diff --git a/src/panels/config/automation/ha-automation-picker.ts b/src/panels/config/automation/ha-automation-picker.ts
index 62900a2798..28cd56dfc5 100644
--- a/src/panels/config/automation/ha-automation-picker.ts
+++ b/src/panels/config/automation/ha-automation-picker.ts
@@ -378,25 +378,42 @@ class HaAutomationPicker extends SubscribeMixin(LitElement) {
           ${this.hass.localize("ui.panel.config.category.editor.add")}
         </div>
       </ha-menu-item>`;
-    const labelItems = html` ${this._labels?.map((label) => {
+    const labelItems = html`${this._labels?.map((label) => {
         const color = label.color ? computeCssColor(label.color) : undefined;
+        const selected = this._selected.every((entityId) =>
+          this.hass.entities[entityId]?.labels.includes(label.label_id)
+        );
+        const partial =
+          !selected &&
+          this._selected.some((entityId) =>
+            this.hass.entities[entityId]?.labels.includes(label.label_id)
+          );
         return html`<ha-menu-item
           .value=${label.label_id}
+          .action=${selected ? "remove" : "add"}
           @click=${this._handleBulkLabel}
+          keep-open
         >
+          <ha-checkbox
+            slot="start"
+            .checked=${selected}
+            .indeterminate=${partial}
+            reducedTouchTarget
+          ></ha-checkbox>
           <ha-label style=${color ? `--color: ${color}` : ""}>
             ${label.icon
               ? html`<ha-icon slot="icon" .icon=${label.icon}></ha-icon>`
               : nothing}
             ${label.name}
           </ha-label>
-        </ha-menu-item> `;
-      })} <md-divider role="separator" tabindex="-1"></md-divider>
+        </ha-menu-item>`;
+      })}
+      <md-divider role="separator" tabindex="-1"></md-divider>
       <ha-menu-item @click=${this._createLabel}>
         <div slot="headline">
           ${this.hass.localize("ui.panel.config.labels.add_label")}
-        </div>
-      </ha-menu-item>`;
+        </div></ha-menu-item
+      >`;
 
     return html`
       <hass-tabs-subpage-data-table
@@ -1078,11 +1095,17 @@ class HaAutomationPicker extends SubscribeMixin(LitElement) {
 
   private async _handleBulkLabel(ev) {
     const label = ev.currentTarget.value;
+    const action = ev.currentTarget.action;
     const promises: Promise<UpdateEntityRegistryEntryResult>[] = [];
     this._selected.forEach((entityId) => {
       promises.push(
         updateEntityRegistryEntry(this.hass, entityId, {
-          labels: this.hass.entities[entityId].labels.concat(label),
+          labels:
+            action === "add"
+              ? this.hass.entities[entityId].labels.concat(label)
+              : this.hass.entities[entityId].labels.filter(
+                  (lbl) => lbl !== label
+                ),
         })
       );
     });
diff --git a/src/panels/config/devices/ha-config-devices-dashboard.ts b/src/panels/config/devices/ha-config-devices-dashboard.ts
index e47b567e3e..ba9630e2fa 100644
--- a/src/panels/config/devices/ha-config-devices-dashboard.ts
+++ b/src/panels/config/devices/ha-config-devices-dashboard.ts
@@ -546,23 +546,40 @@ export class HaConfigDeviceDashboard extends SubscribeMixin(LitElement) {
 
     const labelItems = html`${this._labels?.map((label) => {
         const color = label.color ? computeCssColor(label.color) : undefined;
+        const selected = this._selected.every((deviceId) =>
+          this.hass.devices[deviceId]?.labels.includes(label.label_id)
+        );
+        const partial =
+          !selected &&
+          this._selected.some((deviceId) =>
+            this.hass.devices[deviceId]?.labels.includes(label.label_id)
+          );
         return html`<ha-menu-item
           .value=${label.label_id}
+          .action=${selected ? "remove" : "add"}
           @click=${this._handleBulkLabel}
+          keep-open
         >
+          <ha-checkbox
+            slot="start"
+            .checked=${selected}
+            .indeterminate=${partial}
+            reducedTouchTarget
+          ></ha-checkbox>
           <ha-label style=${color ? `--color: ${color}` : ""}>
             ${label.icon
               ? html`<ha-icon slot="icon" .icon=${label.icon}></ha-icon>`
               : nothing}
             ${label.name}
           </ha-label>
-        </ha-menu-item> `;
-      })}<md-divider role="separator" tabindex="-1"></md-divider>
+        </ha-menu-item>`;
+      })}
+      <md-divider role="separator" tabindex="-1"></md-divider>
       <ha-menu-item @click=${this._createLabel}>
         <div slot="headline">
           ${this.hass.localize("ui.panel.config.labels.add_label")}
-        </div>
-      </ha-menu-item>`;
+        </div></ha-menu-item
+      >`;
 
     return html`
       <hass-tabs-subpage-data-table
@@ -783,11 +800,17 @@ export class HaConfigDeviceDashboard extends SubscribeMixin(LitElement) {
 
   private async _handleBulkLabel(ev) {
     const label = ev.currentTarget.value;
+    const action = ev.currentTarget.action;
     const promises: Promise<DeviceRegistryEntry>[] = [];
     this._selected.forEach((deviceId) => {
       promises.push(
         updateDeviceRegistryEntry(this.hass, deviceId, {
-          labels: this.hass.devices[deviceId].labels.concat(label),
+          labels:
+            action === "add"
+              ? this.hass.devices[deviceId].labels.concat(label)
+              : this.hass.devices[deviceId].labels.filter(
+                  (lbl) => lbl !== label
+                ),
         })
       );
     });
diff --git a/src/panels/config/entities/ha-config-entities.ts b/src/panels/config/entities/ha-config-entities.ts
index b4ae8573b9..ef9289b099 100644
--- a/src/panels/config/entities/ha-config-entities.ts
+++ b/src/panels/config/entities/ha-config-entities.ts
@@ -134,7 +134,7 @@ export class HaConfigEntities extends SubscribeMixin(LitElement) {
     { value: string[] | undefined; items: Set<string> | undefined }
   > = {};
 
-  @state() private _selectedEntities: string[] = [];
+  @state() private _selected: string[] = [];
 
   @state() private _expandedFilter?: string;
 
@@ -518,10 +518,26 @@ export class HaConfigEntities extends SubscribeMixin(LitElement) {
 
     const labelItems = html` ${this._labels?.map((label) => {
         const color = label.color ? computeCssColor(label.color) : undefined;
+        const selected = this._selected.every((entityId) =>
+          this.hass.entities[entityId]?.labels.includes(label.label_id)
+        );
+        const partial =
+          !selected &&
+          this._selected.some((entityId) =>
+            this.hass.entities[entityId]?.labels.includes(label.label_id)
+          );
         return html`<ha-menu-item
           .value=${label.label_id}
+          .action=${selected ? "remove" : "add"}
           @click=${this._handleBulkLabel}
+          keep-open
         >
+          <ha-checkbox
+            slot="start"
+            .checked=${selected}
+            .indeterminate=${partial}
+            reducedTouchTarget
+          ></ha-checkbox>
           <ha-label style=${color ? `--color: ${color}` : ""}>
             ${label.icon
               ? html`<ha-icon slot="icon" .icon=${label.icon}></ha-icon>`
@@ -529,12 +545,13 @@ export class HaConfigEntities extends SubscribeMixin(LitElement) {
             ${label.name}
           </ha-label>
         </ha-menu-item>`;
-      })}<md-divider role="separator" tabindex="-1"></md-divider>
+      })}
+      <md-divider role="separator" tabindex="-1"></md-divider>
       <ha-menu-item @click=${this._createLabel}>
         <div slot="headline">
           ${this.hass.localize("ui.panel.config.labels.add_label")}
-        </div>
-      </ha-menu-item>`;
+        </div></ha-menu-item
+      >`;
 
     return html`
       <hass-tabs-subpage-data-table
@@ -561,7 +578,7 @@ export class HaConfigEntities extends SubscribeMixin(LitElement) {
         }
         .filter=${this._filter}
         selectable
-        .selected=${this._selectedEntities.length}
+        .selected=${this._selected.length}
         @selection-changed=${this._handleSelectionChanged}
         clickable
         @clear-filter=${this._clearFilter}
@@ -903,14 +920,14 @@ ${
   private _handleSelectionChanged(
     ev: HASSDomEvent<SelectionChangedEvent>
   ): void {
-    this._selectedEntities = ev.detail.value;
+    this._selected = ev.detail.value;
   }
 
   private async _enableSelected() {
     showConfirmationDialog(this, {
       title: this.hass.localize(
         "ui.panel.config.entities.picker.enable_selected.confirm_title",
-        { number: this._selectedEntities.length }
+        { number: this._selected.length }
       ),
       text: this.hass.localize(
         "ui.panel.config.entities.picker.enable_selected.confirm_text"
@@ -921,7 +938,7 @@ ${
         let require_restart = false;
         let reload_delay = 0;
         await Promise.all(
-          this._selectedEntities.map(async (entity) => {
+          this._selected.map(async (entity) => {
             const result = await updateEntityRegistryEntry(this.hass, entity, {
               disabled_by: null,
             });
@@ -958,7 +975,7 @@ ${
     showConfirmationDialog(this, {
       title: this.hass.localize(
         "ui.panel.config.entities.picker.disable_selected.confirm_title",
-        { number: this._selectedEntities.length }
+        { number: this._selected.length }
       ),
       text: this.hass.localize(
         "ui.panel.config.entities.picker.disable_selected.confirm_text"
@@ -966,7 +983,7 @@ ${
       confirmText: this.hass.localize("ui.common.disable"),
       dismissText: this.hass.localize("ui.common.cancel"),
       confirm: () => {
-        this._selectedEntities.forEach((entity) =>
+        this._selected.forEach((entity) =>
           updateEntityRegistryEntry(this.hass, entity, {
             disabled_by: "user",
           })
@@ -980,7 +997,7 @@ ${
     showConfirmationDialog(this, {
       title: this.hass.localize(
         "ui.panel.config.entities.picker.hide_selected.confirm_title",
-        { number: this._selectedEntities.length }
+        { number: this._selected.length }
       ),
       text: this.hass.localize(
         "ui.panel.config.entities.picker.hide_selected.confirm_text"
@@ -988,7 +1005,7 @@ ${
       confirmText: this.hass.localize("ui.common.hide"),
       dismissText: this.hass.localize("ui.common.cancel"),
       confirm: () => {
-        this._selectedEntities.forEach((entity) =>
+        this._selected.forEach((entity) =>
           updateEntityRegistryEntry(this.hass, entity, {
             hidden_by: "user",
           })
@@ -999,7 +1016,7 @@ ${
   }
 
   private _unhideSelected() {
-    this._selectedEntities.forEach((entity) =>
+    this._selected.forEach((entity) =>
       updateEntityRegistryEntry(this.hass, entity, {
         hidden_by: null,
       })
@@ -1009,11 +1026,17 @@ ${
 
   private async _handleBulkLabel(ev) {
     const label = ev.currentTarget.value;
+    const action = ev.currentTarget.action;
     const promises: Promise<UpdateEntityRegistryEntryResult>[] = [];
-    this._selectedEntities.forEach((entityId) => {
+    this._selected.forEach((entityId) => {
       promises.push(
         updateEntityRegistryEntry(this.hass, entityId, {
-          labels: this.hass.entities[entityId].labels.concat(label),
+          labels:
+            action === "add"
+              ? this.hass.entities[entityId].labels.concat(label)
+              : this.hass.entities[entityId].labels.filter(
+                  (lbl) => lbl !== label
+                ),
         })
       );
     });
@@ -1021,21 +1044,19 @@ ${
   }
 
   private _removeSelected() {
-    const removeableEntities = this._selectedEntities.filter((entity) => {
+    const removeableEntities = this._selected.filter((entity) => {
       const stateObj = this.hass.states[entity];
       return stateObj?.attributes.restored;
     });
     showConfirmationDialog(this, {
       title: this.hass.localize(
         `ui.panel.config.entities.picker.remove_selected.confirm_${
-          removeableEntities.length !== this._selectedEntities.length
-            ? "partly_"
-            : ""
+          removeableEntities.length !== this._selected.length ? "partly_" : ""
         }title`,
         { number: removeableEntities.length }
       ),
       text:
-        removeableEntities.length === this._selectedEntities.length
+        removeableEntities.length === this._selected.length
           ? this.hass.localize(
               "ui.panel.config.entities.picker.remove_selected.confirm_text"
             )
@@ -1043,7 +1064,7 @@ ${
               "ui.panel.config.entities.picker.remove_selected.confirm_partly_text",
               {
                 removable: removeableEntities.length,
-                selected: this._selectedEntities.length,
+                selected: this._selected.length,
               }
             ),
       confirmText: this.hass.localize("ui.common.remove"),
diff --git a/src/panels/config/helpers/ha-config-helpers.ts b/src/panels/config/helpers/ha-config-helpers.ts
index 809f03a23e..a63b0c2a01 100644
--- a/src/panels/config/helpers/ha-config-helpers.ts
+++ b/src/panels/config/helpers/ha-config-helpers.ts
@@ -456,6 +456,7 @@ export class HaConfigHelpers extends SubscribeMixin(LitElement) {
           .value=${label.label_id}
           .action=${selected ? "remove" : "add"}
           @click=${this._handleBulkLabel}
+          keep-open
         >
           <ha-checkbox
             slot="start"
diff --git a/src/panels/config/scene/ha-scene-dashboard.ts b/src/panels/config/scene/ha-scene-dashboard.ts
index e88f76d1e8..990ab42656 100644
--- a/src/panels/config/scene/ha-scene-dashboard.ts
+++ b/src/panels/config/scene/ha-scene-dashboard.ts
@@ -374,10 +374,26 @@ class HaSceneDashboard extends SubscribeMixin(LitElement) {
       </ha-menu-item>`;
     const labelItems = html` ${this._labels?.map((label) => {
         const color = label.color ? computeCssColor(label.color) : undefined;
+        const selected = this._selected.every((entityId) =>
+          this.hass.entities[entityId]?.labels.includes(label.label_id)
+        );
+        const partial =
+          !selected &&
+          this._selected.some((entityId) =>
+            this.hass.entities[entityId]?.labels.includes(label.label_id)
+          );
         return html`<ha-menu-item
           .value=${label.label_id}
+          .action=${selected ? "remove" : "add"}
           @click=${this._handleBulkLabel}
+          keep-open
         >
+          <ha-checkbox
+            slot="start"
+            .checked=${selected}
+            .indeterminate=${partial}
+            reducedTouchTarget
+          ></ha-checkbox>
           <ha-label style=${color ? `--color: ${color}` : ""}>
             ${label.icon
               ? html`<ha-icon slot="icon" .icon=${label.icon}></ha-icon>`
@@ -385,12 +401,13 @@ class HaSceneDashboard extends SubscribeMixin(LitElement) {
             ${label.name}
           </ha-label>
         </ha-menu-item>`;
-      })}<md-divider role="separator" tabindex="-1"></md-divider>
+      })}
+      <md-divider role="separator" tabindex="-1"></md-divider>
       <ha-menu-item @click=${this._createLabel}>
         <div slot="headline">
           ${this.hass.localize("ui.panel.config.labels.add_label")}
-        </div>
-      </ha-menu-item>`;
+        </div></ha-menu-item
+      >`;
 
     return html`
       <hass-tabs-subpage-data-table
@@ -756,11 +773,17 @@ class HaSceneDashboard extends SubscribeMixin(LitElement) {
 
   private async _handleBulkLabel(ev) {
     const label = ev.currentTarget.value;
+    const action = ev.currentTarget.action;
     const promises: Promise<UpdateEntityRegistryEntryResult>[] = [];
     this._selected.forEach((entityId) => {
       promises.push(
         updateEntityRegistryEntry(this.hass, entityId, {
-          labels: this.hass.entities[entityId].labels.concat(label),
+          labels:
+            action === "add"
+              ? this.hass.entities[entityId].labels.concat(label)
+              : this.hass.entities[entityId].labels.filter(
+                  (lbl) => lbl !== label
+                ),
         })
       );
     });
diff --git a/src/panels/config/script/ha-script-picker.ts b/src/panels/config/script/ha-script-picker.ts
index c4be1b4e00..4d0242e934 100644
--- a/src/panels/config/script/ha-script-picker.ts
+++ b/src/panels/config/script/ha-script-picker.ts
@@ -384,12 +384,28 @@ class HaScriptPicker extends SubscribeMixin(LitElement) {
           ${this.hass.localize("ui.panel.config.category.editor.add")}
         </div>
       </ha-menu-item>`;
-    const labelItems = html` ${this._labels?.map((label) => {
+    const labelItems = html`${this._labels?.map((label) => {
         const color = label.color ? computeCssColor(label.color) : undefined;
+        const selected = this._selected.every((entityId) =>
+          this.hass.entities[entityId]?.labels.includes(label.label_id)
+        );
+        const partial =
+          !selected &&
+          this._selected.some((entityId) =>
+            this.hass.entities[entityId]?.labels.includes(label.label_id)
+          );
         return html`<ha-menu-item
           .value=${label.label_id}
+          .action=${selected ? "remove" : "add"}
           @click=${this._handleBulkLabel}
+          keep-open
+          reducedTouchTarget
         >
+          <ha-checkbox
+            slot="start"
+            .checked=${selected}
+            .indeterminate=${partial}
+          ></ha-checkbox>
           <ha-label style=${color ? `--color: ${color}` : ""}>
             ${label.icon
               ? html`<ha-icon slot="icon" .icon=${label.icon}></ha-icon>`
@@ -397,12 +413,13 @@ class HaScriptPicker extends SubscribeMixin(LitElement) {
             ${label.name}
           </ha-label>
         </ha-menu-item>`;
-      })}<md-divider role="separator" tabindex="-1"></md-divider>
+      })}
+      <md-divider role="separator" tabindex="-1"></md-divider>
       <ha-menu-item @click=${this._createLabel}>
         <div slot="headline">
           ${this.hass.localize("ui.panel.config.labels.add_label")}
-        </div>
-      </ha-menu-item>`;
+        </div></ha-menu-item
+      >`;
 
     return html`
       <hass-tabs-subpage-data-table
@@ -825,11 +842,17 @@ class HaScriptPicker extends SubscribeMixin(LitElement) {
 
   private async _handleBulkLabel(ev) {
     const label = ev.currentTarget.value;
+    const action = ev.currentTarget.action;
     const promises: Promise<UpdateEntityRegistryEntryResult>[] = [];
     this._selected.forEach((entityId) => {
       promises.push(
         updateEntityRegistryEntry(this.hass, entityId, {
-          labels: this.hass.entities[entityId].labels.concat(label),
+          labels:
+            action === "add"
+              ? this.hass.entities[entityId].labels.concat(label)
+              : this.hass.entities[entityId].labels.filter(
+                  (lbl) => lbl !== label
+                ),
         })
       );
     });