diff --git a/frontend/ui/network/manager.lua b/frontend/ui/network/manager.lua
index 5185d6b75..1bf4c68c2 100644
--- a/frontend/ui/network/manager.lua
+++ b/frontend/ui/network/manager.lua
@@ -5,6 +5,7 @@ local Device = require("device")
 local Event = require("ui/event")
 local InfoMessage = require("ui/widget/infomessage")
 local LuaSettings = require("luasettings")
+local MultiConfirmBox = require("ui/widget/multiconfirmbox")
 local UIManager = require("ui/uimanager")
 local ffiutil = require("ffi/util")
 local logger = require("logger")
@@ -135,6 +136,24 @@ function NetworkMgr:promptWifiOff(complete_callback)
     })
 end
 
+function NetworkMgr:promptWifi(complete_callback)
+    UIManager:show(MultiConfirmBox:new{
+        text = _("Wi-Fi is enabled, but you're currently not connected to a network.\nHow would you like to proceed?"),
+        choice1_text = _("Turn Wi-Fi off"),
+        choice1_callback = function()
+            self.wifi_was_on = false
+            G_reader_settings:saveSetting("wifi_was_on", false)
+            self:turnOffWifi(complete_callback)
+        end,
+        choice2_text = _("Connect"),
+        choice2_callback = function()
+            self.wifi_was_on = true
+            G_reader_settings:saveSetting("wifi_was_on", true)
+            self:turnOnWifi(complete_callback)
+        end,
+    })
+end
+
 function NetworkMgr:turnOnWifiAndWaitForConnection(callback)
     local info = InfoMessage:new{ text = _("Connecting to Wi-Fi…") }
     UIManager:show(info)
@@ -335,13 +354,15 @@ function NetworkMgr:getWifiToggleMenuTable()
         enabled_func = function() return Device:hasWifiToggle() end,
         checked_func = function() return NetworkMgr:isWifiOn() end,
         callback = function(touchmenu_instance)
-            local wifi_status = NetworkMgr:isWifiOn() and NetworkMgr:isConnected()
+            local is_wifi_on = NetworkMgr:isWifiOn()
+            local is_connected = NetworkMgr:isConnected()
+            local fully_connected = is_wifi_on and is_connected
             local complete_callback = function()
-                -- notify touch menu to update item check state
+                -- Notify TouchMenu to update item check state
                 touchmenu_instance:updateItems()
-                -- if wifi was on, this callback will only be executed when the network has been
-                -- disconnected.
-                if wifi_status then
+                -- If Wi-Fi was on when the menu was shown, this means the tap meant to turn the Wi-Fi *off*,
+                -- as such, this callback will only be executed *after* the network has been disconnected.
+                if fully_connected then
                     UIManager:broadcastEvent(Event:new("NetworkDisconnected"))
                 else
                     -- On hasWifiManager devices that play with kernel modules directly,
@@ -351,6 +372,9 @@ function NetworkMgr:getWifiToggleMenuTable()
                             UIManager:broadcastEvent(Event:new("NetworkConnected"))
                         elseif NetworkMgr:isWifiOn() and not NetworkMgr:isConnected() then
                             -- Don't leave Wi-Fi in an inconsistent state if the connection failed.
+                            -- NOTE: Keep in mind that NetworkSetting only runs this callback on *successful* connections!
+                            --       (It's called connect_callback there).
+                            --       This makes this branch somewhat hard to reach, which is why it gets a dedicated prompt below...
                             self.wifi_was_on = false
                             G_reader_settings:saveSetting("wifi_was_on", false)
                             -- NOTE: We're limiting this to only a few platforms, as it might be actually harmful on some devices.
@@ -372,8 +396,10 @@ function NetworkMgr:getWifiToggleMenuTable()
                     end
                 end
             end
-            if wifi_status then
+            if fully_connected then
                 NetworkMgr:promptWifiOff(complete_callback)
+            elseif is_wifi_on and not is_connected then
+                NetworkMgr:promptWifi(complete_callback)
             else
                 NetworkMgr:promptWifiOn(complete_callback)
             end
@@ -574,6 +600,8 @@ function NetworkMgr:showNetworkMenu(complete_callback)
                 return
             end
         end
+        -- NOTE: Also supports a disconnect_callback, should we use it for something?
+        --       Tearing down Wi-Fi completely when tapping "disconnect" would feel a bit harsh, though...
         UIManager:show(require("ui/widget/networksetting"):new{
             network_list = network_list,
             connect_callback = complete_callback,
diff --git a/frontend/ui/widget/networksetting.lua b/frontend/ui/widget/networksetting.lua
index b150c53a9..94eb69405 100644
--- a/frontend/ui/widget/networksetting.lua
+++ b/frontend/ui/widget/networksetting.lua
@@ -237,6 +237,7 @@ function NetworkItem:connect()
     end
 
     -- Do what it says on the tin, and only trigger the connect_callback on a *successful* connect.
+    -- NOTE: This callback comes from NetworkManager, where it's named complete_callback.
     if success and self.setting_ui.connect_callback then
         self.setting_ui.connect_callback()
     end