I am trying to use the git-annex assistant to automatically sync photos from my Lightroom catalog on Mac OS X to a remote archive server. I hit a snag due to a race condition combined with some peculiar behavior of Adobe Lightroom: it dereferences symlinks and uses the name of the target when importing (see https://forums.adobe.com/thread/568863?tstart=0) I observe the following problematic workflow: 1. Files are imported using the original filename. 2. The assistant eventually moves the content to .git/annex/objects and creates symlinks to replace the originals. 3. The photos no longer appear in the Library, however Lightroom will not allow me to re-import as it thinks the files have already been imported and are duplicates.

I know a few other folks are using git-annex and Lightroom together, but I cannot tell if they are using the assistant or manually managing the annex. This implementation is for my wife who is not technical enough to use git on the command line so that's out of the question. It seems like direct mode is my best option for now, however, I'd like to avoid it since it's being deprecated. Is there some other option that I'm missing? Is anyone else out there successfully using the assistant and Lightroom together? I'd love some advice.