>A client has an OpenVPN server. I'm setting up remote users so they can connect to head office via OpenVPN. This is straightforward:
>
>- Each user installs the free/open source OpenVPN client
>- I give them a set of files which they install in a certain folder. These are certificates and configuration files and must be kept secure
>- Each endpoint has a unique set of files. So if a user has 2 endpoints they will receive 2 different sets of files. Unique files mean certs can be revoked if an endpoint is lost, stolen etc.
>- We have roughly 10 endpoints among 8 users. Most are Win10 PCs but there are a couple of MacOS machines as well
>
>I'm looking for ideas to simply and securely transfer file sets to remote users. What I've considered so far:
>
>1. Transfer via encrypted e-mail attachment with password sent separately (voice call or text). Some options:
>- ZIP file encrypted with ZipCrypto: can be opened natively in Win10 but ZipCrypto is no longer secure. Opening on a Mac seems to require a workaround in Terminal
>- Some other archiver such as 7Zip. 7Zip can securely encrypt archives (e.g. AES-256) but this requires installation of 7Zip on the recipient to be able to extract the files. Also 7Zip doesn't seem to be available for Mac; maybe some other archiver is cross-platform
>- Windows 10 can encrypt any type of file. But this is only available for Pro or higher; some users are on Win10 Home
>
>2. Use online/cloud storage such as OneDrive, SharePoint or DropBox. Using DropBox as an example I could:
>- Set up one dropbox with a common user name/password for all users
>- put all file sets in the dropbox. Each one protected by ZipCrypto and unique passwords
>- Users download the file sets for their endpoints. If they download other users' file sets that's not a problem, they won't have those passwords
>- Delete the files from DropBox once all users have theirs
>
>The only real downside to something like this is the users need to be given two sets of credentials: one for DropBox and the other for their ZIP file(s).
>
>Has anyone else had to deal with this and found an elegant solution?

I've setup an SFTP server and used WinSCP ftp client with some scripting to deal with stuff like that. The ability to create scripts was kinda the key.