As the container for deploying features, releases should automatically include the initiatives for the constituent features. As it stands now, I need to look through all features and manually add the initiative to the release. This is particularly challenging when trying to conduct management reviews from the portfolio, and having to double check / manually update the releases to reflect activity against the initiatives.
We currently have the ability to link both features and releases to initiatives. We generally suggest that when linking a release to an initiative, that this should be based on the general theme of the release. With that in mind, we do understand that some also do provide these links based on the features which make up the release.
At this time, based on community usage and feedback and current priorities, we are unlikely to make updates in this area to automate this rollup. We hope you can understand.