I am also having this problem, or more generally that Sync just stops before finishing the first sync. My setup: iMac at home, MBPro in office, RaspberryPi w/ ext HD at home. MBP in the office is always running, in order to correctly sync with the iMac; but I would like to change that, hence the RB. Sync on MBP is 1.4, the others are 2.0; in total about 35-40 GB to sync. What happened is that the RB started syncing and moved to about 28 GB but then stopped. It now very often shows that it is indexing, but it does not sync the remaining files, and it uses 100% CPU. If I create an empty file on the RB (using "echo>foo") then that gets synced through to the others, but if I create a file on the iMac then syncing does not happen, or only after a very long time. I read in some other post that filenames that contain special characters can be a problem, and I have many of those in Keynote presentations, as well in other Software-generated files, so I can not change that. Is this issue confirmed, and could it be a reason for my problems? In my case the files that don't get synced also have normal filenames, but maybe there are so many others that sync gets confused... I did a test regarding that and made a second sync folder that only contains my Keynote presentations. It is in total about 3.2 GB on my iMac, but only 2.2 get synced to the RBPi (in this case it does not sync to the MBP, so only Sync 2.0 devices are involved). When I checked progress during the first sync I noticed that sync basically works down the file/folder list alphabetically. I have several subfolders for the past 10 years, and they get synced starting with the lowest numbers. The syncing stops at 2014 (of course... ). Sync worked flawlessly between the two macs, but not with the RBPi - I am worried that this will scramble my files somehow, and that the Pi will make Sync delete files or something. Does anybody have an idea what is going on here?