Originally Posted by zwkchong

Your chances of making the connection are very slim, even if you have no delays. If you don't get your 2nd boarding pass at HAV (keep in mind this is an outstation in Cuba), you would have less than 30 minutes to run from your arrival gate to immigration, clear entry immigration and run to your check in counter.

If you do get a boarding pass at HAV, it MAY be possible but keep in mind as it's two separate bookings, you will be at the mercy of Air Canada if you miss your connection.