When changing the rotation strategy of an index set, Graylog will adhere to that configuration starting with the current write-active index but not for the existing ones.
When changing the retention strategy (close, delete; number of indices) of an index set, Graylog will adhere to that configuration for all indices, e. g. if you configured to keep 20 indices before and now configured 10 indices, Graylog would delete (or close) all indices over that number.
The retention runs over all indices (and not just every 6 months, but every few minutes). Depending on your configuration, the oldest indices will be closed or deleted until the number of configured indices has been reached (e. g. 365).