diff --git a/__pycache__/monop_players.cpython-310.pyc b/__pycache__/monop_players.cpython-310.pyc
index c403b2e..1933d65 100644
Binary files a/__pycache__/monop_players.cpython-310.pyc and b/__pycache__/monop_players.cpython-310.pyc differ
diff --git a/__pycache__/test_players.cpython-310.pyc b/__pycache__/test_players.cpython-310.pyc
new file mode 100644
index 0000000..bc86aa2
Binary files /dev/null and b/__pycache__/test_players.cpython-310.pyc differ
diff --git a/monop_players.py b/monop_players.py
index 825b488..2de5acc 100644
--- a/monop_players.py
+++ b/monop_players.py
@@ -224,16 +224,8 @@ class PlayerBot:
 
             if self.is_my_turn():
                 self.turns_played += 1
-                # ~10% chance to initiate a trade (after turn 5, not in debt)
-                if (self.turns_played > 5 and not self.in_debt
-                        and random.random() < 0.10):
-                    self.in_trade = True
-                    self.trade_props_offered = 0
-                    self.log("Initiating a trade!")
-                    self.say_delayed("trade")
-                else:
-                    self.say_delayed("roll")
-                    self.rolled_this_turn = True
+                # Trade decision is deferred to -- Command: handler
+                # to avoid race conditions with delayed messages
             return
 
         # ============================================================
@@ -444,13 +436,22 @@ class PlayerBot:
         # COMMAND PROMPT
         # ============================================================
         if msg == "-- Command:":
-            self.in_trade = False  # trade ended (accepted, rejected, or cancelled)
+            self.in_trade = False  # any active trade is over
             if self.is_my_turn():
                 if self.in_debt:
                     self.say_delayed("mortgage")
                 elif not self.rolled_this_turn:
-                    self.say_delayed("roll")
-                    self.rolled_this_turn = True
+                    # ~10% chance to initiate a trade (after turn 5, not in debt/jail)
+                    if (self.turns_played > 5 and not self.in_debt
+                            and not self.in_jail
+                            and random.random() < 0.10):
+                        self.in_trade = True
+                        self.trade_props_offered = 0
+                        self.log("Initiating a trade!")
+                        self.say_delayed("trade")
+                    else:
+                        self.say_delayed("roll")
+                        self.rolled_this_turn = True
                 # else: already rolled, waiting for prompts to resolve
             return
 
diff --git a/site/game-state.json b/site/game-state.json
index cd5904f..1d38170 100644
--- a/site/game-state.json
+++ b/site/game-state.json
@@ -1,21 +1,11 @@
 {
   "players": [
-    {
-      "name": "charlie",
-      "number": 3,
-      "money": 985,
-      "location": 40,
-      "inJail": true,
-      "jailTurns": 1,
-      "doublesCount": 0,
-      "getOutOfJailFreeCards": 0
-    },
     {
       "name": "alice",
       "number": 1,
-      "money": 1375,
-      "location": 40,
-      "inJail": true,
+      "money": 1280,
+      "location": 21,
+      "inJail": false,
       "jailTurns": 0,
       "doublesCount": 0,
       "getOutOfJailFreeCards": 0
@@ -23,8 +13,18 @@
     {
       "name": "bob",
       "number": 2,
-      "money": 800,
-      "location": 31,
+      "money": 1305,
+      "location": 16,
+      "inJail": false,
+      "jailTurns": 0,
+      "doublesCount": 0,
+      "getOutOfJailFreeCards": 0
+    },
+    {
+      "name": "charlie",
+      "number": 3,
+      "money": 1260,
+      "location": 13,
       "inJail": false,
       "jailTurns": 0,
       "doublesCount": 0,
@@ -81,7 +81,7 @@
       "id": 6,
       "name": "Oriental ave. (L)",
       "type": "property",
-      "owner": 2,
+      "owner": 3,
       "mortgaged": false,
       "group": "lightblue",
       "cost": 100,
@@ -96,7 +96,7 @@
       "id": 8,
       "name": "Vermont ave. (L)",
       "type": "property",
-      "owner": 1,
+      "owner": null,
       "mortgaged": false,
       "group": "lightblue",
       "cost": 100,
@@ -121,7 +121,7 @@
       "id": 11,
       "name": "St. Charles pl. (V)",
       "type": "property",
-      "owner": 3,
+      "owner": null,
       "mortgaged": false,
       "group": "violet",
       "cost": 140,
@@ -131,7 +131,7 @@
       "id": 12,
       "name": "Electric Co.",
       "type": "utility",
-      "owner": 2,
+      "owner": null,
       "mortgaged": false,
       "group": "utility",
       "cost": 150
@@ -140,7 +140,7 @@
       "id": 13,
       "name": "States ave. (V)",
       "type": "property",
-      "owner": null,
+      "owner": 3,
       "mortgaged": false,
       "group": "violet",
       "cost": 140,
@@ -169,7 +169,7 @@
       "id": 16,
       "name": "St. James pl. (O)",
       "type": "property",
-      "owner": null,
+      "owner": 2,
       "mortgaged": false,
       "group": "orange",
       "cost": 180,
@@ -194,7 +194,7 @@
       "id": 19,
       "name": "New York ave. (O)",
       "type": "property",
-      "owner": 3,
+      "owner": null,
       "mortgaged": false,
       "group": "orange",
       "cost": 200,
@@ -209,7 +209,7 @@
       "id": 21,
       "name": "Kentucky ave. (R)",
       "type": "property",
-      "owner": null,
+      "owner": 1,
       "mortgaged": false,
       "group": "red",
       "cost": 220,
@@ -244,7 +244,7 @@
       "id": 25,
       "name": "B&O RR",
       "type": "railroad",
-      "owner": 3,
+      "owner": null,
       "mortgaged": false,
       "group": "railroad",
       "cost": 200
@@ -273,7 +273,7 @@
       "id": 28,
       "name": "Water Works",
       "type": "utility",
-      "owner": 2,
+      "owner": null,
       "mortgaged": false,
       "group": "utility",
       "cost": 150
@@ -297,7 +297,7 @@
       "id": 31,
       "name": "Pacific ave. (G)",
       "type": "property",
-      "owner": 2,
+      "owner": null,
       "mortgaged": false,
       "group": "green",
       "cost": 300,
@@ -370,153 +370,99 @@
   ],
   "log": [
     {
-      "text": "Landed on Community Chest ii",
+      "text": "roll is 4, 6",
       "player": "alice",
-      "timestamp": "2026-02-21 10:41:53"
+      "timestamp": "2026-02-21 10:55:12"
     },
     {
-      "text": "You are Assessed for street repairs.",
-      "player": "alice"
+      "text": "Landed on Just Visiting",
+      "player": "alice",
+      "timestamp": "2026-02-21 10:55:13"
     },
     {
-      "text": "bob's turn \u2014 $1400 on Oriental ave. (L)",
+      "text": "bob's turn \u2014 $1500 on === GO ===",
       "player": "bob",
-      "timestamp": "2026-02-21 10:41:57"
+      "timestamp": "2026-02-21 10:55:14"
     },
     {
-      "text": "roll is 1, 5",
+      "text": "roll is 5, 2",
       "player": "bob",
-      "timestamp": "2026-02-21 10:41:58"
+      "timestamp": "2026-02-21 10:55:15"
     },
     {
-      "text": "Landed on Electric Co.",
+      "text": "Landed on Chance i",
       "player": "bob",
-      "timestamp": "2026-02-21 10:41:58"
+      "timestamp": "2026-02-21 10:55:15"
     },
     {
-      "text": "charlie's turn \u2014 $1160 on New York ave. (O)",
+      "text": "Pay Poor Tax of $15",
+      "player": "bob"
+    },
+    {
+      "text": "charlie's turn \u2014 $1500 on === GO ===",
       "player": "charlie",
-      "timestamp": "2026-02-21 10:42:00"
+      "timestamp": "2026-02-21 10:55:17"
     },
     {
       "text": "roll is 3, 3",
       "player": "charlie",
-      "timestamp": "2026-02-21 10:42:01"
+      "timestamp": "2026-02-21 10:55:19"
     },
     {
-      "text": "Landed on B&O RR",
+      "text": "Landed on Oriental ave. (L)",
       "player": "charlie",
-      "timestamp": "2026-02-21 10:42:01"
+      "timestamp": "2026-02-21 10:55:19"
     },
     {
-      "text": "charlie's turn \u2014 $960 on B&O RR",
+      "text": "charlie's turn \u2014 $1400 on Oriental ave. (L)",
       "player": "charlie",
-      "timestamp": "2026-02-21 10:42:04"
+      "timestamp": "2026-02-21 10:55:22"
     },
     {
-      "text": "roll is 4, 1",
+      "text": "roll is 1, 6",
       "player": "charlie",
-      "timestamp": "2026-02-21 10:42:05"
+      "timestamp": "2026-02-21 10:55:23"
     },
     {
-      "text": "Landed on GO TO JAIL!",
+      "text": "Landed on States ave. (V)",
       "player": "charlie",
-      "timestamp": "2026-02-21 10:42:05"
+      "timestamp": "2026-02-21 10:55:23"
     },
     {
-      "text": "alice's turn \u2014 $1400 on Community Chest ii",
+      "text": "alice's turn \u2014 $1500 on Just Visiting",
       "player": "alice",
-      "timestamp": "2026-02-21 10:42:06"
+      "timestamp": "2026-02-21 10:55:25"
     },
     {
-      "text": "roll is 6, 2",
+      "text": "roll is 5, 6",
       "player": "alice",
-      "timestamp": "2026-02-21 10:42:07"
+      "timestamp": "2026-02-21 10:55:26"
     },
     {
-      "text": "Landed on B&O RR",
+      "text": "Landed on Kentucky ave. (R)",
       "player": "alice",
-      "timestamp": "2026-02-21 10:42:08"
+      "timestamp": "2026-02-21 10:55:27"
     },
     {
-      "text": "Paid $25 rent to charlie",
-      "player": "alice"
-    },
-    {
-      "text": "bob's turn \u2014 $1250 on Electric Co.",
+      "text": "bob's turn \u2014 $1485 on Chance i",
       "player": "bob",
-      "timestamp": "2026-02-21 10:42:09"
+      "timestamp": "2026-02-21 10:55:29"
     },
     {
-      "text": "roll is 4, 4",
+      "text": "roll is 3, 6",
       "player": "bob",
-      "timestamp": "2026-02-21 10:42:10"
+      "timestamp": "2026-02-21 10:55:30"
     },
     {
-      "text": "Landed on Free Parking",
+      "text": "Landed on St. James pl. (O)",
       "player": "bob",
-      "timestamp": "2026-02-21 10:42:11"
+      "timestamp": "2026-02-21 10:55:30"
     },
     {
-      "text": "bob's turn \u2014 $1250 on Free Parking",
-      "player": "bob",
-      "timestamp": "2026-02-21 10:42:12"
-    },
-    {
-      "text": "roll is 6, 2",
-      "player": "bob",
-      "timestamp": "2026-02-21 10:42:13"
-    },
-    {
-      "text": "Landed on Water Works",
-      "player": "bob",
-      "timestamp": "2026-02-21 10:42:14"
-    },
-    {
-      "text": "charlie's turn \u2014 $985 on JAIL",
+      "text": "charlie's turn \u2014 $1260 on States ave. (V)",
       "player": "charlie",
-      "timestamp": "2026-02-21 10:42:16"
-    },
-    {
-      "text": "roll is 6, 5",
-      "player": "charlie",
-      "timestamp": "2026-02-21 10:42:17"
-    },
-    {
-      "text": "alice's turn \u2014 $1375 on B&O RR",
-      "player": "alice",
-      "timestamp": "2026-02-21 10:42:18"
-    },
-    {
-      "text": "roll is 2, 3",
-      "player": "alice",
-      "timestamp": "2026-02-21 10:42:20"
-    },
-    {
-      "text": "Landed on GO TO JAIL!",
-      "player": "alice",
-      "timestamp": "2026-02-21 10:42:20"
-    },
-    {
-      "text": "bob's turn \u2014 $1100 on Water Works",
-      "player": "bob",
-      "timestamp": "2026-02-21 10:42:21"
-    },
-    {
-      "text": "roll is 1, 2",
-      "player": "bob",
-      "timestamp": "2026-02-21 10:42:22"
-    },
-    {
-      "text": "Landed on Pacific ave. (G)",
-      "player": "bob",
-      "timestamp": "2026-02-21 10:42:22"
-    },
-    {
-      "text": "charlie's turn \u2014 $985 on JAIL",
-      "player": "charlie",
-      "timestamp": "2026-02-21 10:42:24"
+      "timestamp": "2026-02-21 10:55:32"
     }
   ],
-  "lastUpdated": "2026-02-21T10:42:27.015680+00:00"
+  "lastUpdated": "2026-02-21T10:55:32.750315+00:00"
 }
\ No newline at end of file
diff --git a/test_players.py b/test_players.py
index 63fde51..7cfc8aa 100644
--- a/test_players.py
+++ b/test_players.py
@@ -115,8 +115,13 @@ class TestTurns(unittest.TestCase):
         return bot
 
     def test_checkpoint_triggers_roll(self):
+        """Checkpoint sets up turn, -- Command: triggers the roll."""
         bot = self._make_bot("alice")
         msgs = bot.feed("alice (1) (cash $1500) on === GO ===")
+        self.assertEqual(msgs, [], "Checkpoint should not send commands")
+        # Roll happens at -- Command:
+        with patch("random.random", return_value=0.99):  # no trade
+            msgs = bot.feed("-- Command:")
         self.assertIn("roll", msgs)
         self.assertTrue(bot.rolled_this_turn)
 
@@ -224,11 +229,12 @@ class TestTrading(unittest.TestCase):
 
     @patch("monop_players.random")
     def test_trade_initiated(self, mock_random):
-        """With random < 0.10, bot initiates trade instead of rolling."""
+        """With random < 0.10, bot initiates trade at -- Command:."""
         mock_random.random.return_value = 0.05  # < 0.10
         bot = self._make_bot("alice")
         bot.turns_played = 10  # past turn 5
-        msgs = bot.feed("alice (1) (cash $1500) on === GO ===")
+        bot.feed("alice (1) (cash $1500) on === GO ===")
+        msgs = bot.feed("-- Command:")
         self.assertIn("trade", msgs)
         self.assertTrue(bot.in_trade)
         self.assertNotIn("roll", msgs)
@@ -239,7 +245,8 @@ class TestTrading(unittest.TestCase):
         mock_random.random.return_value = 0.05
         bot = self._make_bot("alice")
         bot.turns_played = 2
-        msgs = bot.feed("alice (1) (cash $1500) on === GO ===")
+        bot.feed("alice (1) (cash $1500) on === GO ===")
+        msgs = bot.feed("-- Command:")
         self.assertIn("roll", msgs)
         self.assertFalse(bot.in_trade)
 
@@ -332,21 +339,18 @@ class TestTradeInJail(unittest.TestCase):
         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."""
+    def test_no_trade_from_jail(self):
+        """Can't trade while in jail — must roll first."""
         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("charlie (3) (cash $985) on JAIL")
         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")
+        self.assertIn("roll", msgs, "Should roll in jail")
+
+        # Even if random triggers, no trade while in_jail
+        with patch("random.random", return_value=0.01):
+            msgs = bot.feed("-- Command:")
+        self.assertFalse(bot.in_trade, "Should not trade while in jail")
+        self.assertIn("roll", msgs)
 
     def test_trade_which_player_prompt(self):
         """Bot should pick a trade partner when asked."""
@@ -371,16 +375,31 @@ class TestTradeInJail(unittest.TestCase):
         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."""
+    def test_trade_done_triggers_roll(self):
+        """Trade is done! resets in_trade and triggers roll."""
         bot = self._make_bot()
         bot.current_player = "charlie"
         bot.in_trade = True
         bot.rolled_this_turn = False
-        msgs = bot.feed("-- Command:")
+        msgs = bot.feed("Trade is done!")
         self.assertFalse(bot.in_trade)
         self.assertIn("roll", msgs)
 
+    def test_trade_decision_at_command_prompt(self):
+        """Trade/roll decision happens at -- Command:, not at checkpoint."""
+        bot = self._make_bot()
+        # Checkpoint just records the turn
+        msgs = bot.feed("charlie (3) (cash $1500) on === GO ===")
+        self.assertNotIn("trade", msgs, "Checkpoint must not send trade")
+        self.assertNotIn("roll", msgs, "Checkpoint must not send roll")
+
+        # -- Command: is where the decision happens
+        with patch("random.random", return_value=0.01):  # triggers trade
+            msgs = bot.feed("-- Command:")
+        self.assertTrue(bot.in_trade)
+        self.assertIn("trade", msgs)
+        self.assertNotIn("roll", msgs)
+
 
 class TestValidInputs(unittest.TestCase):
     def test_picks_first_option(self):