Techniques are described herein to generate a custom share sheet. The custom share sheet comprises one or more shortcut controls to share a content item using one or more corresponding contact-avenue pairs. A contact-avenue pair includes a link sharing mechanism and contact information for one or more recipients within the application or application protocol that uses the link sharing mechanism. The contact-avenue pairs are generated based on the share history of the particular user sharing the content item. Shortcut controls to sharing a Content Item Are primarily generated based on local share history. These shortcut controls are ordered based on contact-avenue pairs that were most recently used to share a content item. Shortcut controls to sharing a Content Item Are secondarily generated based on cross-platform share history derived from content items stored in cloud storage. These shortcut controls are ordered based on contact-avenue pairs that were used to share the most content items.