Just one more thing!

Of course, it may be difficult to find a user-experience that works well for 
yourselves and your users. 

An even more generic approach is to ZIP the files with encryption. This has an 
added benefit of allowing you to send packets of data, not just individual 
files. I don't know how many software clients offer this, but 7-zip (7z) for 
Windows on the desktop makes encryption easy enough: https://www.7-zip.org/

You can:

- Add file to archive -> Select "Encryption" -> Provide a password -> Save

And like the previous example send the zip and send your password securely 
another way. Your user may need 7z - my default Windows client doesn't play 
well with the encrypted zip but maybe others have a better experience?

More info: 
https://hilfe.uni-paderborn.de/Dateiverschluesselung_mit_7-ZIP_unter_Windows_10/en

A word of warning about ZIP is that you will likely want ensure your filenames 
don't contain sensitive information as the file lists within the zip remain 
visible even when encrypted: https://superuser.com/a/70325

NB. You may also want to look for a password generator to generate randomized 
passwords you send to anyone to increase security further.

All the best,
Ross

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