Can a court order an unsuccessful will challenger to personally pay the estate's legal costs?

Yes. While estate litigation has a history of courts sometimes ordering costs paid out of the estate rather than by the losing party personally, that approach is no longer automatic, and Ontario courts today will often order an unsuccessful will challenger to personally pay some or all of the estate's legal costs, just as in ordinary civil litigation, particularly where the challenge wasn't reasonably justified by the deceased's own conduct or the circumstances surrounding the will.

Courts look at factors like whether there were legitimate grounds that made investigation reasonable, how the litigation was conducted, whether reasonable settlement offers were rejected, and whether the challenge appears to have been driven by personal grievance rather than a genuine concern about the will's validity. A challenger who pursues a weak claim aggressively, ignores opportunities to resolve the matter, or conducts the litigation in a way that increases costs unnecessarily is at real risk of a substantial personal costs award, on top of losing the underlying challenge. Because the exposure can be significant, anyone considering challenging a will should get a realistic assessment of both the merits and the potential costs consequences before starting, not after the litigation is already underway.