diff --git a/crates/nefarious-login/src/axum.rs b/crates/nefarious-login/src/axum.rs
index 424f067..1247cd3 100644
--- a/crates/nefarious-login/src/axum.rs
+++ b/crates/nefarious-login/src/axum.rs
@@ -2,8 +2,8 @@ use std::fmt::Display;
 
 use axum::extract::{FromRef, FromRequestParts, Query, State};
 use axum::http::request::Parts;
-use axum::http::StatusCode;
-use axum::response::{ErrorResponse, IntoResponse, Redirect};
+use axum::http::{HeaderMap, StatusCode, Uri};
+use axum::response::{ErrorResponse, IntoResponse, Redirect, Response};
 use axum::routing::get;
 use axum::{async_trait, Json, RequestPartsExt, Router};
 
@@ -97,13 +97,21 @@ pub struct UserFromSession {
 
 pub static COOKIE_NAME: &str = "SESSION";
 
+pub struct AuthRedirect((HeaderMap, String));
+
+impl IntoResponse for AuthRedirect {
+    fn into_response(self) -> Response {
+        (self.0 .0, Redirect::temporary(&self.0 .1.as_str())).into_response()
+    }
+}
+
 #[async_trait]
 impl<S> FromRequestParts<S> for UserFromSession
 where
     AuthService: FromRef<S>,
     S: Send + Sync,
 {
-    type Rejection = (StatusCode, &'static str);
+    type Rejection = AuthRedirect;
 
     async fn from_request_parts(parts: &mut Parts, state: &S) -> Result<Self, Self::Rejection> {
         let auth_service = AuthService::from_ref(state);
@@ -114,16 +122,21 @@ where
             let basic: Option<TypedHeader<Authorization<Basic>>> = parts.extract().await.unwrap();
 
             if let Some(basic) = basic {
-                let token = auth_service
+                let token = match auth_service
                     .login_token(basic.username(), basic.password())
                     .await
                     .into_response()
-                    .map_err(|_| {
-                        (
-                            StatusCode::INTERNAL_SERVER_ERROR,
-                            "could not get token from basic",
-                        )
-                    })?;
+                {
+                    Ok(login) => login,
+                    Err(e) => {
+                        tracing::info!("did not find a basic login token, will trigger login");
+                        let (headers, url) = auth_service
+                            .login(Some(parts.uri.to_string()))
+                            .await
+                            .expect("to be able to request login");
+                        return Err(AuthRedirect((headers, url.to_string())));
+                    }
+                };
 
                 return Ok(UserFromSession {
                     user: User {
@@ -134,24 +147,32 @@ where
                 });
             }
 
-            return Err(anyhow::anyhow!("No session was found"))
-                .into_response()
-                .map_err(|_| (StatusCode::INTERNAL_SERVER_ERROR, "did not find a cookie"))?;
+            tracing::info!("did not find a cookie, will trigger login");
+            let (headers, url) = auth_service
+                .login(Some(parts.uri.to_string()))
+                .await
+                .expect("to be able to request login");
+            return Err(AuthRedirect((headers, url.to_string())));
         }
 
         let session_cookie = session_cookie.unwrap();
 
         // continue to decode the session cookie
-        let user = auth_service
+        let user = match auth_service
             .get_user_from_session(session_cookie)
             .await
             .into_response()
-            .map_err(|_| {
-                (
-                    StatusCode::INTERNAL_SERVER_ERROR,
-                    "failed to decode session cookie",
-                )
-            })?;
+        {
+            Ok(user) => user,
+            Err(_) => {
+                tracing::info!("could not get user from session, will trigger login");
+                let (headers, url) = auth_service
+                    .login(Some(parts.uri.to_string()))
+                    .await
+                    .expect("to be able to request login");
+                return Err(AuthRedirect((headers, url.to_string())));
+            }
+        };
 
         Ok(UserFromSession { user })
     }