail, sent a test message to the test group, and immediately both received the message, just as if we had entered each of us separately as recipients. MailShot Pro, which removes the restrictions, was clearly worth $4 so Beth bought it (available as an in-app upgrade) and we were able to recreate her contact groups with ease.

Other Pros & Cons

Because these “group” contacts are stored in one’s iCloud, they also sync to multiple devices, so Beth can send to her groups from her iPhone as well without having to create them again. Soluble outlines several other key features, including the ability to forward a message to a group and retain original attachments.

The only con, I think, is that these hacked contacts-as-groups are incompatible with Mail in OS X. So, you would still need to use a properly formed group in Contacts to send messages from there.

Need Some Help Too?

Are you using Mail and Contacts to manage your email and address book? Are you keeping these data in sync among multiple devices, like your Mac and iPhone?

I can help you make use of these apps, get your data into iCloud, ensure you don’t end up with a bunch of duplicates, and teach you some useful shortcuts so you can be more productive with these tools.