diff --git a/frappe/public/js/frappe/ui/sidebar/sidebar.js b/frappe/public/js/frappe/ui/sidebar/sidebar.js
index da50e3a0ae..34eaa85098 100644
--- a/frappe/public/js/frappe/ui/sidebar/sidebar.js
+++ b/frappe/public/js/frappe/ui/sidebar/sidebar.js
@@ -256,10 +256,16 @@ frappe.ui.Sidebar = class Sidebar {
 			this.wrapper.addClass("expanded");
 			// this.sidebar_expanded = false
 			direction = "left";
+			$('[data-toggle="tooltip"]').tooltip("dispose");
 		} else {
 			this.wrapper.removeClass("expanded");
 			// this.sidebar_expanded = true
 			direction = "right";
+			$('[data-toggle="tooltip"]').tooltip({
+				boundary: "window",
+				container: "body",
+				trigger: "hover",
+			});
 		}
 
 		localStorage.setItem("sidebar-expanded", this.sidebar_expanded);
@@ -311,33 +317,46 @@ frappe.ui.Sidebar = class Sidebar {
 	}
 
 	set_workspace_sidebar(router) {
-		let route = frappe.get_route();
-		if (frappe.get_route()[0] == "setup-wizard") return;
-		if (route[0] == "Workspaces") {
-			let workspace;
-			if (!route[1]) {
-				workspace = "My Workspaces";
-			} else {
-				workspace = route[1];
-			}
-
-			frappe.app.sidebar.setup(workspace);
-		} else if (route[0] == "List" || route[0] == "Form") {
-			let doctype = route[1];
-			let sidebars = this.get_correct_workspace_sidebars(doctype);
-			// prevents switching of the sidebar if one item is linked in two sidebars
-			if (sidebars.includes(this.workspace_title)) {
-				frappe.app.sidebar.setup(this.workspace_title);
-				return;
-			}
-			if (sidebars.length == 0) {
-				let module_name = router.meta?.module;
-				if (module_name) {
-					frappe.app.sidebar.setup(
-						this.sidebar_module_map[module_name][0] || module_name
-					);
+		try {
+			let route = frappe.get_route();
+			if (frappe.get_route()[0] == "setup-wizard") return;
+			if (route[0] == "Workspaces") {
+				let workspace;
+				if (!route[1]) {
+					workspace = "My Workspaces";
+				} else {
+					workspace = route[1];
 				}
-			} else {
+
+				frappe.app.sidebar.setup(workspace);
+			} else if (route[0] == "List" || route[0] == "Form") {
+				let doctype = route[1];
+				let sidebars = this.get_correct_workspace_sidebars(doctype);
+				// prevents switching of the sidebar if one item is linked in two sidebars
+				if (sidebars.includes(this.workspace_title)) {
+					frappe.app.sidebar.setup(this.workspace_title);
+					return;
+				}
+				if (sidebars.length == 0) {
+					let module_name = router.meta?.module;
+					if (module_name) {
+						frappe.app.sidebar.setup(
+							this.sidebar_module_map[module_name][0] || module_name
+						);
+					}
+				} else {
+					if (
+						this.workspace_title &&
+						sidebars.includes(this.workspace_title.toLowerCase())
+					) {
+						frappe.app.sidebar.setup(this.workspace_title.toLowerCase());
+					} else {
+						frappe.app.sidebar.setup(sidebars[0]);
+					}
+				}
+			} else if (route[0] == "query-report") {
+				let doctype = route[1];
+				let sidebars = this.get_correct_workspace_sidebars(doctype);
 				if (
 					this.workspace_title &&
 					sidebars.includes(this.workspace_title.toLowerCase())
@@ -347,14 +366,8 @@ frappe.ui.Sidebar = class Sidebar {
 					frappe.app.sidebar.setup(sidebars[0]);
 				}
 			}
-		} else if (route[0] == "query-report") {
-			let doctype = route[1];
-			let sidebars = this.get_correct_workspace_sidebars(doctype);
-			if (this.workspace_title && sidebars.includes(this.workspace_title.toLowerCase())) {
-				frappe.app.sidebar.setup(this.workspace_title.toLowerCase());
-			} else {
-				frappe.app.sidebar.setup(sidebars[0]);
-			}
+		} catch (e) {
+			console.log(e);
 		}
 
 		this.set_active_workspace_item();
@@ -393,6 +406,7 @@ frappe.ui.Sidebar = class Sidebar {
 	toggle_editing_mode() {
 		const me = this;
 		if (this.edit_mode) {
+			this.open();
 			this.wrapper.attr("data-mode", "edit");
 			this.new_sidebar_items = Array.from(me.workspace_sidebar_items);
 			$(this.active_item).removeClass("active-sidebar");
diff --git a/frappe/public/js/frappe/ui/sidebar/sidebar_item.html b/frappe/public/js/frappe/ui/sidebar/sidebar_item.html
index f448294c1d..f58db7f4cf 100644
--- a/frappe/public/js/frappe/ui/sidebar/sidebar_item.html
+++ b/frappe/public/js/frappe/ui/sidebar/sidebar_item.html
@@ -2,11 +2,16 @@
     class="sidebar-item-container {%= item.is_editable ? 'is-draggable' : '' %} {% if (item.type == 'Section Break') { %}section-item{% } %}"
     item-name="{{ item.label }}"
     data-id="{{ item.label }}"
+    title="{{ item.label }}"
+    data-toggle="tooltip"
+    data-placement="right"
 >
-    <div class="standard-sidebar-item {%= item.indent ? 'indent' : '' %}">
+    <div
+        class="standard-sidebar-item {%= item.indent ? 'indent' : '' %}">
+
         {% if (item.type == "Section Break" && item.indent != 1) { %}
             <div class="divider hidden"></div>
-            <div class="item-anchor section-break" title="{{ item.label }}">
+            <div class="item-anchor section-break">
                 <span class="sidebar-item-label">{{ item.label }}</span>
                 <div class="sidebar-item-control"></div>
             </div>
@@ -19,7 +24,6 @@
                 href="{{ path }}"
                 target="{%= item.link_type === "URL" ? "_blank" : "" %}"
                 class="item-anchor"
-                title="{{ item.label }}"
             >
                 {% let icon = item.icon %}
                 {% if (item.show_arrow) { %}
diff --git a/frappe/public/js/frappe/ui/sidebar/sidebar_item.js b/frappe/public/js/frappe/ui/sidebar/sidebar_item.js
index 58f3e4b6b6..0a7411827a 100644
--- a/frappe/public/js/frappe/ui/sidebar/sidebar_item.js
+++ b/frappe/public/js/frappe/ui/sidebar/sidebar_item.js
@@ -186,6 +186,9 @@ frappe.ui.sidebar_item.TypeSectionBreak = class SectionBreakSidebarItem extends
 				$(me.wrapper.find(".divider")).removeClass("hidden");
 				me.old_state = me.collapsed;
 				me.open();
+				if (me.item.indent) {
+					me.close();
+				}
 			}
 		});
 	}
diff --git a/frappe/public/scss/desk/sidebar.scss b/frappe/public/scss/desk/sidebar.scss
index c50acb3be1..8b4de84351 100644
--- a/frappe/public/scss/desk/sidebar.scss
+++ b/frappe/public/scss/desk/sidebar.scss
@@ -238,7 +238,6 @@
 	gap: 0px !important;
 }
 .section-item {
-	margin-top: 5px;
 	.standard-sidebar-item {
 		align-items: center;
 	}