It looks like that never occurs for Helvetica (A316600) due to the absence of kerning. However, with Arial (A316599) the description notes:
> a(29368) = 111111 is a first notable anomaly, because its bounding box width of 2675 lies between those of a(29367) = 49115, with bounding box width 2655, and a(29369) = 70002, with bounding box width 2681.
Any OEIS post is interesting and worthy of HN. Sometimes Numberphile videos even come out the other end with extremely interesting animations of the results. This latest video was very good:
https://oeis.org/history?seq=A133451&start=0&n=30