diff --git a/addons/ui/fnc_openItemContextMenu.sqf b/addons/ui/fnc_openItemContextMenu.sqf
index 3fd9328bd..5a49c1047 100644
--- a/addons/ui/fnc_openItemContextMenu.sqf
+++ b/addons/ui/fnc_openItemContextMenu.sqf
@@ -48,6 +48,10 @@ if (_options isEqualTo []) exitWith {};
 // ctrlSetBackgroundColor command does not seem to work for RscListBox.
 private _list = _display ctrlCreate [QGVAR(ItemContextMenu), -1];
 
+private _font = getText (configfile >> QGVAR(ItemContextMenu) >> "font");
+private _fontSize = getNumber (configFile >> ctrlClassName _list >> "sizeEx");
+private _longestName = "";
+
 // ---
 // Populate context menu with options.
 {
@@ -63,6 +67,10 @@ private _list = _display ctrlCreate [QGVAR(ItemContextMenu), -1];
     };
 
     if ((_slot in _slots || {"ALL" in _slots}) && {_args call _conditionShow}) then {
+        if (count _longestName < count _displayName) then {
+            _longestName = _displayName;
+        };
+
         private _index = _list lbAdd _displayName;
         _list lbSetTooltip [_index, "_tooltip"]; // Does not seem to work for RscDisplayInventory controls? Hard coded overwrite?
 
@@ -154,8 +162,8 @@ getMousePosition params ["_left", "_top"];
 _left = _left - pixelW;
 _top = _top - pixelH;
 
-private _width = ctrlPosition _list select 2;
-private _height = lbSize _list * getNumber (configFile >> ctrlClassName _list >> "sizeEx");
+private _width = (ctrlPosition _list select 2) max ((_longestName getTextWidth [_font, _fontSize]) + TEXT_MARGINS_WIDTH + RSCLISTBOX_PICTURE_WIDTH);
+private _height = lbSize _list * _fontSize;
 
 _list ctrlSetPosition [_left, _top, _width, _height];
 _list ctrlCommit 0;
diff --git a/addons/ui/script_component.hpp b/addons/ui/script_component.hpp
index 06e9a446a..431bfc06a 100644
--- a/addons/ui/script_component.hpp
+++ b/addons/ui/script_component.hpp
@@ -36,6 +36,9 @@
 #define GRID_3DEN_W (pixelW * pixelGrid * 0.5)
 #define GRID_3DEN_H (pixelH * pixelGrid * 0.5)
 
+#define TEXT_MARGINS_WIDTH (2 * 0.008)  // Hardcoded value, see https://community.bistudio.com/wiki/getTextWidth
+#define RSCLISTBOX_PICTURE_WIDTH 0.05  // Empirical value, RSCListBox's left icon picture width
+
 // Lobby Manager
 #define IDC_LM_SLOTS 50
 #define IDC_LM_CALLSIGN 51