Fix trade-in-jail bug: jail handler must not roll during active trade

Added guard in jail turn handler to skip rolling when in_trade is True.
The roll happens later when '-- Command:' arrives after trade completes.

Added 5 regression tests for the exact failing sequence.

monop_players.py

@@ -250,7 +250,8 @@ class PlayerBot:
                     self.jail_turns = 2
                 else:
                     self.jail_turns = 1
-                # Try rolling doubles
+                # Try rolling doubles — but not if we're in a trade
+                if not self.in_trade:
                     self.say_delayed("roll")
             return
 

test_players.py

@@ -306,6 +306,82 @@ class TestTrading(unittest.TestCase):
         self.assertIn("roll", msgs)
 
 
+class TestTradeInJail(unittest.TestCase):
+    """Regression tests for trade-while-in-jail bug.
+
+    Sequence that caused the hang:
+      1. Checkpoint "charlie (3) (cash $985) on JAIL" → trade initiated
+      2. "(This is your 2nd turn in JAIL)" → roll queued (ignoring in_trade)
+      3. ".trade" sent, then ".roll" sent into trade prompt → hang
+    """
+
+    def _make_bot(self, nick="charlie"):
+        bot = FakePlayerBot(nick, ["alice", "bob", "charlie"], 2)
+        bot.setup_phase = False
+        bot.game_started = True
+        bot.turns_played = 10  # past trade threshold
+        return bot
+
+    def test_jail_handler_no_roll_during_trade(self):
+        """Jail turn handler must not queue a roll when in_trade is True."""
+        bot = self._make_bot()
+        bot.current_player = "charlie"
+        bot.in_trade = True
+        bot.in_jail = True
+        msgs = bot.feed("(This is your 2nd turn in JAIL)")
+        self.assertNotIn("roll", msgs,
+                         "Should not roll while in_trade is True")
+
+    def test_trade_then_jail_turn_sequence(self):
+        """Simulate the exact sequence: checkpoint initiates trade, then jail prompt arrives."""
+        bot = self._make_bot()
+        # Force trade to trigger (patch random)
+        with patch("random.random", return_value=0.01):  # < 0.10 → triggers trade
+            msgs = bot.feed("charlie (3) (cash $985) on JAIL")
+        self.assertTrue(bot.in_trade, "Trade should be initiated")
+        self.assertIn("trade", msgs, "Should send .trade")
+        self.assertNotIn("roll", msgs, "Should not also roll")
+
+        # Now jail turn prompt arrives
+        msgs = bot.feed("(This is your 2nd turn in JAIL)")
+        self.assertNotIn("roll", msgs,
+                         "Jail handler must not roll during active trade")
+        self.assertTrue(bot.in_trade, "Trade should still be active")
+
+    def test_trade_which_player_prompt(self):
+        """Bot should pick a trade partner when asked."""
+        bot = self._make_bot()
+        bot.current_player = "charlie"
+        bot.in_trade = True
+        msgs = bot.feed("Which player do you wish to trade with?")
+        self.assertTrue(len(msgs) > 0, "Should respond to trade partner prompt")
+        self.assertNotIn("roll", msgs)
+        # Should pick one of the other players
+        self.assertTrue(
+            msgs[0] in ["alice", "bob"],
+            f"Expected a player name, got: {msgs[0]}"
+        )
+
+    def test_no_trade_in_jail_still_rolls(self):
+        """When NOT in a trade, jail handler should still queue a roll."""
+        bot = self._make_bot()
+        bot.current_player = "charlie"
+        bot.in_trade = False
+        bot.in_jail = True
+        msgs = bot.feed("(This is your 2nd turn in JAIL)")
+        self.assertIn("roll", msgs, "Should roll when not trading")
+
+    def test_command_prompt_after_trade_allows_roll(self):
+        """After trade ends (-- Command:), bot should roll normally."""
+        bot = self._make_bot()
+        bot.current_player = "charlie"
+        bot.in_trade = True
+        bot.rolled_this_turn = False
+        msgs = bot.feed("-- Command:")
+        self.assertFalse(bot.in_trade)
+        self.assertIn("roll", msgs)
+
+
 class TestValidInputs(unittest.TestCase):
     def test_picks_first_option(self):
         bot = FakePlayerBot("alice", ["alice", "bob"], 0)