What's the best way to send mass personalised emails using Mac Mail?

You do not understand my point about spam - the issue is that other services (like Google, iCloud, corporate email servers - your recipients email servers) may flag your mail as spam depending on how you send it. There are issues to take into consideration (like testing how it looks in many email clients - they all have their own quirks). A personal email account is not whitelisted for mass emailing. Do you have your own domain to send from?

You can use the free Mailchimp plan for 2000 subscribers & 12,000 messages per month.

http://mailchimp.com/pricing/entrepreneur/

Look around for better prices - Mailchimp has a good reputation & is worth testing.

Apple Mail is simply not designed to be a 'bulk emailer', you could probably build your own system out of Applescripts for Apple Mail, but that will take a lot of work & is prone to errors. Other mail apps (like Microsoft Outlook) can do bulk 'mail merges', but you may see what I mean as your messages fail to send or return to your Mac.

You keep saying 'it should be easy' - but you are finding it isn't the case, I suspect that is because the problem is larger than you are imagining.

See if any other users here have a better suggestion, I think this is a 'solved problem', there is no need to make it more difficult than you need.

You must also consider the limits most ISPs have on sending out mass emails. They are in place to discourage spammers. If you use iCloud, here are the maximums:

Mailbox size and message sending limits in iCloud - Apple Support

Check with your ISP.

In all honesty I suggest you find a good online service to do it for you…

http://mailchimp.com

Or one of the many others.

These services have the ability to handle bulk messaging. Email servers will block your messages if you appear to be spamming, there are many issues to deal with (failed addresses, bouncing mail, handling requests for subscribe/ unsubscribing…). I suspect it is more trouble than it is worth to manage it all yourself.

I feel your pain. I run a residents association (only 250 members) however it seems to be an un-solvable problem on the mac. I switched to mac only 12 months ago and previously I could do a mail merge using office (Outlook, Word and Excel). This should be a simple thing to achieve with mac mail, pages and numbers, but apparently not. For no good reason that I can find (Worries about spam not-withstanding).

1. Most ISP's have limits.

2. Apple Mail app was not designed to be a mass mailer.

3. Check with your ISP and then send out 10 emails @ 25 (or whatever their limit is) recipients each (copy/paste the content).

Thanks babowa

That is all well and good. However, you cannot personalise each email with the member's name. Further, you have to use BCC field and that can trigger spam filters not to deliver.