When using git as the VCS, if I committed something on my local onto branch (master) and then switch to a review branch and run arc land. Both changes will be pushed to the remote.
When I looked at ArcanistLandWorkflow.php it looks like the only case we will set $local_ahead_of_remote is when git pull --ff-only --no-stat fails and it is a git/svn repo. Both conditions do not apply in this case.
More than that, using git pull assumes that the onto branch is setup to correctly track the remote onto branch which is not always the case.