Hi,
I believe something could be done with shortcuts, and I know I could create
an AppleScript to do this type of thing.
You would want to create a separate group in Contacts and then scan that
group in a for or foreach loop.
The part I don't know if Shortcuts can do is to add in personal information
in the content of the mail like:
Dear %FirstName% getting changed to Dear Jonathan,

AppleScript could certainly do that, but  I don't know shortcuts well
enough to know if it has the ability to substitute strings.

There are also commercial sites like constant contact and Mail Chimp that
provide these services and also make sure that you are following laws on
not sending spam and can also tell you if the message wa read or bounced.

Warmly,
Jonathan


On Mon, Dec 29, 2025 at 3:19 PM Kevin Gibbs <[email protected]> wrote:

> Guys,
>
> Remember when we used to use Mail Merge to send individualized postal
> mail?  Is it possible to do that with e-mail that is not sent from an
> e-mail list you moderate?  I want to send the same e-mail to four or five
> people without just putting e-mail addresses in the Bcc field and saying,
> “Dear All.”  I want each person to receive their own e-mail as if I’d sent
> it individually so they can respond individually not knowing that others
> received the identical e-mail save for the dear So & So.
>
> I’ve done some reading and it looks as though I can use a combination of
> Pages and Contacts.  But the instructions don’t appear crystal clear just
> yet.
>
> If anyone has ever done this, could you point me in the right direction?
>
> Thanks,
> Kevin
>
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