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How to change the directory of files to attach

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In my shop, the seller must send an e-mail to the customer/customers.

And to this e-mail must add the file (prepared by me a contract that I have uploaded to the server: wp-content / files).

And when he press “attach a file”, the files can be only add from “my computer”, “flash drive”, ect…

But as an administrator, I want the files have been added to the E-mail from the folder created by ME and not from anywhere.

How can I do this?

and the second question:

How to make the drop-down list of registered users, to whom I want to send e-mail (a choice: one, two, five, all) automatically added to the list, not manually


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