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I have mail templates with placeholders for names (ex. Dear XXXXXX).

Is it possible to make apple mail check the content of my mail when sending and to stop an email from getting send out when it finds my placeholders?

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There are rules like this for Received Mail, but I have not been able to modify them for Sent Mail. I am also interested in the solution. – duci9y Sep 7 '12 at 13:18
According to StackOverflow answer you cannot access the outgoing mail messages via Applescript, which means that the chances to accomplish it in an easy way are low.. – nuc Dec 23 '12 at 19:13

Are you committed to using just

If you go to and search for Mail Merge there are a page of hits. At first blush, this one seemed to be right up your alley, but I may not understand fully what you are looking for. Claims to use your address book, and a composed message, and it does the substituting.

If your outgoing messages are batched, take a look at external software for sending out email. In my other life I use Mail Chimp to send out news letters, but there are many many others, with various features.

A final possibility is to abandon alltogether, and throw together a perl script that does the substitutions, and makes a call to /bin/mail for sending.

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