I am in need of encryption software that would keep files encrypted on the cloud as well as local on all machines.

Here is what I'm looking for:

Downloaded files saved to a particular folder on a Windows 7 or 8 machine would automatically be encrypted (after a prompt for passphrase).  Ideally, this folder would be in a Dropbox or Google Drive folder, or on a thumb drive.  No record of the unencrypted file would remain on the local PC (I am not worried about pieces of it on swap).

I would prefer that the files are individually encrypted with the same passphrase, rather than added to one large file which is encrypted.  I don't want the cloud storage to have to recreate the whole folder, and I don't want a bit error to trash all of my files.  The file names do not need to be encrypted.  

Since I will be the only user in the foreseeable future, a symmetric encryption scheme would be fine.

From the cloud (preferably) or thumb drive folder, my ruby program running on Mac OS X would edit the files.  I would also want to be able to decrypt the files to view in a text editor or other software, after which I would secure erase copies of decrypted files - again, no unencrypted files on the local machine other than in swap.

This is the ideal.  An alternative would be to send the files via https to a web server on the Mac (which could handle encryption in a local Mac environment) and the secure erase the files on the PC.  If I did this, could I send the files unencrypted (since https will encrypt them while they are on the internet)?

True Crypt appears to be close to what I want, but it is discontinued.  I don't know if I could use something like gpg, since I don't have admin privileges on the PC.

-Dan

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Dan Martin, MD
GP Hospital Practitioner
Computer Scientist
ummar143@shaw.ca
(204) 831-1746
answering machine always on