diff --git a/common/script/index.js b/common/script/index.js
index d82a39f04a..ee3790af6f 100644
--- a/common/script/index.js
+++ b/common/script/index.js
@@ -1392,9 +1392,9 @@ api.wrap = function(user, main) {
         } else {
           if (user.preferences.autoEquip) {
             user.items.gear.equipped[item.type] = item.key;
+            message = user.fns.handleTwoHanded(item, null, req);
           }
           user.items.gear.owned[item.key] = true;
-          message = user.fns.handleTwoHanded(item, null, req);
           if (message == null) {
             message = i18n.t('messageBought', {
               itemText: item.text(req.language)
diff --git a/test/common/user.fns.buy.test.js b/test/common/user.fns.buy.test.js
index e04c395533..a4b067f9f4 100644
--- a/test/common/user.fns.buy.test.js
+++ b/test/common/user.fns.buy.test.js
@@ -101,6 +101,34 @@ describe('user.fns.buy', () => {
       expect(user.items.gear.equipped).to.not.have.property('armor');
     });
 
+    it('removes one-handed weapon and shield if auto-equip is on and a two-hander is bought', () => {
+      user.stats.gp = 100;
+      user.preferences.autoEquip = true;
+      user.ops.buy({params: {key: 'shield_warrior_1'}});
+      user.ops.equip({params: {key: 'shield_warrior_1'}});
+      user.ops.buy({params: {key: 'weapon_warrior_1'}});
+      user.ops.equip({params: {key: 'weapon_warrior_1'}});
+
+      user.ops.buy({params: {key: 'weapon_wizard_1'}});
+
+      expect(user.items.gear.equipped).to.have.property('shield', 'shield_base_0');
+      expect(user.items.gear.equipped).to.have.property('weapon', 'weapon_wizard_1');
+    });
+
+    it('buys two-handed equipment but does not automatically remove sword or shield', () => {
+      user.stats.gp = 100;
+      user.preferences.autoEquip = false;
+      user.ops.buy({params: {key: 'shield_warrior_1'}});
+      user.ops.equip({params: {key: 'shield_warrior_1'}});
+      user.ops.buy({params: {key: 'weapon_warrior_1'}});
+      user.ops.equip({params: {key: 'weapon_warrior_1'}});
+
+      user.ops.buy({params: {key: 'weapon_wizard_1'}});
+
+      expect(user.items.gear.equipped).to.have.property('shield', 'shield_warrior_1');
+      expect(user.items.gear.equipped).to.have.property('weapon', 'weapon_warrior_1');
+    });
+
     it('does not buy equipment without enough Gold', () => {
       user.stats.gp = 20;