your upstream remote isn't getting updated with changes from dreamwidth.

Thanks, but I'm afraid I explained poorly. My upstream remote *is* dreamwidth. I put my dwu together when we first switched to git, so some of the names are different, but I've just checked and to all intents and purposes it's the same as the current version on the wiki, except that what that calls "dreamwidth" I call "upstream".

~/dw (develop)$ git remote -v
origin  https://github.com/swaldman3/dw-free.git (fetch)
origin  https://github.com/swaldman3/dw-free.git (push)
upstream        https://github.com/dreamwidth/dw-free.git (fetch)
upstream        https://github.com/dreamwidth/dw-free.git (push)

~/dw (develop)$ git remote show upstream
* remote upstream
  Fetch URL: https://github.com/dreamwidth/dw-free.git
  Push  URL: https://github.com/dreamwidth/dw-free.git
  HEAD branch: develop
  Remote branches:
    develop        tracked
    master         tracked
    release-1.11.0 tracked
    release-1.12   tracked
    release-1.13   tracked
    release-1.14   tracked
    release-1.15   tracked
    release-1.16   new (next fetch will store in remotes/upstream)
    release-1.17   new (next fetch will store in remotes/upstream)
    release-1.18   new (next fetch will store in remotes/upstream)
  Local branches configured for 'git pull':
    develop merges with remote develop
    master  merges with remote master
  Local refs configured for 'git push':
    develop pushes to develop (up to date)
    master  pushes to master  (up to date)
~/dw (develop)$ git status
# On branch develop
# Your branch is ahead of 'upstream/develop' by 540 commits.
#