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How to Symmetric Password Encrypt a File on Mac with GPGTools
GPGServices and then Decrypt it on Windows with Gpg4win Kleopatra

Applicable software versions:

GPG Keychain Access Version 1.1.3 (601) for Mac

Gpg4win Version 2.2.1 for Windows

Kleopatra Version 2.2.0 for Windows

Mac OSX Version 10.9.3

Windows 8.1 Pro N


– On the Mac, Install GPGTools for mac

– On the Windows PC, install Gpg4win

Downloads can be found on, or linked to from the GnuPG website:


Steps to encrypt the file on Mac:

– On the Mac, on the file wished to be encrypted, choose:
(control+click) -> Services -> “OpenPGP:Encrypt File”

– On the “Choose Recipients…” Window that comes up, enable
the “Encrypt with password” checkbox, disable the “Add to
recipients” checkbox and click OK.

– The “Pinentry Mac” window appears. In the “Passphrase”
field, create/enter (and remember or safely note) a passphrase.
Re-enter it when prompted again.

– This will create an encrypted copy of the file, next to the

Then Send/transfer the encrypted file however you like to the
Windows PC.

Steps to decrypt the file on Windows PC:

– On the Windows PC, launch Kleopatra and choose “File” ->
“Decrypt/Verify Files…”

– Browse to the wished-to-be-decrypted file and choose “Open”,
and in the “Decrypt/Verify Files” window that appears, choose a
destination folder and click the “Decrypt/Verify” button.

– A “pinentry” window will come up, prompting to enter the
passphrase that was used to encrypt the file. Enter the passphrase .

– The contents of the wished-to-be-decrypted file will become
decrypted into the destination folder.


“How to Decrypt Using GPG”:

“GPG Encryption Guide – Part 4 (Symmetric Encryption)”:

“18 Signing and encrypting files”:

Other resources:

“How to encrypt and sign text or files with GPGServices?”:

“Decrypting a file using GPG4Win (Kleopatra)”:

*2014-12-05 edit: previously published at

[2020 edit: Moved to: https://investorworker.com/2014/... .html.]