This post is similar to mine at Monthly timeline view missing for recent months - #5 by matt
I’m on 3.4.4 also and leaving it running doesn’t seem to be achieving anything. My monthly views still stop in mid-February (I can tell that February is incomplete from missing locations). I’m fastidious about maintaining my logs so I’m pretty sure I’ll have minimal ‘transport’ type trips. Certainly I have no days highlighted in grey on my calendar for February…