diff --git a/actix-web/src/app.rs b/actix-web/src/app.rs
index 1099731f3..c8d84a106 100644
--- a/actix-web/src/app.rs
+++ b/actix-web/src/app.rs
@@ -326,6 +326,20 @@ where
     /// Middleware can be applied similarly to individual `Scope`s and `Resource`s.
     /// See [`Scope::wrap`](crate::Scope::wrap) and [`Resource::wrap`].
     ///
+    /// # Middleware Ordering
+    ///
+    /// App-level middleware wraps the entire request router and **always executes before** any
+    /// [`Scope`](crate::Scope)-level or [`Resource`]-level middleware, regardless of the order in
+    /// which services are registered on the builder. Scope middleware cannot bypass or run before
+    /// App middleware.
+    ///
+    /// If you need certain routes to skip a middleware, apply that middleware at the
+    /// [`Scope`](crate::Scope) level instead of the `App` level.
+    ///
+    /// For more info on middleware ordering, see the
+    /// [Cross-Level Middleware Ordering](crate::middleware#cross-level-middleware-ordering)
+    /// section.
+    ///
     /// For more info on middleware take a look at the [`middleware` module][crate::middleware].
     ///
     /// # Examples
diff --git a/actix-web/src/middleware/mod.rs b/actix-web/src/middleware/mod.rs
index 4b5b3e896..527f7d8fc 100644
--- a/actix-web/src/middleware/mod.rs
+++ b/actix-web/src/middleware/mod.rs
@@ -15,7 +15,10 @@
 //! - Access external services (e.g., [sessions](https://docs.rs/actix-session), etc.)
 //!
 //! Middleware is registered for each [`App`], [`Scope`](crate::Scope), or
-//! [`Resource`](crate::Resource) and executed in opposite order as registration.
+//! [`Resource`](crate::Resource) and executed in opposite order as registration. Note that this
+//! reverse ordering applies _within_ a single level (`App`, `Scope`, or `Resource`). When
+//! middleware exists at multiple levels, App-level middleware always runs first. See
+//! [Cross-Level Middleware Ordering](#cross-level-middleware-ordering) for details.
 //!
 //! # Simple Middleware
 //!
@@ -120,6 +123,62 @@
 //! middleware are run in reverse order for [`App`] _and then_ in reverse order for the wrapped
 //! service.
 //!
+//! # Cross-Level Middleware Ordering
+//!
+//! When middleware is registered on _both_ an [`App`] and a [`Scope`](crate::Scope) (or
+//! [`Resource`](crate::Resource)), the App-level middleware **always** runs before the
+//! Scope/Resource-level middleware. This is because App-level middleware wraps the entire request
+//! router, and routing to a specific scope or resource happens _inside_ that middleware chain.
+//!
+//! ```plain
+//!                     Request
+//!                        ⭣
+//! ╭──────────────────────┼──────╮
+//! │ App Middleware       │      │
+//! │ ╭────────────────────┼─────╮│
+//! │ │ Router             │     ││
+//! │ │      ╭─────────────┼────╮││
+//! │ │      │ Scope MW    │    │││
+//! │ │      │ ╭───────────┼───╮│││
+//! │ │      │ │ Resource  │   ││││
+//! │ │      │ │ MW        │   ││││
+//! │ │      │ │ ╭─────────┼──╮││││
+//! │ │      │ │ │ Handler │  │││││
+//! │ │      │ │ ╰─────────┼──╯││││
+//! │ │      │ ╰───────────┼───╯│││
+//! │ │      ╰─────────────┼────╯││
+//! │ ╰────────────────────┼─────╯│
+//! ╰──────────────────────┼──────╯
+//!                        ⭣
+//!                     Response
+//! ```
+//!
+//! This means that a middleware applied to a [`Scope`](crate::Scope) **cannot** bypass or run
+//! before middleware applied to the enclosing [`App`]. For example, if authentication middleware
+//! is registered on `App`, a "bypass auth" middleware on a scope will not work because the App
+//! auth middleware has already executed by the time routing reaches that scope.
+//!
+//! If you need different middleware behavior for different groups of routes, apply middleware at
+//! the scope level rather than the app level:
+//!
+//! ```
+//! use actix_web::{web, middleware, App};
+//!
+//! // Instead of applying auth middleware at the App level and trying
+//! // to bypass it on certain scopes, apply it per-scope:
+//! let app = App::new()
+//!     .service(
+//!         web::scope("/api")
+//!             .wrap(middleware::DefaultHeaders::new()) // e.g., auth middleware
+//!             // ... api routes
+//!     )
+//!     .service(
+//!         web::scope("/public")
+//!             // no auth middleware here
+//!             // ... public routes
+//!     );
+//! ```
+//!
 //! # Middleware Traits
 //!
 //! ## `Transform<S, Req>`