For AC's mainline fleet it is 100% automated now that the DC9's have been retired. They all work from an Air-to-Ground datalink.
The times recorded are out/off/descent through 10,000feet/on/in. The times are compared against the calculated flight plan and downline estimates are made at each point. The flight crew may also initiate a "position report" which generates messages to the company and adjusts the ETA.
The FIDS screens at the airports and on the Internet are generally integrated into receiving these messages automatically also.
The other systems from the Internet such as Flight Tracker receive all of their information from the FAA ATC system [and they are delayed by about 20 minutes for security reasons]

Internal to the company any delay over 5 minutes needs accountability so whether it was 25mins late or 40mins would make little difference. The change had to be effected by the System Operations Control Centre in YYZ and they do not make these adjustments without good reason, especially if it meens the crew would get an additional 40 minutes pay.