For the small number of people who use Retrospective Record, I may have found the problem it’s been having.
To start off, I’ve written many posts about how it hasn’t functioned correctly since the Cubase 7.5.30 update, and I don’t think Steinberg has been able to figure out how to reproduce the issue. It’s so random and unexpected that there isn’t any one way to list how and when it happens.
However, I looked at the Change Log for the Cubase 7.5.30 update to see what had been changed. I noticed there was a fix for MIDI chasing controllers. In Cubase 8 and 8.5 I disabled all the chasing of MIDI in Preferences and have been having much more consistent Retrospective Recording. I still have issues where I’ll play something in and then hit the Retrospective Record key command and all the MIDI data is outside the MIDI region, but it does not happen nearly as often as it used to with MIDI chasing all notes and controllers. I’m not sure if it has to do with chasing controllers altogether or if it is only the “Chase Not Limited to Part Boundaries” and/or “Never Reset Chased Controllers”.
To sum it up, I believe something do to with chasing MIDI controllers is causing Retrospective Record to not function properly like it did in Cubase 7.5.20 and earlier.