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- GPG on GMail (Mailvelope Chrome extension) - only for important mails and obviously, only with people who have it on the other end

- Truecrypt (always had it)

- Boxcryptor on Google Drive for all important docs

- Paid VPN

- TOR (if you think this is for encrypted comms, you're wrong)

- Keepass for password storage (key file in boxcryptor)

So on and so forth

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Do you think Boxcryptor is more useful/easier than putting a truecrypt volume inside your dropbox folder?

I can only speak for the old Boxcryptor version which is actually a slightly feature limited, proprietary implementation of encfs. TrueCrypt uses a container, encfs instead encrypts on a per file basis. So a small change is more easily to sync, at least when the sync service doesn't use binary diffs.

Exactly this. I evaluated both options for a while before settling on individual file encryption -- faster and cheaper sync.

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