I had the same type of problem when attempting to decrypt using gpg2 on
a remote host, logged in via ssh from Ubuntu 18.04 client. Turned out
that GPG2 was unable to ask for passphrase via X-forwarding. I got it
working by disabling X forwarding ("ssh -x .." or "unset DISPLAY"),
which triggers a text-only pop-up asking for passphrase in the terminal.

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https://bugs.launchpad.net/bugs/1775923

Title:
  gpg can't access secret keys when logged in via ssh instead of desktop

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