diff --git a/apps/client/src/widgets/buttons/left_pane_toggle.ts b/apps/client/src/widgets/buttons/left_pane_toggle.ts
index 80725a3e8..99fa0530b 100644
--- a/apps/client/src/widgets/buttons/left_pane_toggle.ts
+++ b/apps/client/src/widgets/buttons/left_pane_toggle.ts
@@ -19,10 +19,10 @@ export default class LeftPaneToggleWidget extends CommandButtonWidget {
                 return "bx-sidebar";
             }
 
-            return options.is("leftPaneVisible") ? "bx-chevrons-left" : "bx-chevrons-right";
+            return this.currentLeftPaneVisible ? "bx-chevrons-left" : "bx-chevrons-right";
         };
 
-        this.settings.title = () => (options.is("leftPaneVisible") ? t("left_pane_toggle.hide_panel") : t("left_pane_toggle.show_panel"));
+        this.settings.title = () => (this.currentLeftPaneVisible ? t("left_pane_toggle.hide_panel") : t("left_pane_toggle.show_panel"));
 
         this.settings.command = () => (this.currentLeftPaneVisible ? "hideLeftPane" : "showLeftPane");
 
@@ -38,7 +38,9 @@ export default class LeftPaneToggleWidget extends CommandButtonWidget {
 
     entitiesReloadedEvent({ loadResults }: EventData<"entitiesReloaded">) {
         if (loadResults.isOptionReloaded("leftPaneVisible") && document.hasFocus()) {
-            this.currentLeftPaneVisible = options.is("leftPaneVisible");
+            // options.is("leftPaneVisible") changed — it may or may not be the same as currentLeftPaneVisible, but as long as the window is focused, the left pane visibility should be toggled.
+            // See PR description for detailed explanation of multi-window edge cases: https://github.com/TriliumNext/Notes/pull/1962
+            this.currentLeftPaneVisible = !this.currentLeftPaneVisible;        
             this.refreshIcon();
         }
     }
diff --git a/apps/client/src/widgets/containers/left_pane_container.ts b/apps/client/src/widgets/containers/left_pane_container.ts
index 2b8221553..c9016b8ae 100644
--- a/apps/client/src/widgets/containers/left_pane_container.ts
+++ b/apps/client/src/widgets/containers/left_pane_container.ts
@@ -4,20 +4,26 @@ import appContext, { type EventData } from "../../components/app_context.js";
 import type Component from "../../components/component.js";
 
 export default class LeftPaneContainer extends FlexContainer<Component> {
+    private currentLeftPaneVisible: boolean;
+    
     constructor() {
         super("column");
 
+        this.currentLeftPaneVisible = options.is("leftPaneVisible");
+
         this.id("left-pane");
         this.css("height", "100%");
         this.collapsible();
     }
 
     isEnabled() {
-        return super.isEnabled() && options.is("leftPaneVisible");
+        return super.isEnabled() && this.currentLeftPaneVisible;
     }
 
     entitiesReloadedEvent({ loadResults }: EventData<"entitiesReloaded">) {
         if (loadResults.isOptionReloaded("leftPaneVisible") && document.hasFocus()) {
+            // options.is("leftPaneVisible") changed — it may or may not be the same as currentLeftPaneVisible, but as long as the window is focused, the left pane visibility should be toggled.
+            this.currentLeftPaneVisible = !this.currentLeftPaneVisible;
             const visible = this.isEnabled();
             this.toggleInt(visible);