I believe Air Canada owes your colleague a free hotel room, Meal Vouchers, Denied Boarding Compensation to take the later flight and transportation to and from the hotel as well. It was beyond your colleague's control about the boarding pass link but if it were me I would not wait until 45 minutes to clear security especially on a flight to Canada where they close the flight earlier for Customs and security purposes!
A reprint of a boarding pass should have been done as the passenger was checked in. Was the passport verified by a ticket counter agent? This is the only reason that the link was not working because if the reservation said"See Agent or tis is not a boarding pass".