Debounce not working?

Hierarchy:

- Tool
    - Script
    - LocalScript
    - RemoteEvent

Server Script:

local tool      = script.Parent
local lib       = require(game.ServerStorage.Library)
local detain    = tool:WaitForChild("Detain")
local detained  = {}
local detainedChar
local connections = {}

local function removeTools(chr)
    for _,obj in next, chr:GetChildren() do
        if obj:IsA("Tool") or obj:IsA("HopperBin") then
            wait()
            obj.Parent  = game.Players:GetPlayerFromCharacter(chr).Backpack
        end
    end
end

local function setCanCollide(chr, bool)
    for _,obj in next, chr:GetChildren() do
        if obj:IsA("BasePart") then
            obj.CanCollide = bool
            print(obj.Name.." is now set CanCollide to "..tostring(bool))
        end
        setCanCollide(obj, bool)
    end
end

detain.OnServerEvent:connect(function(plr, type, detainee, code)
    if code ~= "PQ8pYaSCNp" then print("Wrong code, "..detainee.Name..". Try again next time.") return end
    local hum   = lib.GetHumanoid(detainee)
    if type == "Detain" then
        print(detained[detainee]) -- this prints nothing!
        if detained[detainee] then print(plr.Name.." tried to detain "..detainee.Name.." but he/she was already detained.") return end -- this doesn't print when someone is detained, and someone else tries to detain them!
        print("Detaining "..detainee.Name)
        detained[detainee] = true
        spawn(function() for i,v in next, detained do
            print(tostring(i).." is detained.")
        end end)
        setCanCollide(detainee, false)
        detainee.Torso.Anchored = true
        hum.JumpPower   = 0
        hum.WalkSpeed   = 0
        connections[1]  = detainee.ChildAdded:connect(function()
            removeTools(detainee)
        end)
        connections[2]  = lib.GetHumanoid(plr.Character).Died:connect(function()
            detained[detainee] = false
        end)
        removeTools(detainee)
        spawn(function()
            while detained[detainee] do
                wait()
                detainee:SetPrimaryPartCFrame(plr.Character:GetPrimaryPartCFrame() * CFrame.new(0, 0, -2.5))
            end
        end)
        detain:FireClient(plr, true)
    elseif type == "Undetain" then
        print("Undetaining "..detainee.Name)
        detainee.Torso.Anchored = false
        hum.JumpPower   = 50
        hum.WalkSpeed   = 16
        setCanCollide(detainee, true)
        detained[detainee] = false
        for i,v in next, connections do v:disconnect() end
        detain:FireClient(plr, false)
    end
end)

LocalScript:

local plr           = game.Players.LocalPlayer
local m             = plr:GetMouse()
local chr           = plr.Character or plr.CharacterAdded:wait()
local tool          = script.Parent
local detain        = tool:WaitForChild("Detain")
local    code           = "PQ8pYaSCNp"
local detainee  = false
local last

tool.Activated:connect(function()
    if not detainee then
        local detained = game.Players:GetPlayerFromCharacter(m.Target.Parent).Character -- just to make sure it's an actual player, k?
        if detained then
            detain:FireServer("Detain", detained, code)
        end
        last = detained
    elseif detainee then
        detainee    = false
        detain:FireServer("Undetain", last, code)
    end
end)

detain.OnClientEvent:connect(function(bool)
    detainee = bool
end)

This script is suppose to only allow one person to detain a specified player at a time.

Okay, so my problem is that "detained[detainee]" is never set to true (I think?), because when someone is detained and someone else tries to detain them, it never prints "Player tried to detain Player1, but Player1 was already detained".

Anyone know why this debounce isn't working? Probably a stupid question, but I need help.

Most of the problems are on lines 31, and 32.