I think you should go through the trouble of understanding and using public key encryption. This is the best long term solution. It looks like https://www.gpg4win.org will allow you to create a key and encrypt stuff. After you encrypt the documents, just paste 'em into an email. Of course, Alex will also have to have a public key that you encrypt to. So, he'll have to set up GnuPG as well. (It's super easy on Linux. Or, at least, it's easy for me :-). ) > From: Flora <http://www..family/~flora> > Date: Tue, 1 May 2018 20:52:22 -0400 > > I'm wondering if you have an opinion of Firefox Send. > > https://send.firefox.com/ > > Alexander is in the process of completing his application for summer > employment at UMASS and needs his birth certificate. It seems like I am > constantly running into this problem. > > Thoughts?