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So I found myself in this situation:

My characters are in a land composed mainly of city states with some degree of recognition of common nationality (a la greeks at the time of the persian wars), the land has been conquered by the empire that is its northern neighbor, with the exception of one of the largest cities, which is besieged.

They have formed a small rebellion force (cliche, I know) and gotten a lucky victory, now an imperial army has marched into the land and is a few days' march away from their much smaller, untrained, less well-equipped force.

The land has plenty of dense forests and rich fields for them to hide in and eat from, as well as a few large mountain ridges. The population should for the most part be on the rebels' side. I am having a hard time figuring out several things. I realise they should employ some form of guerilla warfare but I dont understand how an army that is untrained, unequipped, and not reliably supplied food or water can do so, against a force that is all these things.

I hope this is question is fine, thanks in advance.

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    $\begingroup$ Welcome to worldbuilding, please one worldbuilding question per post. Take a read at our help center for more info $\endgroup$ – L.Dutch May 21 at 10:43
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    $\begingroup$ Rebel movements don't focus on body count, they make the occupation no longer worth it. Usually this means targeting something that is vital to the local economy but difficult to defend. Why does the empire want the land? Destroy the thing they want to extract, or make it more trouble than it's worth. Or manipulate regional politics so that your home is no longer a strategic location worth holding. $\endgroup$ – user72058 May 21 at 11:23
  • $\begingroup$ I mean, not all guerillas are composed of highly trained, well experienced soldiers, in fact, many guerrillas are precisely groups of people with smaller numbers and less gear trying to make sure they engage as little as possible and that the battles they do fight are on their terms and in ground they dominate. The guerrillas in Vietnam also had a fairly large number of untrained rice farmers. $\endgroup$ – ProjectApex May 21 at 12:14
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    $\begingroup$ In a straight-up battle, the rebel force will not just be defeated but obliterated. The rebels must play as dirty as they can: disrupt supply lines and steal supplies, ambush scouting and foraging parties, take advantage of their knowledge of local terrain to lay traps and ambushes, force the opponent to spread their forces thin by using pinprick attacks over areas the imperial forces have occupied, buy time to train and recruit, etc. Even then, if the occupiers are willing to be brutal enough by terrorizing or even simply eliminating the local populace, they will eventually be overwhelmed. $\endgroup$ – GrumpyYoungMan May 21 at 14:08
  • $\begingroup$ This is a rare case when I agree that the question is too story-based since your entire book/game/etc. can be an answer to this question. I would suggest doing a bit more research on guerilla warfare and then asking questions targeting specific areas that you are having difficulties with, for example, armour and weapons for the rebels or supply logistics. $\endgroup$ – Otkin May 21 at 20:27
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Supply Lines

Your rebels cannot win a straight-up fight. So they won't give the enemy one!

An army in the field, especially an ancient army, cannot bring its own rations with it. It needs a continuous train of supplies, preferably by boat as grain transport via barge/ship is HUGELY more efficient than animal-pulled wagon trains. If the population is on your rebel's side, the easy answer is burn the fields, chase off the game, and have your rebel army act as a lure while whatever compromises your mobile force (preferably cavalry, but light infantry will work in a pinch if its forested/the enemy has few horsemen) attacks the enemy supply wagons. Disruption needn't take a long time. Stopping supplies for a week or two when there's no forage for the army could easily lead to serious problems resulting in the retreat/starvation of the superior force.

Potential Problems: The enemy guards the caravans too well to be attacked. If this starts to happen it may weaken the main force enough for your "plucky rebels" to win the day in a fight with what remains of the army.

The Enemy Spreads Out In an attempt to keep fed off the land, the enemy army sends out foragers in small groups in all directions. This could lead to them finding sufficient food to bring your rebels to a decisive battle they can't win. On the other hand, it can also result in your rebels ambushing and annihilating these small foraging parties, especially if the locals are happy to point them out to your rebels!

The Locals Starve Burning the crops and hiding the food is all very well, but your locals NEED that food to survive. Destroy too much, fail to hide enough from enemy foraging parties, and the locals start starving to death. Starving peasants are much more likely to sell out your rebels than ones that have enough to eat. Politics only count for so much if your kid is dying of malnutrition. Not much to get around this, ancient war is HARD on peons. But perhaps if it's a fall campaign your rebels could work out a deal with some other power/polity to bring in foodstuffs after the enemy army is driven off. You could also try to feed them of captured supplies, but that's much tougher logistically than using it to simply feed your raiders/army.

As an aside, while your army may not be reliably supplied with food, they should have adequate water if the locals are on their side. If there is so little water they're having trouble even when they know where the water is, your problem gets much simpler. Poison the wells along the enemy's advance. It's not hard, just throw a dead sheep in and it's done. An army without water dies even faster than one without food, and the enemy will be compelled to either pull back or die.

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You might to look into the Skanderbeg Rebellion against the Ottoman Empire. Skanderbeg kept the Ottomans at bay for 25 years by leading the disunited Albanians with a force that never exceeded 10000 men.

Apart from having a brilliant and lucky leader, diplomacy is the name of the game. Forge in a punitive coalition to dismantle the empire. Or become the vassal of a rival power and hope that they beat the empire with and for you. Many polities in history survived by using the great powers around them against each other. Buffer states and marches can be valuable. And when both Empires have ground each other down, the rebel nation might gain independence.

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Chekhov's gun: "If you say in the first chapter that there is a rifle hanging on the wall, in the second or third chapter it absolutely must go off."

I looked in your setup for a hint about what your rebels should do. I found it.

the land has been conquered by the empire that is its northern neighbor, with the exception of one of the largest cities, which is besieged.

There is one place that your rebels can hide from the imperial army that is closing in on them: that city. They head for it as fast as they can. When they get there, they catch the besieging army totally unprepared and proceed to handily hand them their asses. The amazed folks in the city are very pleased to let the rebels in.

The pursuing imperials encounter escapees from the formerly besieging army and arrive to find the rebels behind the wall and the city no longer under siege. Begin book 3.

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This happened several times in real history, the answer was usually better tactics and better relations with the locals.

medieval armies were rarely well trained, or well supplied. Usually relying on local procurement of food and water and untrained conscripts. An army of levy conscripts is not going to have the same moral or effectiveness as an army of committed locals defending their home. It gets even worse if the local climate and terrain is drastically different than the norm for the empire. heavy Calvary is great on open grassland and useless in the mountains or swamps. this is why conquest was often considered a feat of greatness, armies were hard to create, control, and maintain.

Being liked by the locals meant easier access to food and water. Taking them by force could work once but rarely could be sustained for long, a well liked force on the other hand might simply be given supplies. Look at the crusades for how much being liked by the locals could matter. If you loot a town you then must use troops to hold the town otherwise that town may very well cut your supply line as soon as you march away. Foolish leadership can create this problem even in your own country. A fool in leadership can create problem on your home turf that a good leader will never encounter even on enemy ground.

Better tactics could cover a host of short comings by itself. Look at Hannibal and Scipio for some great uses of tactics. Inferior forces beating larger ones was practically the theme of those wars.

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Mobility. Evasion. Disguise. Infiltration.

Definitely NOT by massing their feeble army in a set-piece battle against a superior foe. Take the fight to the hills, to the forests.

The rebels' smaller army, with likely less training and definitely less equipment and support infrastructure than the Empire, simply cannot defeat them in a stand-up battle.

But why would they need to?

They have a much more fluid organizational structure.
They can disguise themselves and blend in with civilian populations.
They can do the terrorist thing: Nasty, but effective. Poison wells. Sow caltrops on the road ahead of the marching Empire army. Send in diseased camp-folowers. Raise public sentiment against the Empire, using false-flag atrocities if they have to.

The Empire has to follow their own rules, as all their actions reflect upon their leaders. They have to follow their own organizational rules, restricting what and where and how they may act. They have to stay within the bounds of their civilization.

The Rebels do not. They are free to act as they need.

In informal war, the forces of Order will always need to use disproportionate efforts to match and counter the actions of the informal fighters.

The rebels can win when the Empire find it uneconomical to sustain this unbalanced effort to suppress the Rebels. i.e. "It's just not worth it, to fight for those dang provinces any more"

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