I just purchased SketchUp, which offers cloud storage via Trimble Connect. I can see my models in Trimble Connect on both the web and desktop versions but they don’t sync. When I make changes in Desktop, I don’t see them on Web and vice versa.
Are you just clicking on Save in the Desktop version of SketchUp? If so, that saving is done locally. You need to Publish the model to your Trimble Connect storage by clicking on File>Trimble Connect>Publish Model or >Publish As…
Generally it is advised that you save and work on locally saved files and only upload/publish to the cloud.
When you want to sync your project data, you need to consider what location is gonna act as the ‘main’ placeholder, the cloud or a folder(structure) on your machine. While the cloud could be used easily with he premium web based modeler, you need to use the (shipped when installing) extension Trimble Connect (In the desktop version or ‘client’, go to View->Toolbars and enable Trimble Connect.
Caveat, you need to open a new (empty) file first, then, you can open a file from the cloud (File->Trimble Connect->Open File
If you are more of a desktop kind of person and like to work with data that is stored on your local machine, you can still have everything synced without bothering to use the extension, you can download the Trimble Connect sync app from your app’s page, accessible through the browser, web.connect.trimble.com, sign in and click on the little raster icon in the top right.
Install, create some projects in the cloud and have it synced automatically or manually.
Check this thread, where a method is shown to have your libraries synced: