How to send just a few emails at a time to a large group in Outlook 2010

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Outlook version
Outlook 2010 64 bit
Email Account
POP3
Hey all,

Using Win7 64 and Outlook 2010... I have a large group (over 500 contacts) that I need to send a single email to a couple times a week. If I make the email and select all of then and try to send it, I get a response back from yahoo saying it's spam or something like that and the message does not get sent. If I sit here and select 10 contacts at a time and just keep resending over and over it will work fine.

So, is there a way to select the entire group and send the email but only send to like 5-10 contact every 10 seconds or 1 minute or something like that?

I was looking at the Delay feature in Outlook but it just delays the entire message to everyone and ships it out all at the same time like usual.

OR

I was then told that Gmail will allow 500 outgoing emails without hitting a spam filter so I created a new gmail account, I set it up in Outlook, and can send the emails however the "From" email that everyone sees is the Gmail account and I need it to show my yahoo account. How can I basically mask the actual FROM with my other email address?

Thanks all!
 
I'd use Mail Merge - this will send individual messages to each person and are less likely to be tagged as spam. You can use a utility such as one at Mass Mail Tools for Outlook - Slipstick Systems to throttle the sends to a specific number per minute.
 
I'd use Mail Merge - this will send individual messages to each person and are less likely to be tagged as spam. You can use a utility such as one at Mass Mail Tools for Outlook - Slipstick Systems to throttle the sends to a specific number per minute.

Are you referring to Mail Merge in MS Word?

And if I use this and still process through Yahoo, wouldn't I still be getting the return Spam mail and block the email from going out?

Or are you saying to use MS Words Mail Merge to help cut down on going into peoples Spam and also use the Mass Mail Tools to limit the sending so it's all good to go?
 
You need one or the other - if you don't need to throttle the sends, schedule the sends, or add attachments, you can use mail merge. If you need more control, one of the merge tools will be a good investment. The mass mail tools will do a mail merge - one address per message - and that will reduce the chances that the message is marked spam.
 
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