A (hopefully simple but possible tricky) Mail question

[mike1mike2mike3]

I would like Mail to prompt me when addressing an email under these conditions, but don't find a way to do it. I imagine it's not a unique question, however. The scenario:

I have several contacts with whom I have both professional and personal relationships. I have multiple emails for each (e.g, a work email and a gmail account). Some have asked me to keep work emails to the work address, and vice versa. I tend to use the autocomplete in the Mail address field, and sometimes (usually!) forget so it picks one for me when I type their name. Often the wrong one.

The functionality I am looking for: I would like to be prompted whenever I type a contact that has multiple email addresses, and forced to select which one I use, rather than letting Mail choose for me.

Any thoughts on how to accomplish this?

Thanks!
mike

 

[Pndrgnsvc]

Not a solution per-se, but perhaps a work around and worth a try...

Example: For Mr. Henry Higgins:
1. Create two distinct Contact cards. One where the name is Henry Higgins Home, and the other is Henry Higgins Office (with the appropriate email addresses of course).

2. Then when addressing your email, Mail should ask which Henry Higgins you had in mind.

But even that won't be a perfect solution, so be watchful, especially at first.

If you give that a go, please advise of your results.

 

[satcomer]

First you could have each contact in AddressBook and also in Mail's menu item 'Window' and select "Previous Receipts" because it also uses these too.

 

[BrianBaughn]

It's not there by default, but there's an "Address" button that you can add to the "New Message" window that might solve your issue.

Create a New Message, right-click (control-click) the toolbar, select "Customize Toolbar...", then drag the Address button up there. From then on you can click the button, type the recipient's name into the search, pick an email address, then click the "To:" button.