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How can I send an encrypted email in gmail or Outlook?

What email applications support encryption? Can I send or receive an encrypted email or attachment via gmail? What is recommended to send encrypted email?
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for gmail to send / receive encrypted emails add-ons are available

outlook natively supports secure email and for that you need digital signature (public key) of receiver and vice versa
Comodo provides you digital certificates for secure (encrypted email) for free of charge
process to protect email in outlook:
EirmanChief Operations ManagerCommented:
All you really have do is attach an encrypted file containing a Word or text file.
It's fairly easy to crack MS Word encryption - Use a ZIP (or better a RAR) file to encrypt your files.
WinRar encrypted files with a decently long passphrase are uncrackable with today's technology.
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