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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