There was along running thread about this a while ago, and I was never able to reproduce a problem where searchback didn't work as expected on
playback except in a very unusual case where the MIDI clip had been slip-edited so the clip boundary was earlier than the first event in the clip.
It was also discussed that the "shadow" of a controller disappears further into a piece (like 100 measures later) but the effect of the controller searchback is still audible - it's just a display issue.
And it was also discussed that searchback is strictly a
playback function, and doesn't work when bouncing a section of a track where the selection doesn't include the most recent controller.
I haven't re-checked searchback in Newburyport, so it's possible there's a new issue. What synth are you using, and how consistent is the problem? Do you still have X3 available so you can see if there's a difference with this particular project?
At the risk of re-opening a can of worms, here's a link to a summarizing post near the end of that earlier thread:
http://forum.cakewalk.com/FindPost/3336197 There's a lot of noise in the thread, so you need to read carefully to follow it from the start.