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First off, i am not a developer and had no training in Civicrm. After 50 hours of getting contact into civi up to date. And creating contacts within orgs to mail (just seems insane civi isn't set up to email orgs to me) we finally sent out our first emailing to all our trust and foundation supporters.

Question is, how do i add reply's. We don't (for some UNKNOWN REASON) have civi connected to our outlook. Can i manually add these emails to a contact?

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See https://docs.civicrm.org/sysadmin/en/latest/setup/civimail/inbound/#autofiling-email-activities-via-emailprocessor where you can set up either a mailbox you can bcc that will add email replies to contacts, or you can set it up to pull from a specific folder in your own mailbox after-the-fact to do the same thing.

In terms of the earlier part of your question, when you say "contacts within orgs", Civi won't send to contacts who are employees of orgs, but if you set up Groups, then you can mass email to the group. See https://docs.civicrm.org/user/en/latest/email/mass-mailings-using-civimail/

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