One feature that Gmail is lacking is the ability to send an email to multiple addresses for a single contact when using groups. Say you have a soccer team, each child has two parents with seperate email addresses. You put the child’s name in your contact list, add each parent’s email address, then create a group to send mass emails to your entire team. Gmail only includes the first (primary) email address per contact. You need to include both email addresses. Previously, you needed to add each child in multiple times so that each email address is seen as a primary. I have a simple fix to keep your contact list from growing too large!
In the first email line type in your first address. Follow that address, in the same line, with >, < then include your second address. It should look something like this firstname.lastname@example.org>, <email@example.com. I know, Gmail doesn’t like that when saving, but do it anyway. When Gmail adds your contact address to the To: line, the address is placed in brackets and seperated by a comma. In this way, you’re tricking Gmail into seeing two different addresses in the To: line. Gmail will automatically open the brackets on the first address and close the brackets on the second, or final. You just need to put the middle part in there so that both addresses are recognized as valid when the email is sent. Now, add your contact to the group you need and you’re all set.
Go ahead! I know you want to try it. Add yourself as a contact, add two emails for yourself (I know we all have a bazillion). Click your name from the contact list and email yourself.