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I manage IT for a large organization with over 2000 people. The administration would like to send an email (often with up to 5 word document attachments) about once per week.

They also want to categorize people. For instance, about 40 people are "teachers," about 1800 people are "students," and about 10 people are "board members." They may send an email to any combination of these categories.

Here's what I have tried: I bought a server, installed Ubuntu server edition on it, and wrote a python script to send out their emails. However, pretty soon, mail services such as Gmail and Yahoo began to treat the mail I send out as SPAM. I'm guessing this is because I am sending an email with 2000+ people in the "bcc" field. Maintaining this server also takes a lot of time.

How do I set up a mailing list for over 2000 people? Must I defer to paid services?

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closed as off topic by Michael Hampton, Brad Patton, Simon, 8088, Joe Taylor Apr 24 '13 at 17:45

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There is no need to reinvent the wheel. Since you've already installed Ubuntu Linux, I suggest using something like the following:

  1. Install Postfix or any other MTA. Whatever comes with your Linux distribution is probably fine (Postfix, Exim, even Sendmail).

  2. Install mailing list management software. For example, Mailman is quite popular.

  3. Then you create appropriate lists, e.g. "students", "teachers", "board", etc., and send email to the list address. The mailing list software is responsible to email individual users, process bounces, can handle subscribe/unsubscribe if needed, etc.

Please be warned: configuring and maintaining an email server looks easy on the surface, but in fact it's an arcane art and there are many subtle gotchas. Outsourcing this task to third-party services, like MailChimp, is not such a bad idea. Not sure if MailChimp has right set of features for you, but there are many mailing list services, and considering that you have very low-volume list, it should be quite cheap no matter which one you choose.

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