With the Canadians (I am having trouble remembering their name and I don't wanna keep going back and forth to look) attempting to invade the south of Cuba via a naval invasion, we will jump into immediate action. Our navy will be reorganized based on recent activities and begin creating 'Closed Off Sea Areas' which is then split into 2 divisions. Our main naval ships like destroyers, submarines, etc are mobilized and split into fleets. One fleet will block off entrance access based on the eastern waters of the Bahamas, another focuses on the eastern/southeastern waters of Cuba, another around Jamaica (the cyan at the bottom of the map, but it looks like Cuba because that's the point of it), and southwestern waters of Cuba. Then, coastal patrols will be mobilized and organized into 'Patrol Fleets', the first one will patrol the Florida Keys and waters south of that while the other will focus on the southern coasts of Cuba. This is to begin checks on ships entering Cuba, keeping other nations' naval units away from us unless they are there to help us, and if they find Canadian weapons or soldiers trying to access Cuba, they will be detained. This brings us to the mainland of Cuba. All ports on the eastern half of the island will have military checkpoints for incoming ships and daily/nightly patrols for ships entering. Curfews will be placed in areas near the current war zone so anyone that is out passed that will be arrested. This will be broadcast throughout the entire island of Cuba as best as we can so if someone tries to say they were never informed, it's because of them being ignorant. Newspapers and soldiers will also make sure to tell locals about this if they don't have internet or are poor to make sure they know. Military units from Cuba and to an extent, Jamaica, will be sent to the east of Cuba where they will begin splitting it off from the rest of the island in terms of free movement. To deal with any guerrilla activities, we will begin using drones to our advantage and begin deploying them to monitor their movements so we can prepare for an attack or hit them on the run. Population centers, including small towns and stuff will be included in the curfews and will have some kind of a military presence to ensure that anyone entering the area will have to go through identification checks to make sure no guerrilla fighters get to enter and stage an attack or find refuge there. Finally, our military, instead of trying to battle the militants head on using conventional means, we will use different tactics. Our military will use small, flexible, elite units who will be capable of rapid tracking and immediate response to avoid relying on slower, predictable conventional troops as the main way to deal with these guys.
I have no clue if I was or was not supposed to remix @sillymink 's response lol