diff --git a/catanatron_core/catanatron/models/actions.py b/catanatron_core/catanatron/models/actions.py
index 9bb414dc..1657ccaa 100644
--- a/catanatron_core/catanatron/models/actions.py
+++ b/catanatron_core/catanatron/models/actions.py
@@ -51,14 +51,26 @@ def generate_playable_actions(state) -> List[Action]:
     elif action_prompt == ActionPrompt.MOVE_ROBBER:
         return robber_possibilities(state, color)
     elif action_prompt == ActionPrompt.PLAY_TURN:
+        actions = []
+        # Allow playing dev cards before and after rolling
+        if player_can_play_dev(state, color, "YEAR_OF_PLENTY"):
+            actions.extend(year_of_plenty_possibilities(color, state.resource_freqdeck))
+        if player_can_play_dev(state, color, "MONOPOLY"):
+            actions.extend(monopoly_possibilities(color))
+        if player_can_play_dev(state, color, "KNIGHT"):
+            actions.append(Action(color, ActionType.PLAY_KNIGHT_CARD, None))
+        if (
+            player_can_play_dev(state, color, "ROAD_BUILDING")
+            and len(road_building_possibilities(state, color, False)) > 0
+        ):
+            actions.append(Action(color, ActionType.PLAY_ROAD_BUILDING, None))
+
         if state.is_road_building:
             actions = road_building_possibilities(state, color, False)
         elif not player_has_rolled(state, color):
-            actions = [Action(color, ActionType.ROLL, None)]
-            if player_can_play_dev(state, color, "KNIGHT"):
-                actions.append(Action(color, ActionType.PLAY_KNIGHT_CARD, None))
+            actions.append(Action(color, ActionType.ROLL, None))
         else:
-            actions = [Action(color, ActionType.END_TURN, None)]
+            actions.append(Action(color, ActionType.END_TURN, None))
             actions.extend(road_building_possibilities(state, color))
             actions.extend(settlement_possibilities(state, color))
             actions.extend(city_possibilities(state, color))
@@ -70,21 +82,6 @@ def generate_playable_actions(state) -> List[Action]:
             if can_buy_dev_card:
                 actions.append(Action(color, ActionType.BUY_DEVELOPMENT_CARD, None))
 
-            # Play Dev Cards
-            if player_can_play_dev(state, color, "YEAR_OF_PLENTY"):
-                actions.extend(
-                    year_of_plenty_possibilities(color, state.resource_freqdeck)
-                )
-            if player_can_play_dev(state, color, "MONOPOLY"):
-                actions.extend(monopoly_possibilities(color))
-            if player_can_play_dev(state, color, "KNIGHT"):
-                actions.append(Action(color, ActionType.PLAY_KNIGHT_CARD, None))
-            if (
-                player_can_play_dev(state, color, "ROAD_BUILDING")
-                and len(road_building_possibilities(state, color, False)) > 0
-            ):
-                actions.append(Action(color, ActionType.PLAY_ROAD_BUILDING, None))
-
             # Trade
             actions.extend(maritime_trade_possibilities(state, color))
         return actions
diff --git a/catanatron_core/catanatron/state.py b/catanatron_core/catanatron/state.py
index 665eab8c..2a3c98d5 100644
--- a/catanatron_core/catanatron/state.py
+++ b/catanatron_core/catanatron/state.py
@@ -76,6 +76,10 @@
     # de-normalized features (for performance since we think they are good features)
     "ACTUAL_VICTORY_POINTS": 0,
     "LONGEST_ROAD_LENGTH": 0,
+    "KNIGHT_PURCHASED_THIS_TURN": 0,
+    "MONOPOLY_PURCHASED_THIS_TURN": 0,
+    "YEAR_OF_PLENTY_PURCHASED_THIS_TURN": 0,
+    "ROAD_BUILDING_PURCHASED_THIS_TURN": 0,
 }
 for resource in RESOURCES:
     PLAYER_INITIAL_STATE[f"{resource}_IN_HAND"] = 0
diff --git a/catanatron_core/catanatron/state_functions.py b/catanatron_core/catanatron/state_functions.py
index acf71799..4b71391d 100644
--- a/catanatron_core/catanatron/state_functions.py
+++ b/catanatron_core/catanatron/state_functions.py
@@ -225,9 +225,17 @@ def player_resource_freqdeck_contains(state, color, freqdeck):
 
 def player_can_play_dev(state, color, dev_card):
     key = player_key(state, color)
+
+    cards_in_hand = state.player_state[f"{key}_{dev_card}_IN_HAND"]
+    cards_purchased_this_turn = state.player_state[
+        f"{key}_{dev_card}_PURCHASED_THIS_TURN"
+    ]
+    playable_cards = cards_in_hand - cards_purchased_this_turn
+
     return (
         not state.player_state[f"{key}_HAS_PLAYED_DEVELOPMENT_CARD_IN_TURN"]
-        and state.player_state[f"{key}_{dev_card}_IN_HAND"] >= 1
+        # Must have at least 1 card that wasn't purchased this turn
+        and playable_cards > 0
     )
 
 
@@ -259,6 +267,9 @@ def buy_dev_card(state, color, dev_card):
     state.player_state[f"{key}_{dev_card}_IN_HAND"] += 1
     if dev_card == VICTORY_POINT:
         state.player_state[f"{key}_ACTUAL_VICTORY_POINTS"] += 1
+    else:
+        # Mark as purchased this turn
+        state.player_state[f"{key}_{dev_card}_PURCHASED_THIS_TURN"] += 1
 
     state.player_state[f"{key}_SHEEP_IN_HAND"] -= 1
     state.player_state[f"{key}_WHEAT_IN_HAND"] -= 1
@@ -334,3 +345,8 @@ def player_clean_turn(state, color):
     key = player_key(state, color)
     state.player_state[f"{key}_HAS_PLAYED_DEVELOPMENT_CARD_IN_TURN"] = False
     state.player_state[f"{key}_HAS_ROLLED"] = False
+    # Reset all purchased-this-turn counters
+    state.player_state[f"{key}_KNIGHT_PURCHASED_THIS_TURN"] = 0
+    state.player_state[f"{key}_MONOPOLY_PURCHASED_THIS_TURN"] = 0
+    state.player_state[f"{key}_YEAR_OF_PLENTY_PURCHASED_THIS_TURN"] = 0
+    state.player_state[f"{key}_ROAD_BUILDING_PURCHASED_THIS_TURN"] = 0
diff --git a/tests/test_game.py b/tests/test_game.py
index c00d7561..80b4f503 100644
--- a/tests/test_game.py
+++ b/tests/test_game.py
@@ -327,10 +327,7 @@ def test_play_road_building(fake_roll_dice):
     ):
         game.play_tick()
 
-    # roll not a 7
-    fake_roll_dice.return_value = (1, 2)
-    game.play_tick()  # roll
-
+    # Play Road Building before rolling
     game.execute(Action(p0.color, ActionType.PLAY_ROAD_BUILDING, None))
     assert game.state.is_road_building
     assert game.state.free_roads_available == 2
diff --git a/ui/src/pages/ActionsToolbar.js b/ui/src/pages/ActionsToolbar.js
index 74285758..2933c844 100644
--- a/ui/src/pages/ActionsToolbar.js
+++ b/ui/src/pages/ActionsToolbar.js
@@ -47,7 +47,7 @@ function PlayButtons() {
     [enqueueSnackbar, closeSnackbar]
   );
 
-  const { gameState, isPlayingMonopoly, isPlayingYearOfPlenty } = state;
+  const { gameState, isPlayingMonopoly, isPlayingYearOfPlenty, isRoadBuilding } = state;
   const key = playerKey(gameState, gameState.current_color);
   const isRoll =
     gameState.current_prompt === "PLAY_TURN" &&
@@ -198,7 +198,7 @@ function PlayButtons() {
   return (
     <>
       <OptionsButton
-        disabled={playableDevCardTypes.size === 0 || isPlayingYearOfPlenty}
+        disabled={playableDevCardTypes.size === 0 || isPlayingMonopoly || isPlayingYearOfPlenty || isRoadBuilding}
         menuListId="use-menu-list"
         icon={<SimCardIcon />}
         items={useItems}
@@ -206,7 +206,7 @@ function PlayButtons() {
         Use
       </OptionsButton>
       <OptionsButton
-        disabled={buildActionTypes.size === 0 || isPlayingYearOfPlenty}
+        disabled={buildActionTypes.size === 0 || isPlayingMonopoly || isPlayingYearOfPlenty || isRoadBuilding}
         menuListId="build-menu-list"
         icon={<BuildIcon />}
         items={buildItems}
@@ -214,7 +214,7 @@ function PlayButtons() {
         Buy
       </OptionsButton>
       <OptionsButton
-        disabled={tradeItems.length === 0 || isPlayingYearOfPlenty}
+        disabled={tradeItems.length === 0 || isPlayingMonopoly || isPlayingYearOfPlenty || isRoadBuilding}
         menuListId="trade-menu-list"
         icon={<AccountBalanceIcon />}
         items={tradeItems}
@@ -222,27 +222,27 @@ function PlayButtons() {
         Trade
       </OptionsButton>
       <Button
-        disabled={gameState.is_initial_build_phase}
+        disabled={gameState.is_initial_build_phase || isRoadBuilding}
         variant="contained"
         color="primary"
         startIcon={<NavigateNextIcon />}
         onClick={
-          isRoll
-            ? rollAction
-            : isDiscard
+          isDiscard
             ? proceedAction
             : isMoveRobber
             ? setIsMovingRobber
             : isPlayingYearOfPlenty || isPlayingMonopoly
             ? handleOpenResourceSelector
+            : isRoll
+            ? rollAction
             : endTurnAction
         }
       >
         {
-          isRoll ? "ROLL" : 
           isDiscard ? "DISCARD" : 
           isMoveRobber ? "ROB" : 
           isPlayingYearOfPlenty || isPlayingMonopoly ? "SELECT" : 
+          isRoll ? "ROLL" : 
           "END"
         }
       </Button>