diff --git a/apps/web/src/app/vault/components/vault-items/vault-items.component.ts b/apps/web/src/app/vault/components/vault-items/vault-items.component.ts
index 3511257d6da..96c23d6dd19 100644
--- a/apps/web/src/app/vault/components/vault-items/vault-items.component.ts
+++ b/apps/web/src/app/vault/components/vault-items/vault-items.component.ts
@@ -260,9 +260,9 @@ export class VaultItemsComponent<C extends CipherViewLike> {
   }
 
   get isAllSelected() {
-    return this.editableItems
-      .slice(0, MaxSelectionCount)
-      .every((item) => this.selection.isSelected(item));
+    // Check selection against sorted items to match toggleAll() behavior
+    const sortedItems = this.getSortedEditableItems();
+    return sortedItems.slice(0, MaxSelectionCount).every((item) => this.selection.isSelected(item));
   }
 
   get isEmpty() {
@@ -376,9 +376,30 @@ export class VaultItemsComponent<C extends CipherViewLike> {
   }
 
   protected toggleAll() {
-    this.isAllSelected
-      ? this.selection.clear()
-      : this.selection.select(...this.editableItems.slice(0, MaxSelectionCount));
+    if (this.isAllSelected) {
+      this.selection.clear();
+    } else {
+      const sortedItems = this.getSortedEditableItems();
+      this.selection.select(...sortedItems.slice(0, MaxSelectionCount));
+    }
+  }
+
+  /**
+   * Returns editableItems sorted according to the current table sort configuration.
+   * This ensures bulk selection matches the visual order displayed to the user.
+   */
+  private getSortedEditableItems(): VaultItem<C>[] {
+    const currentSort = this.dataSource.sort;
+    const items = [...this.editableItems];
+
+    // If no sort function is set, return items in their original order (as displayed in table)
+    if (!currentSort || !currentSort.fn) {
+      return items;
+    }
+
+    // Apply sort function with direction modifier (matches TableDataSource.sortData behavior)
+    const directionModifier = currentSort.direction === "asc" ? 1 : -1;
+    return items.sort((a, b) => currentSort.fn(a, b, currentSort.direction) * directionModifier);
   }
 
   protected event(event: VaultItemEvent<C>) {
@@ -584,12 +605,13 @@ export class VaultItemsComponent<C extends CipherViewLike> {
    * Sorts VaultItems, grouping collections before ciphers, and sorting each group alphabetically by name.
    */
   protected sortByName = (a: VaultItem<C>, b: VaultItem<C>, direction: SortDirection) => {
-    // Collections before ciphers
-    const collectionCompare = this.prioritizeCollections(a, b, direction);
+    // Collections before ciphers (direction-independent)
+    const collectionCompare = this.prioritizeCollections(a, b);
     if (collectionCompare !== 0) {
       return collectionCompare;
     }
 
+    // Name comparison (direction-dependent, handled by directionModifier)
     return this.compareNames(a, b);
   };
 
@@ -611,8 +633,8 @@ export class VaultItemsComponent<C extends CipherViewLike> {
       return null;
     };
 
-    // Collections before ciphers
-    const collectionCompare = this.prioritizeCollections(a, b, direction);
+    // Collections before ciphers (direction-independent)
+    const collectionCompare = this.prioritizeCollections(a, b);
     if (collectionCompare !== 0) {
       return collectionCompare;
     }
@@ -655,8 +677,8 @@ export class VaultItemsComponent<C extends CipherViewLike> {
       return priorityMap[permission] ?? -1;
     };
 
-    // Collections before ciphers
-    const collectionCompare = this.prioritizeCollections(a, b, direction);
+    // Collections before ciphers (direction-independent)
+    const collectionCompare = this.prioritizeCollections(a, b);
     if (collectionCompare !== 0) {
       return collectionCompare;
     }
@@ -664,11 +686,12 @@ export class VaultItemsComponent<C extends CipherViewLike> {
     const priorityA = getPermissionPriority(a);
     const priorityB = getPermissionPriority(b);
 
-    // Higher priority first
+    // Higher priority first (direction-dependent, handled by directionModifier)
     if (priorityA !== priorityB) {
       return priorityA - priorityB;
     }
 
+    // Fallback to name comparison (direction-dependent, handled by directionModifier)
     return this.compareNames(a, b);
   };
 
@@ -679,22 +702,19 @@ export class VaultItemsComponent<C extends CipherViewLike> {
 
   /**
    * Sorts VaultItems by prioritizing collections over ciphers.
-   * Collections are always placed before ciphers, regardless of the sorting direction.
+   * Always returns -1 for collections before ciphers, regardless of sort direction.
+   * This comparison is direction-independent; the direction is applied separately via directionModifier.
    */
-  private prioritizeCollections(
-    a: VaultItem<C>,
-    b: VaultItem<C>,
-    direction: SortDirection,
-  ): number {
+  private prioritizeCollections(a: VaultItem<C>, b: VaultItem<C>): number {
     if (a.collection && !b.collection) {
-      return direction === "asc" ? -1 : 1;
+      return -1; // a (collection) comes before b (cipher)
     }
 
     if (!a.collection && b.collection) {
-      return direction === "asc" ? 1 : -1;
+      return 1; // b (collection) comes before a (cipher)
     }
 
-    return 0;
+    return 0; // Both are collections or both are ciphers
   }
 
   private hasPersonalItems(): boolean {