eUpgrade request across multiple flights with different request windows
 

I have previously eUpgraded only on direct international flights without connections or with multiple segments with same the flight number (AC 33/34), but I always believed that a single eUpgrade covered all segments on a single trip — in this case, YYZ-YVR-MEL — although the AC webpages on eUpgrades are less than explicit on this point. However, I'm uncertain how I should approach the eUpgrade request when the segments have different request windows (see screenshot). Should I just wait until 7 days? Should I request the YYZ-YVR segment at 14 days, and then try to somehow add YVR-MEL at 7 days? I don't want to get charged upgrade points separately for each segment.

Have no fear, the full sum won't be charged in the end and it will correct itself and charge you the YYZ MEL distance. So just upgrade at the window for each flight as necessary.