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SharePoint is considered as a robust platform for collaboration where users can conduct various diverse operations and further store them in one single location. But, the intricate complexity of the system proves to be frustrating for even the most experienced users. SharePoint bases itself upon six essential features - business intelligence, business processes, enterprise content management, search, portals, and collaboration. Moreover, most of these features are inter-related with each other, thus making it a difficult task to identify and segregate the issue for users, developers, and administrators. Troubleshooting problems in such a complex and intertwined environment demands the administrator to be proficient and experienced in isolating SharePoint errors, which can be gained from practice and patience. Let us browse through some of the usual challenges encountered by users collaborating through SharePoint and devise methodologies so as to troubleshoot those.