If you need to GPG sign all commits SINCE a particular commit on the current branch, you can use the following instead:
git filter-branch --commit-filter 'git commit-tree -S "$@";' <COMMIT>..HEAD
Where <COMMIT> is the commit id (e.g. abc123e5).
This has the added benefit that it does not disturb the commit metadata (including commit date). The commit hashes will change, though (since it's a digest of the contents of each commit, and a signature is being added to each commit).
If you also would like to stop getting prompted for your GPG passphrase on every commit, also see this answer:
https://askubuntu.com/a/805550
NOTE: Switching from gpg to gpg2 for GIT signing will require you to re-import your private key in GPG 2.