I have had that that problem sometimes when pressing start on the M:C, when I have live-recorded a sequence. That I understand (my timing was out, so the ‘nudge’ for the first step is negative, it was too early).
But if you’re seeing the problem only with the keystep start and not with the M:C start, that must mean something different is happening.
Yes @bibenu, I normally program beats with the step-sequencer on the model cycles without nudging the beats off the regular grid. Keystep is playing other synths but controlling synchronisation and clock.
I have the same problem with my Digitakt. Micro-timing is dead center, and when pressing play on the DT itself it always works as it should. Starting it from another device (DAW through midi, no overbridge), it skips the first beat half the times.
This is a known bug, and we’re working on fixing the problem. In the meantime, a workaround is to nudge the first trig of the track to +1/384. It should then play consistently on MIDI start.