Looks like not. After 17 Apr 2009, if parent born outside of Canada but naturalized Canadian citizen and child born outside of Canada one of parents being Canadian citizen (born outside of Canada) - Child is not Automatically Canadian citizen. Parent has to be Canadian born in Canada since 17 Apr 2009
I might be wrong... please double check.
has anyone been in this situation?
I think this is wrong but I'm going to be clear about the categories of citizenship because I'm not at all sure what you meant:
-Citizen by birth >> born in Canada >> children born abroad of this parent are citizens.
-Citizen by naturalization >> citizenship acquired by naturalization >> children born abroad of this parent are citizens IF they are born after date of naturalization.
-Citizen by descent >> citizen by right of being born abroad of Canadian citizen-parent >> children born abroad of this parent are NOT eligible for citizenship by descent. (Obviously they could be eligible via the other parent).
Note, I've only said 'parent' as it currently does not matter which parent, nor what the citizenship or residency status is of the other parent (except obviously if the other parent is a citizen and what type).