Mail.app and Address Book being stupid
Hawk Wings reader Leonardo Burci emailed today to tell me something about Address Book and Mail.app that I didn’t know.
He writes:
Create a Group in Address Book. Add people containing valid e-mail addresses plus a person without an e-mail address or with an invalid e-mail address.
Create a new email. Choose your Group as recipient. Send. You get an error saying something like “mail could not be sent using server xyz, etc”. It doesn’t tell you the real reason why the email couldn’t be sent. It should.
Problem: a Group in the Address Book might consist of people and companies with and without e-mail addresses. This group might be used for sending letters, faxes and e-mail. Mail.app should handle such a recipient list intelligently.
Solution: Mail.app should inform the user about missing and invalid e-mail addresses and should give the user a choice whether to send the mail to the recipients with correct e-mail addresses or not. If you do send, it should give the user a list of people and companies that have no or invalid e-mail addresses and that were therefore excluded.
He’s right. This is not the behaviour of an Operating System that “just works”.
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- Emailing a Smart Group in Address Book
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- Address Book and nicknames: three work-arounds
- Setting a default email address in Address Book
Tags: Address Book, Apple Mail, bugs, error message, groups, invalid email addresses, mail.app

June 1st, 2006 at 12:27 am
I’ve had this problem a lot since coming over from Eurora a couple of years ago. (In addition to only being able to send to one email address per address book entry)
A simple solution is to make a new smart group with a rule-set like “email contains @” and “email contains .”, and use that list as the basis for email groups. Unfortunately Address Book doesn’t have an option to select “group is …”. Kinda stupid really.
June 1st, 2006 at 1:54 am
I just tried this with Mail.app on Tiger 10.4.6
When I type in the name of the address book group and hit ‘tab’ to go to the next field, the group is expanded to show all the addresses I am sending to.
When I click send, it says “[name]” does not appear to be a valid email address. Please check the address and try again.
This is for a contact with no address.
If the address is just bad – i.e. incorrect, I wouldn’t expect Mail.app to be able to tell. Any bounce messages you get are from the mail server and not the responsibility of Mail.app.
I just tried sending it without first expanding the group members and it does the same thing.
With more than one bad address it seems to only tell me about the first bad addres.
June 1st, 2006 at 4:04 am
I have seen this before too and was initially as baffled as anyone else. The message from Mail I get seems to suggest that the mail server is not available and it offers to use another one (I have several mailboxes with different servers plus postfix enabled). Definitely a Mail.app bug
June 2nd, 2006 at 7:26 am
This is also the case when you have a bad email address in the group… not sure how but Mail does not let you send the message to anybody in the group until you track down which address is bad…
Seriously annoying when you have 20 people and one of the addresses is bad…
I do the fifty/fifty rule… cut out 50 percent of the addresses… if it goes then repeat with the addresses you cut, if it doesn’t go then take that list and cut… you get the drift ;-)