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If you work inside a company and are just allocated the task of bulk emailing then you already have lists and procedures to follow. You should stick to those procedures and amend them if need be, because you'll get the blame if anything goes wrong. If you work on your own it's even more important to be careful.
Firstly it is much better to use a Linux server for emailing and if you have admin access to such a server then it's a fairly standard procedure to set up one or two mailing programmes into which you can feed varied content and varied lists of recipients. The software should obviously never show anyone's email to anyone else - each item should be sent on its own.
Make sure that you keep several backups of the list of emails being sent out and make sure that until you have run out of recipients you ensure it does not allow you to email anyone anything more than once. If you are organised you can minimize the attrition which reduces the number of customers you gain.
Keep logs of the mailouts and ensure you review the logs regularly every time, in case anything ever goes wrong. And naturally you will end up with a list of who to NOT email - ensure that this list is properly integrated into everything so there is not a chance that anyone who really shouldn't be mailed ever gets mailed.
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