diff --git a/apps/client/src/components/tab_manager.ts b/apps/client/src/components/tab_manager.ts
index 8799a80c2..fdd918722 100644
--- a/apps/client/src/components/tab_manager.ts
+++ b/apps/client/src/components/tab_manager.ts
@@ -149,18 +149,31 @@ export default class TabManager extends Component {
                 currentWin.contexts = filteredNoteContexts;
             } else {
                 if (savedWindows?.length >= MAX_SAVED_WINDOWS) {
-                    // Filter out a window to remove
+                    // Filter out the oldest entry
                     // 1) Never remove the "main" window
-                    // 2) Remove the window with the oldest creation time
-                    let windowToRemove: WindowState | null = null;
-                    for (const win of savedWindows) {
-                        if (win.windowId === "main") continue; // never remove main
-                        if (!windowToRemove || win.createdAt < windowToRemove.createdAt) {
-                            windowToRemove = win;
+                    // 2) Prefer removing the oldest closed window (closedAt !== 0)
+                    // 3) If no closed window exists, remove the window with the oldest created window
+                    let oldestClosedIndex = -1;
+                    let oldestClosedTime = Infinity;
+                    let oldestCreatedIndex = -1;
+                    let oldestCreatedTime = Infinity;
+                    savedWindows.forEach((w: WindowState, i: number) => {
+                        if (w.windowId === "main") return;
+                        if (w.closedAt !== 0) {
+                            if (w.closedAt < oldestClosedTime) {
+                                oldestClosedTime = w.closedAt;
+                                oldestClosedIndex = i;
+                            }
+                        } else {
+                            if (w.createdAt < oldestCreatedTime) {
+                                oldestCreatedTime = w.createdAt;
+                                oldestCreatedIndex = i;
+                            }
                         }
-                    }
-                    if (windowToRemove) {
-                        savedWindows.splice(savedWindows.indexOf(windowToRemove), 1);
+                    });
+                    const indexToRemove = oldestClosedIndex !== -1 ? oldestClosedIndex : oldestCreatedIndex;
+                    if (indexToRemove !== -1) {
+                        savedWindows.splice(indexToRemove, 1);
                     }
                 }
 
diff --git a/apps/desktop/src/main.ts b/apps/desktop/src/main.ts
index 8db9f91da..b96046209 100644
--- a/apps/desktop/src/main.ts
+++ b/apps/desktop/src/main.ts
@@ -127,7 +127,8 @@ async function onReady() {
                 }
             });
         }
-
+        
+        await normalizeOpenNoteContexts();
         tray.createTray();
     } else {
         await windowService.createSetupWindow();
@@ -136,6 +137,30 @@ async function onReady() {
     await windowService.registerGlobalShortcuts();
 }
 
+/**
+ * Some windows may have closed abnormally, leaving closedAt as 0 in openNoteContexts.
+ * This function normalizes those timestamps to the current time for correct sorting/filtering.
+ */
+async function normalizeOpenNoteContexts() {
+    const savedWindows = options.getOptionJson("openNoteContexts") || [];
+    const now = Date.now();
+
+    let changed = false;
+    for (const win of savedWindows) {
+        if (win.windowId !== "main" && win.closedAt === 0) {
+            win.closedAt = now;
+            changed = true;
+        }
+    }
+    
+    if (changed) {
+        const { default: cls } = (await import("@triliumnext/server/src/services/cls.js"));
+        cls.wrap(() => {
+            options.setOption("openNoteContexts", JSON.stringify(savedWindows));
+        })();
+    }
+}
+
 function getElectronLocale() {
     const uiLocale = options.getOptionOrNull("locale");
     const formattingLocale = options.getOptionOrNull("formattingLocale");
diff --git a/apps/server/src/services/tray.ts b/apps/server/src/services/tray.ts
index 8f373a293..3b0831aff 100644
--- a/apps/server/src/services/tray.ts
+++ b/apps/server/src/services/tray.ts
@@ -201,10 +201,11 @@ function updateTrayMenu() {
         const openedWindowIds = windowService.getAllWindowIds();
         const closedWindows = savedWindows
             .filter(win => !openedWindowIds.includes(win.windowId))
-            .sort((a, b) => { return b.closedAt - a.closedAt; });  // sort by time in descending order
+            .sort((a, b) => { return a.closedAt - b.closedAt; });  // sort by time in ascending order
         const menuItems: Electron.MenuItemConstructorOptions[] = [];
         
-        for (const win of closedWindows) {
+        for (let i = closedWindows.length - 1; i >= 0; i--) {
+            const win = closedWindows[i];
             const activeCtx = win.contexts.find(c => c.active === true);
             const activateNotePath = (activeCtx ?? win.contexts[0])?.notePath;
             const activateNoteId = activateNotePath?.split("/").pop() ?? null;