LibreOffice Version: 6.0.2.1 with Spanish Translation. I've been trying to sign a document with my software X509 and with my Spanish Identification Smart Card (Known in Spain as DNIe)(PKCS Module). If you want, tell me and I will open another bug.

Hi maybe the bug is related with the cryptography module of LibreOffice in Mac. Gebietsschema: de-DE (de_DE.UTF-8) Calc: group I can confirm above behaviour on two different machines. Both PATH and /etc/paths.d seem to contain the right path.

I assume it has something to do with the path to GPGTools, but no idea how to chase this. Starting LibreOffice via 'open /Applications/LibreOffice.app', or 'open file.odt' or '/Applications/LibreOffice.app/Contents/MacOS/soffice' does find the key. Verifying existing signatures yields to an error message with 'broken/unknown signature'. Regular X.509 certificates work (from within Thunderbird's profile). This is both visible in the settings when no predefined PGP key can be chosen, and in the signature dialog, when no PGP is offered. No PGP keys/signatures are found when LibreOffice is started from Spotlight or directly via double click on ODF file. Running LibreOffice 6.0 on mac OS 10.13 with GPGTools 2017.3.

Gpg keychain access for mac