So I have a legit mailing list of about 500 people who I need to email at least once a month, sometims three, or four times.

Does anyone have large mailings like this?

My main question is, where does "the internet" consider it spam, and where does it consider it legit.

Do I just send it out of Outlook CC? Or is there a better way to handle it.

Hi WillStein,
You might want to start here with some info on the Can-SPAM Act for Commercial Emailers. I believe this will answer any questions you might have on this subject.

Hope this helps,
DianeD

thanks diane!

just use outlook or gmail, in gmail you could seperate emails with ; . u could write an app to do this with a big lis tof emails.

i hope im not supporting a spammer!!!!!

I decided to use PHPlist.
It's very confusing, lots of bugs, but has huge potential.

I would reccomend not listing all the e-mail addresses into your usual e-mail client. The list will appear on everybody's message and some people might not be too happy finding out that their address has been mailed to 499 other people and is therefore more likely to end up on a spam list.

There's also the issue of your message being wrongly treated as spam by anti spam filters. Also, if you decide to send messages in HTML Format, bear in mind some people's e-mail clients either don't read HTML at all or block embedded images so provide a link to an online version or provide a text only version.