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Mass Email Christmas Greetings without spamming

The person who sends out our company holiday greetings no longer works for us and its fallen to me to send out an ecard I created in Photoshop.  I'm IT support so this isn't my fortee but I want to be sure I don't get nailed as a spammer.  I was told I can send to 10-20 people at a time and be safe, does this apply to mail merge?  Is there a way to make the process easier, like create and save a draft and open and send it (ok this might be mail merge but I've no real experience with utilizing this feature in a workplace)?  

Also we don't really have a up-to-date contact list, that anyone can find, so I copied the emails from the messages sent last year.  This poses a problem with new contacts.  Is there a way to check or track who I've mailed to with a massive master list?

Any help is greatly appreciated!
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HSI_guelph
Asked:
HSI_guelph
1 Solution
 
Bill BachPresidentCommented:
I think the answers to these questions depend on several factors:
1) Are you hosting your own SMTP server?
2) If not, does your ISP have any maximum sending limits?
3) Are you sending Emails to people who already do business with your company?
4) Do you provide them with a way to opt out?

The BEST solution is to add a mailing list feature to your web site.  This will allow users to sign up on their own, and if you use a double-opt-in solution (you have to also follow the link to make your registration permanent), then you should not run afoul of any spam regulations.  Again, the SMTP gateway host is likely to be a big part of the answer, so contact your ISP or hostiong company, if needed.  Of course, users can always flag a message as spam just because they don't like your message, and if enough do it, then you may still get flagged as a spammer.  I doubt most people do this with holiday greetings, but I could be wrong.  

With ONLY the info already posted, I would simply make up a small email message, then automate with a tool like KeyText.  This keyboard macro tool can be used to extract Email addresses from an Excel spreadsheet, then build an Outlook Email directly to each recipient.  As it works only as fast as your local machine/keyboard, it won't be able to send too many messages per second to run into the spam issue, but it may take it all night to run, too.
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HSI_guelphAuthor Commented:
Cool, thanks for the reply!  I'll just do it manually and track it to be sure I got everyone.
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