Techniques for automated suggestions for cross-context digital item containers and collaboration are provided, including analyzing digital items in each of multiple portfolios of digital items in order to determine similarities among the portfolios. The techniques proceed by determining similar portfolios for a first portfolio of digital items, and suggesting changes (e.g., additions, deletions, or alterations of digital items) based on differences between the first portfolio and the similar ones. Those changes can be accepted or rejected and applied to the first portfolio of digital items.