strange behavior when toggling drawing

[Subbeh]

I've been looking at this problem for a couple of days, and I'm really starting to doubt my sanity.

The following snippet is a simplified example that uses some questionable logic that makes more sense in the full context.

I have a button, an icon and a text item. The button toggles the icon and text to be drawn and triggers a function.
The toggling of the visibility works, but the function is only triggered when drawing = false.

local enabled = true
local reset_item

local function init_bar()
	local menu_icon = sbar.add("item", "menu.icon", {
		icon = {
			string = "M",
		},
	})

	local item_icon = sbar.add("item", "menu.item.icon", {
		icon = {
			string = "I",
		},
	})

	sbar.add("item", "menu.item.text", {
		label = "TEXT",
	})

	item_icon:subscribe({ "reset_items" }, reset_item)

	menu_icon:subscribe("mouse.clicked", function()
		enabled = not enabled -- inverse the boolean
		sbar.set("/menu\\.item\\..*/", { drawing = enabled }) -- toggle the menu visibility
		print("drawing = " .. tostring(enabled)) -- debug statement showing the value of "enabled"

		sbar.trigger("reset_items") -- trigger the reset_items function (DOES NOT RUN WHEN enabled = true)
	end)
end

reset_item = function()
	print("TEST")
end

init_bar()

The output when I press the button, setting drawing = false:

drawing = false
TEST

The output when I press the button, setting drawing = true:

drawing = true

I'm expecting the output to show TEST when drawing is set back to true.