Development of a SharePoint to OpenWebUI Synchronization Platform
GentleShare: SharePoint → OpenWebUI Synchronization Platform
Development of GentleShare, an administration application designed to synchronize SharePoint content with OpenWebUI, as part of an enterprise AI assistant powered by internal documents.
Between April 23 and 28, 2026, the project evolved from an initial Laravel base to an application structured around Laravel, Filament, MySQL, Microsoft Graph, and OpenWebUI. The goal was no longer just to trigger synchronization, but to build a usable platform: folder tracking, file management, asynchronous synchronizations, processing history, visible statuses in the interface, and improved error observability.
Significant work focused on improving the reliability of long-running synchronizations. SharePoint synchronization was moved out of the traditional HTTP cycle and delegated to Laravel jobs, with persisted runs, progress tracking, and an interface capable of clearly indicating the last executed process. This evolution prepares the application for real-world volumes by avoiding issues related to web request timeouts.
On the OpenWebUI side, integration was strengthened with better handling of processing times, functional warnings, and edge cases such as files with no usable content, excluded extensions, already existing files, or zero-size SharePoint files. The application now provides clearer insight into what has been processed, ignored, or rejected, file by file.
The project was also realigned for cleaner Azure deployment: corrected GitHub Actions workflow, clarified application packaging, revised nginx/startup configuration, identified environment variables, and overhauled technical documentation. README, architecture, development, product, and roadmap files were recreated to reflect the project’s actual state.
Summary: GentleStacks now has a consistent application foundation to manage SharePoint–OpenWebUI synchronization, with a more robust architecture, better process traceability, and documentation aligned with real product usage.