Silhouette has released an update that should fix most of the issues you have been having with the cloud.
To get the update, click here.
From the release notes:
V3.8.113 – 25 Oct 2016
25 October 2016
- OSX Sierra support (Mac)
- Silhouette machine drivers installed upon installation of Silhouette Studio® (Windows only)
- Library Cloud bug fixes
- No longer silently fails if it takes > 30 seconds to upload designs to the cloud
- Retry mechanisms implemented to keep going even after a connection time out
- Changing case-sensitive files / folders in the Cloud no longer causes a concern
- Other miscellaneous fixes applied
- Deep Cut Blade option now available for CAMEO3
- Removed keyboard shortcut actions while text style scroll window has focus
- Glitter Heat Transfer Material added to list of available materials