diff --git a/axum-macros/CHANGELOG.md b/axum-macros/CHANGELOG.md
index 0af5e8f4..c1b438d9 100644
--- a/axum-macros/CHANGELOG.md
+++ b/axum-macros/CHANGELOG.md
@@ -7,7 +7,10 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 # Unreleased
 
-- None.
+- **added:** In `debug_handler`, check if `Request` is used as non-final extractor ([#1035])
+- **added:** In `debug_handler`, check if multiple `Path` extractors are used ([#1035])
+
+[#1035]: https://github.com/tokio-rs/axum/pull/1035
 
 # 0.2.1 (10. May, 2022)
 
diff --git a/axum-macros/Cargo.toml b/axum-macros/Cargo.toml
index 73740472..96f6d91f 100644
--- a/axum-macros/Cargo.toml
+++ b/axum-macros/Cargo.toml
@@ -24,5 +24,6 @@ axum = { path = "../axum", version = "0.5", features = ["headers"] }
 axum-extra = { path = "../axum-extra", version = "0.3", features = ["typed-routing"] }
 rustversion = "1.0"
 serde = { version = "1.0", features = ["derive"] }
+syn = { version = "1.0", features = ["full", "extra-traits"] }
 tokio = { version = "1.0", features = ["full"] }
 trybuild = "1.0"
diff --git a/axum-macros/src/debug_handler.rs b/axum-macros/src/debug_handler.rs
index e55ed081..3404cda6 100644
--- a/axum-macros/src/debug_handler.rs
+++ b/axum-macros/src/debug_handler.rs
@@ -2,21 +2,24 @@ use proc_macro2::TokenStream;
 use quote::{format_ident, quote, quote_spanned};
 use syn::{parse::Parse, spanned::Spanned, FnArg, ItemFn, Token, Type};
 
-pub(crate) fn expand(attr: Attrs, item_fn: ItemFn) -> syn::Result<TokenStream> {
-    check_extractor_count(&item_fn)?;
+pub(crate) fn expand(attr: Attrs, item_fn: ItemFn) -> TokenStream {
+    let check_extractor_count = check_extractor_count(&item_fn);
+    let check_request_last_extractor = check_request_last_extractor(&item_fn);
+    let check_path_extractor = check_path_extractor(&item_fn);
 
     let check_inputs_impls_from_request = check_inputs_impls_from_request(&item_fn, &attr.body_ty);
     let check_output_impls_into_response = check_output_impls_into_response(&item_fn);
     let check_future_send = check_future_send(&item_fn);
 
-    let tokens = quote! {
+    quote! {
         #item_fn
+        #check_extractor_count
+        #check_request_last_extractor
+        #check_path_extractor
         #check_inputs_impls_from_request
         #check_output_impls_into_response
         #check_future_send
-    };
-
-    Ok(tokens)
+    }
 }
 
 pub(crate) struct Attrs {
@@ -45,18 +48,79 @@ impl Parse for Attrs {
     }
 }
 
-fn check_extractor_count(item_fn: &ItemFn) -> syn::Result<()> {
+fn check_extractor_count(item_fn: &ItemFn) -> Option<TokenStream> {
     let max_extractors = 16;
     if item_fn.sig.inputs.len() <= max_extractors {
-        Ok(())
+        None
     } else {
-        Err(syn::Error::new_spanned(
-                &item_fn.sig.inputs,
-                format!(
-                    "Handlers cannot take more than {} arguments. Use `(a, b): (ExtractorA, ExtractorA)` to further nest extractors",
-                    max_extractors,
+        let error_message = format!(
+            "Handlers cannot take more than {} arguments. \
+            Use `(a, b): (ExtractorA, ExtractorA)` to further nest extractors",
+            max_extractors,
+        );
+        let error = syn::Error::new_spanned(&item_fn.sig.inputs, error_message).to_compile_error();
+        Some(error)
+    }
+}
+
+fn extractor_idents(item_fn: &ItemFn) -> impl Iterator<Item = (usize, &syn::FnArg, &syn::Ident)> {
+    item_fn
+        .sig
+        .inputs
+        .iter()
+        .enumerate()
+        .filter_map(|(idx, fn_arg)| match fn_arg {
+            FnArg::Receiver(_) => None,
+            FnArg::Typed(pat_type) => {
+                if let Type::Path(type_path) = &*pat_type.ty {
+                    type_path
+                        .path
+                        .segments
+                        .last()
+                        .map(|segment| (idx, fn_arg, &segment.ident))
+                } else {
+                    None
+                }
+            }
+        })
+}
+
+fn check_request_last_extractor(item_fn: &ItemFn) -> Option<TokenStream> {
+    let request_extractor_ident =
+        extractor_idents(item_fn).find(|(_, _, ident)| *ident == "Request");
+
+    if let Some((idx, fn_arg, _)) = request_extractor_ident {
+        if idx != item_fn.sig.inputs.len() - 1 {
+            return Some(
+                syn::Error::new_spanned(fn_arg, "`Request` extractor should always be last")
+                    .to_compile_error(),
+            );
+        }
+    }
+
+    None
+}
+
+fn check_path_extractor(item_fn: &ItemFn) -> TokenStream {
+    let path_extractors = extractor_idents(item_fn)
+        .filter(|(_, _, ident)| *ident == "Path")
+        .collect::<Vec<_>>();
+
+    if path_extractors.len() > 1 {
+        path_extractors
+            .into_iter()
+            .map(|(_, arg, _)| {
+                syn::Error::new_spanned(
+                    arg,
+                    "Multiple parameters must be extracted with a tuple \
+                    `Path<(_, _)>` or a struct `Path<YourParams>`, not by applying \
+                    multiple `Path<_>` extractors",
                 )
-            ))
+                .to_compile_error()
+            })
+            .collect()
+    } else {
+        quote! {}
     }
 }
 
diff --git a/axum-macros/src/lib.rs b/axum-macros/src/lib.rs
index 22e9a99a..a44a14db 100644
--- a/axum-macros/src/lib.rs
+++ b/axum-macros/src/lib.rs
@@ -407,7 +407,7 @@ where
 
 fn expand_attr_with<F, A, I, K>(attr: TokenStream, input: TokenStream, f: F) -> TokenStream
 where
-    F: FnOnce(A, I) -> syn::Result<K>,
+    F: FnOnce(A, I) -> K,
     A: Parse,
     I: Parse,
     K: ToTokens,
@@ -415,7 +415,7 @@ where
     let expand_result = (|| {
         let attr = syn::parse(attr)?;
         let input = syn::parse(input)?;
-        f(attr, input)
+        Ok(f(attr, input))
     })();
     expand(expand_result)
 }
diff --git a/axum-macros/tests/debug_handler/fail/multiple_paths.rs b/axum-macros/tests/debug_handler/fail/multiple_paths.rs
new file mode 100644
index 00000000..0f4fd90e
--- /dev/null
+++ b/axum-macros/tests/debug_handler/fail/multiple_paths.rs
@@ -0,0 +1,7 @@
+use axum::extract::Path;
+use axum_macros::debug_handler;
+
+#[debug_handler]
+async fn handler(_: Path<String>, _: Path<String>) {}
+
+fn main() {}
diff --git a/axum-macros/tests/debug_handler/fail/multiple_paths.stderr b/axum-macros/tests/debug_handler/fail/multiple_paths.stderr
new file mode 100644
index 00000000..3eb57c9e
--- /dev/null
+++ b/axum-macros/tests/debug_handler/fail/multiple_paths.stderr
@@ -0,0 +1,11 @@
+error: Multiple parameters must be extracted with a tuple `Path<(_, _)>` or a struct `Path<YourParams>`, not by applying multiple `Path<_>` extractors
+ --> tests/debug_handler/fail/multiple_paths.rs:5:18
+  |
+5 | async fn handler(_: Path<String>, _: Path<String>) {}
+  |                  ^^^^^^^^^^^^^^^
+
+error: Multiple parameters must be extracted with a tuple `Path<(_, _)>` or a struct `Path<YourParams>`, not by applying multiple `Path<_>` extractors
+ --> tests/debug_handler/fail/multiple_paths.rs:5:35
+  |
+5 | async fn handler(_: Path<String>, _: Path<String>) {}
+  |                                   ^^^^^^^^^^^^^^^
diff --git a/axum-macros/tests/debug_handler/fail/request_not_last.rs b/axum-macros/tests/debug_handler/fail/request_not_last.rs
new file mode 100644
index 00000000..153d35ef
--- /dev/null
+++ b/axum-macros/tests/debug_handler/fail/request_not_last.rs
@@ -0,0 +1,7 @@
+use axum::{body::Body, extract::Extension, http::Request};
+use axum_macros::debug_handler;
+
+#[debug_handler]
+async fn handler(_: Request<Body>, _: Extension<String>) {}
+
+fn main() {}
diff --git a/axum-macros/tests/debug_handler/fail/request_not_last.stderr b/axum-macros/tests/debug_handler/fail/request_not_last.stderr
new file mode 100644
index 00000000..a3482e64
--- /dev/null
+++ b/axum-macros/tests/debug_handler/fail/request_not_last.stderr
@@ -0,0 +1,5 @@
+error: `Request` extractor should always be last
+ --> tests/debug_handler/fail/request_not_last.rs:5:18
+  |
+5 | async fn handler(_: Request<Body>, _: Extension<String>) {}
+  |                  ^^^^^^^^^^^^^^^^
diff --git a/axum-macros/tests/debug_handler/pass/request_last.rs b/axum-macros/tests/debug_handler/pass/request_last.rs
new file mode 100644
index 00000000..bbfb53d2
--- /dev/null
+++ b/axum-macros/tests/debug_handler/pass/request_last.rs
@@ -0,0 +1,7 @@
+use axum::{body::Body, extract::Extension, http::Request};
+use axum_macros::debug_handler;
+
+#[debug_handler]
+async fn handler(_: Extension<String>, _: Request<Body>) {}
+
+fn main() {}