diff --git a/client/src/Winner.tsx b/client/src/Winner.tsx
index b2957d6..82f287b 100644
--- a/client/src/Winner.tsx
+++ b/client/src/Winner.tsx
@@ -20,7 +20,14 @@ const Winner: React.FC<WinnerProps> = ({ winnerDismissed, setWinnerDismissed })
   const { lastJsonMessage, sendJsonMessage } = useContext(GlobalContext);
   const [winner, setWinner] = useState<any>(undefined);
   const [state, setState] = useState<string | undefined>(undefined);
-  const fields = useMemo(() => ["winner", "state"], []);
+  // Track the client's color so we can tell if the current user is an observer
+  // (observers don't have a color assigned). Observers should remain on the
+  // winner screen even if the server advances the global state to `lobby`.
+  const [color, setColor] = useState<string | undefined>(undefined);
+  // Include color/private so this component can determine whether the local
+  // session is an observer. We purposely request these minimal fields here
+  // to avoid coupling Winner to higher-level RoomView state handling.
+  const fields = useMemo(() => ["winner", "state", "color", "private"], []);
   useEffect(() => {
     if (!lastJsonMessage) {
       return;
@@ -33,11 +40,39 @@ const Winner: React.FC<WinnerProps> = ({ winnerDismissed, setWinnerDismissed })
         if ("winner" in data.update && !equal(data.update.winner, winner)) {
           setWinner(data.update.winner);
         }
+        // Keep track of our client color so we can special-case observer behavior
+        // (observers have no color). This allows an observer to stay on the
+        // winner screen even when the server moves the game back to the lobby.
+        if ("color" in data.update && data.update.color !== color) {
+          setColor(data.update.color);
+        }
         if ("state" in data.update && data.update.state !== state) {
+          // If the server leaves the winner state we normally clear the
+          // winner data. However, if the local user is an observer (no
+          // `color`) and they were viewing the winner screen, we keep the
+          // winner visible until they explicitly click "Go back to Lobby".
+          // This lets observers continue to view final game stats and the
+          // chat even as the server advances global state to `lobby`.
+          const isObserver = typeof color === "undefined" || color === null;
+          const leavingWinner = state === "winner" && data.update.state !== "winner";
+
           if (data.update.state !== "winner") {
-            setWinner(undefined);
+            if (isObserver && leavingWinner) {
+              // OBSERVER SPECIAL CASE: don't clear `winner` here. Still update
+              // the internal `state` so other parts of the UI know the server
+              // state changed, but keep rendering the winner panel for the
+              // observer until they click the button.
+            } else {
+              setWinner(undefined);
+            }
           }
-          setWinnerDismissed(false);
+
+          // Only reset the dismissed flag when the server re-enters winner
+          // (otherwise preserve user's dismissal choice).
+          if (data.update.state === "winner") {
+            setWinnerDismissed(false);
+          }
+
           setState(data.update.state);
         }
         break;
@@ -58,8 +93,17 @@ const Winner: React.FC<WinnerProps> = ({ winnerDismissed, setWinnerDismissed })
   const quitClicked = useCallback(() => {
     if (!winnerDismissed) {
       setWinnerDismissed(true);
+      // Tell server we want to go back to the lobby. Also immediately
+      // request the latest room/game fields so the client receives the
+      // updated lobby/game state and can continue observing the current
+      // game id. This helps observers remain connected to the same game
+      // record after the server transitions them.
+      sendJsonMessage({ type: "goto-lobby" });
       sendJsonMessage({
-        type: "goto-lobby",
+        type: "get",
+        // Request a conservative set of fields required to continue
+        // observing the current game/lobby state.
+        fields: ["id", "state", "color", "private", "players"],
       });
     }
   }, [sendJsonMessage, winnerDismissed, setWinnerDismissed]);
diff --git a/server/ai/app.ts b/server/ai/app.ts
index 5c70acd..ef25ffe 100644
--- a/server/ai/app.ts
+++ b/server/ai/app.ts
@@ -229,6 +229,7 @@ const tryProgress = (_received?: any): any => {
 
 let sleeping = false;
 let paused = false;
+let winnerAnnounced = false;
 
 const sleep = async (delay: number): Promise<void> => {
   if (sleeping) {
@@ -346,6 +347,78 @@ const isMatch = (input: any, received: any): boolean => {
   return true;
 };
 
+// Helper: deep clone/compare simple JSON-able values
+const deepClone = (v: any) => {
+  try { return JSON.parse(JSON.stringify(v)); } catch (e) { return v; }
+};
+// Stable stringify: recursively sort object keys so output is deterministic
+const stableStringify = (v: any): string => {
+  if (v === null) return 'null';
+  const t = typeof v;
+  if (t === 'number' || t === 'boolean' || t === 'string') return JSON.stringify(v);
+  if (Array.isArray(v)) {
+    return '[' + v.map((el) => stableStringify(el)).join(',') + ']';
+  }
+  if (t === 'object') {
+    const keys = Object.keys(v).sort();
+    return '{' + keys.map(k => JSON.stringify(k) + ':' + stableStringify((v as any)[k])).join(',') + '}';
+  }
+  // fallback
+  try { return JSON.stringify(v); } catch (e) { return String(v); }
+};
+
+const deepEqual = (a: any, b: any) => {
+  try { return stableStringify(a) === stableStringify(b); } catch (e) { return a === b; }
+};
+
+// Helper: get value at dot-separated path (path may be array or string)
+const getAtPath = (obj: any, path: string): any => {
+  if (!path) return undefined;
+  const parts = path.split('.');
+  let cur: any = obj;
+  for (let i = 0; i < parts.length; i++) {
+    if (cur === undefined || cur === null) return undefined;
+    const p = parts[i];
+    // @ts-ignore - dynamic index; we've checked cur for null/undefined
+    cur = (cur as any)[p];
+  }
+  return cur;
+};
+
+// Helper: collect all leaf paths from waitingFor object (returns dot-separated)
+const collectLeafPaths = (obj: any, prefix = ''): string[] => {
+  const paths: string[] = [];
+  if (obj === anyValue || obj === undefined) {
+    // leaf
+    if (prefix) paths.push(prefix);
+    return paths;
+  }
+  if (typeof obj !== 'object' || obj === null) {
+    if (prefix) paths.push(prefix);
+    return paths;
+  }
+  for (const k of Object.keys(obj)) {
+    const next = prefix ? `${prefix}.${k}` : k;
+    paths.push(...collectLeafPaths(obj[k], next));
+  }
+  return paths;
+};
+
+// Helper: check if msg.update explicitly contains the full path (leaf present in the incremental update)
+const msgUpdateContainsPath = (update: any, path: string): boolean => {
+  if (!update) return false;
+  const parts = path.split('.');
+  let cur: any = update;
+  for (let i = 0; i < parts.length; i++) {
+    if (cur === undefined || cur === null || typeof cur !== 'object') return false;
+    const key: PropertyKey = parts[i] as PropertyKey;
+    if (!Object.prototype.hasOwnProperty.call(cur, key)) return false;
+    // @ts-ignore - dynamic index guarded by previous checks
+    cur = (cur as any)[key];
+  }
+  return true;
+};
+
 const processLobby = (received: any): any => {
   /*
    * Lobby flow notes:
@@ -723,22 +796,120 @@ const processTrade = async (received?: any): Promise<any> => {
     gives: [give],
     gets: [get]
   };
+  // Helper: can our private resources satisfy a list of required give items?
+  const privateCanGive = (items: Array<any>): boolean => {
+    if (!game.private) return false;
+    for (let i = 0; i < (items || []).length; i++) {
+      const it = items[i];
+      if (!it) continue;
+      if (it.type === 'bank') {
+        // bank entries refer to a give type in our own player.gives; treat as not satisfiable here
+        return false;
+      }
+      const have = Number(game.private[it.type] || 0);
+      if (have < (it.count || 0)) return false;
+    }
+    return true;
+  };
 
+  // Helper: do two offers represent matching terms (p.gives == myGets && p.gets == myGives)
+  const offersMatch = (p: any, myOffer: any): boolean => {
+    if (!p || !myOffer) return false;
+    // compare lengths first
+    if ((p.gives || []).length !== (myOffer.gets || []).length) return false;
+    if ((p.gets || []).length !== (myOffer.gives || []).length) return false;
+    // each give in p must match a get in myOffer
+    for (let i = 0; i < (p.gives || []).length; i++) {
+      const g = p.gives[i];
+      let found = false;
+      for (let j = 0; j < (myOffer.gets || []).length; j++) {
+        const mg = myOffer.gets[j];
+        if (g.type === mg.type && g.count === mg.count) {
+          found = true;
+          break;
+        }
+      }
+      if (!found) return false;
+    }
+    for (let i = 0; i < (p.gets || []).length; i++) {
+      const g = p.gets[i];
+      let found = false;
+      for (let j = 0; j < (myOffer.gives || []).length; j++) {
+        const mg = myOffer.gives[j];
+        if (g.type === mg.type && g.count === mg.count) {
+          found = true;
+          break;
+        }
+      }
+      if (!found) return false;
+    }
+    return true;
+  };
+
+  // If there's a current turn-level offer, decide how to respond.
   if (received && received.turn && received.turn.offer) {
-    send({
-      type: 'trade',
-      action: 'accept',
-      offer: {
-        name: 'The bank',
-        gets: [{ type: get.type, count: 1 }],
-        gives: [{ type: give.type, count: give.count }]
+    const turnOffer = received.turn.offer;
+
+    // If the offer originates from another player (not the bank), then we (as the active player)
+    // should accept if we can satisfy the terms, otherwise explicitly reject.
+    if (turnOffer.name && turnOffer.name !== 'The bank') {
+      // Active player accepting other player's offer must be able to give what that player requests (offer.gets)
+      if (privateCanGive(turnOffer.gets || [])) {
+        send({ type: 'trade', action: 'accept', offer: turnOffer });
+        return { turn: { actions: anyValue } };
+      } else {
+        send({ type: 'trade', action: 'reject', offer: turnOffer });
+        return { turn: anyValue };
       }
-    });
-    return {
-      turn: {
-        actions: anyValue
+    }
+
+    // If the current offer is a bank offer, wait to allow other players to respond
+    // and prefer player trades over the bank.
+    const TRADE_RESPONSE_DELAY_MS = 15000;
+    await new Promise(r => setTimeout(r, TRADE_RESPONSE_DELAY_MS));
+
+    // Find our own player entry in the received players (our proposed offer)
+    const myEntry = (received.players && received.players[game.color]) || null;
+    const myOffer = myEntry && (myEntry.gives || myEntry.gets) ? { gives: myEntry.gives, gets: myEntry.gets, name: myEntry.name, color: myEntry.color } : null;
+
+    if (myOffer && myOffer.gives && myOffer.gives.length && myOffer.gets && myOffer.gets.length) {
+      // Scan other players to see if any submitted a matching counter-offer. If found and they can meet it,
+      // accept that player trade. If they can't meet it, explicitly reject their offer.
+      for (const color in (received.players || {})) {
+        if (!Object.prototype.hasOwnProperty.call(received.players, color)) continue;
+        const p = received.players[color];
+        if (!p || p.color === game.color) continue;
+        if (p.status !== 'Active') continue;
+        if (!p.gives || !p.gets) continue;
+        if (!offersMatch(p, myOffer)) continue;
+
+        // If the candidate player requests resources that we can provide, accept their offer.
+        if (privateCanGive(p.gets || [])) {
+          send({ type: 'trade', action: 'accept', offer: { name: p.name, color: p.color, gives: p.gives, gets: p.gets } });
+          return { turn: { actions: anyValue } };
+        } else {
+          // Cannot meet their terms — explicitly reject so the server will know.
+          send({ type: 'trade', action: 'reject', offer: { name: p.name, color: p.color, gives: p.gives, gets: p.gets } });
+        }
       }
-    };
+    }
+
+    // If no player trades were accepted, fall back to the bank trade (if we can still give the required resources).
+    if (privateCanGive([{ type: give.type, count: give.count }])) {
+      send({
+        type: 'trade',
+        action: 'accept',
+        offer: {
+          name: 'The bank',
+          gets: [{ type: get.type, count: 1 }],
+          gives: [{ type: give.type, count: give.count }]
+        }
+      });
+      return { turn: { actions: anyValue } };
+    }
+
+    // If we cannot satisfy the bank trade, do nothing this cycle.
+    return { turn: anyValue };
   }
 
   /* Initiate offer... */
@@ -984,7 +1155,96 @@ const message = async (data: WebSocket.Data): Promise<void> => {
     break;
 
   case 'game-update':
+    // Preserve previous snapshot to detect whether waited-for fields actually changed
+    const oldGameSnapshot = deepClone(game);
     Object.assign(game, msg.update || {});
+    // If the server just announced a winner, send a congratulatory chat
+    // and then dismiss the winner dialog by navigating back to the lobby.
+    if (msg.update && (msg.update.winner || msg.update.state === 'winner')) {
+      // If we got the full winner payload, use it. Otherwise request it from the server.
+      if (msg.update.winner) {
+        const w = msg.update.winner as any;
+        if (!winnerAnnounced) {
+          let message = '';
+          try {
+            // If we won, be witty. Use turns/points if available.
+            if (w.name === name) {
+              const pts = w.points !== undefined ? w.points : 'many';
+              const turns = w.turns !== undefined ? w.turns : 'a few';
+              message = `Victory! I won with ${pts} points after ${turns} turns. Beep boop — humility.exe not found.`;
+            } else {
+              const pts = w.points !== undefined ? ` with ${w.points} points` : '';
+              message = `Congratulations ${w.name}${pts}! Well played.`;
+            }
+          } catch (e) {
+            message = `Congratulations ${w.name || 'winner'}!`;
+          }
+          send({ type: 'chat', message });
+          // After a short pause show the lobby (dismiss winner dialog)
+          setTimeout(() => {
+            try {
+              send({ type: 'goto-lobby' });
+              // Immediately request lobby information so we can decide whether to
+              // auto-start (startOnFull) as soon as the server transitions back
+              // to the lobby. This avoids waiting for an unrelated update cycle.
+              setTimeout(() => {
+                try {
+                  send({ type: 'get', fields: ['players', 'participants', 'unselected', 'state'] });
+                } catch (err) {
+                  console.warn('Failed to request lobby fields', err);
+                }
+              }, 250);
+            } catch (err) {
+              console.warn('Failed to send goto-lobby', err);
+            }
+          }, 1200);
+          winnerAnnounced = true;
+        }
+      } else {
+        // We were notified the state is 'winner' but didn't receive the winner object.
+        // Request the winner field from the server. If it arrives shortly, the
+        // handler above will process it. Otherwise fall back to a generic message
+        // and return to the lobby.
+        try {
+          send({ type: 'get', fields: ['winner'] });
+        } catch (err) {
+          console.warn('Failed to request winner field', err);
+        }
+
+        // Fallback after a short wait if full winner info doesn't arrive.
+        setTimeout(() => {
+          if (winnerAnnounced) return;
+          let msgText = 'Congratulations to the winner!';
+          try {
+            // If we have some partial info in game, try to include it
+            if (game && game.turn && game.turn.name) {
+              msgText = `Congratulations ${game.turn.name}!`;
+            }
+          } catch (e) {
+            // ignore
+          }
+          send({ type: 'chat', message: msgText });
+          try {
+            send({ type: 'goto-lobby' });
+            // Ask for lobby state so we can react quickly (claim slot / auto-start)
+            setTimeout(() => {
+              try {
+                send({ type: 'get', fields: ['players', 'participants', 'unselected', 'state'] });
+              } catch (err) {
+                console.warn('Failed to request lobby fields (fallback)', err);
+              }
+            }, 250);
+          } catch (err) {
+            console.warn('Failed to send goto-lobby (fallback)', err);
+          }
+          winnerAnnounced = true;
+        }, 2000);
+      }
+    }
+      // If the server clears the winner/state, reset our announced flag so we can handle future games
+      if (msg.update && typeof msg.update.state !== 'undefined' && msg.update.state !== 'winner') {
+        winnerAnnounced = false;
+      }
     if (msg.update && msg.update.chat) {
       let newState = paused;
       const rePause = new RegExp(`${name}: pause`, 'i');
@@ -999,16 +1259,53 @@ const message = async (data: WebSocket.Data): Promise<void> => {
     if (sleeping) { if (waitingFor) Object.assign(received, msg.update); console.log(`${name} - sleeping`); return; }
 
     if (waitingFor) {
+      // Accumulate recent update fields for debugging
       Object.assign(received, msg.update);
-      if (!isMatch(waitingFor, received)) {
+
+      // First ensure presence in the merged snapshot
+      if (!isMatch(waitingFor, game)) {
         if (game.turn && game.turn.robberInAction) { console.log(`${name} - robber in action! Must check discards...`); } else { return; }
-      } else {
-        console.log(`${name} - received match - received: `, msg.update);
-        console.log(`${name} - going to sleep`);
-        await sleep(1000 + Math.random() * 500);
-        console.log(`${name} - waking up`);
-        waitingFor = undefined;
       }
+
+      // Now require that at least one of the waited-for leaf paths actually
+      // changed in this update (or was explicitly provided in msg.update).
+      // For leaves equal to `anyValue` we accept any change; for concrete
+      // values we accept only if the new value equals the concrete value.
+      const paths = collectLeafPaths(waitingFor);
+      let changeDetected = false;
+      for (const p of paths) {
+        const oldVal = getAtPath(oldGameSnapshot, p);
+        const newVal = getAtPath(game, p);
+
+        // If the incremental update explicitly contained the path, treat that as a change.
+        if (msg.update && msgUpdateContainsPath(msg.update, p)) {
+          changeDetected = true;
+          break;
+        }
+
+        // If old and new differ, that's a change
+        if (!deepEqual(oldVal, newVal)) {
+          changeDetected = true;
+          break;
+        }
+
+        // If the waiting leaf expects a concrete value (not anyValue) and the
+        // value already equals that concrete value, consider that satisfied
+        // only if it changed to that value in this update (above checks cover it).
+      }
+
+      if (!changeDetected) {
+        // No relevant change occurred in this update; continue waiting.
+        return;
+      }
+
+      // We found a change and presence is satisfied
+      const delay = 1000 + Math.random() * 500;
+      console.log(`${name} - received match - received: `, msg.update);
+      console.log(`${name} - going to sleep for ${Math.round(delay)}ms`);
+      await sleep(delay);
+      console.log(`${name} - waking up to wait for new socket messages...`);
+      waitingFor = undefined;
     }
 
     switch (game.state) {