Yes, technicallly, they should reach their mailbox.
Just make sure that all the mails are not sent using same IP address.
If you don't have static IP than send him a lot of bulk mails, switch off your router and turn on to get new IPand do the same.
Try different subjects for sending your mails so that filter cannot be applied.



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and do the same.
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you want to try your luck... ur wish....
