diff --git a/src/config/mcp_factory.rs b/src/config/mcp_factory.rs
index 4a46a35..0afc715 100644
--- a/src/config/mcp_factory.rs
+++ b/src/config/mcp_factory.rs
@@ -1,7 +1,6 @@
-use crate::mcp::oauth::McpTokenStatus;
 use crate::mcp::{
-    ConnectedServer, JsonField, McpAuthReason, McpAuthRequired, McpServer, McpTransportType,
-    is_auth_required_error, oauth, spawn_mcp_server,
+    ConnectedServer, JsonField, McpAuthRequired, McpServer, McpTransportType,
+    is_auth_required_error, resolve_http_auth, spawn_mcp_server,
 };
 
 use anyhow::Result;
@@ -103,13 +102,8 @@ impl McpFactory {
             return Ok(existing);
         }
 
-        let token_status = if spec.is_remote() {
-            oauth::load_or_refresh_mcp_token(name).await
-        } else {
-            McpTokenStatus::NotAuthenticated
-        };
-        let auth_reason = McpAuthReason::from_token_status(&token_status);
-        let handle = spawn_mcp_server(spec, log_path, token_status.into_token())
+        let (auth, auth_reason) = resolve_http_auth(name, spec).await;
+        let handle = spawn_mcp_server(spec, log_path, auth)
             .await
             .map_err(|e| {
                 if is_auth_required_error(&e) {
diff --git a/src/mcp/auth_client.rs b/src/mcp/auth_client.rs
new file mode 100644
index 0000000..d337f23
--- /dev/null
+++ b/src/mcp/auth_client.rs
@@ -0,0 +1,651 @@
+use crate::mcp::oauth::{force_refresh_mcp_token, load_or_refresh_mcp_token};
+use http::{HeaderName, HeaderValue};
+use log::debug;
+use rmcp::model::ClientJsonRpcMessage;
+use rmcp::transport::common::client_side_sse::BoxedSseResponse;
+use rmcp::transport::streamable_http_client::{
+    AuthRequiredError, StreamableHttpClient, StreamableHttpError, StreamableHttpPostResponse,
+};
+use std::collections::HashMap;
+use std::future::Future;
+use std::sync::Arc;
+
+/// [`StreamableHttpClient`] wrapper that injects the OAuth bearer token for an
+/// MCP server on every request instead of pinning it at spawn time, so tokens
+/// refreshed mid-session take effect without reconnecting.
+///
+/// A caller-supplied `auth_header` always passes through untouched; only a
+/// `None` header is filled from the stored token. When the wrapper injected
+/// the token and a POST comes back 401, it forces a token refresh and retries
+/// exactly once (see [`Self::post_with_retry`]).
+#[derive(Clone)]
+pub struct McpOAuthClient<C = reqwest::Client> {
+    inner: C,
+    server: Arc<str>,
+}
+
+impl<C> McpOAuthClient<C> {
+    pub fn new(inner: C, server: &str) -> Self {
+        Self {
+            inner,
+            server: Arc::from(server),
+        }
+    }
+}
+
+impl<C: StreamableHttpClient + Sync> McpOAuthClient<C> {
+    /// Resolves the effective auth header. Caller-supplied values pass through
+    /// untouched; `None` is filled from the stored token for this server.
+    /// Returns the header plus whether the wrapper injected it. Errors with
+    /// [`StreamableHttpError::AuthRequired`] (without contacting the server)
+    /// when no usable token exists.
+    async fn resolve_auth(
+        &self,
+        auth_header: Option<String>,
+    ) -> Result<(Option<String>, bool), StreamableHttpError<C::Error>> {
+        if auth_header.is_some() {
+            return Ok((auth_header, false));
+        }
+        match load_or_refresh_mcp_token(&self.server).await.into_token() {
+            Some(token) => Ok((Some(token), true)),
+            None => Err(self.auth_required()),
+        }
+    }
+
+    fn auth_required(&self) -> StreamableHttpError<C::Error> {
+        StreamableHttpError::AuthRequired(AuthRequiredError::new(format!(
+            "no valid OAuth token for MCP server '{server}'; \
+             run `.mcp auth {server}` to re-authenticate",
+            server = self.server
+        )))
+    }
+
+    async fn post_with_retry<F, Fut>(
+        &self,
+        auth_header: Option<String>,
+        mut post: F,
+    ) -> Result<StreamableHttpPostResponse, StreamableHttpError<C::Error>>
+    where
+        F: FnMut(Option<String>) -> Fut,
+        Fut: Future<Output = Result<StreamableHttpPostResponse, StreamableHttpError<C::Error>>>,
+    {
+        let (auth, injected) = self.resolve_auth(auth_header).await?;
+        let (original, rejected) = match (post(auth.clone()).await, auth) {
+            (Err(err @ StreamableHttpError::AuthRequired(_)), Some(rejected)) if injected => {
+                (err, rejected)
+            }
+            (result, _) => return result,
+        };
+
+        debug!(
+            "MCP server '{}' rejected the injected token; forcing a refresh and retrying once",
+            self.server
+        );
+
+        let Some(token) = force_refresh_mcp_token(&self.server, &rejected).await else {
+            return Err(original);
+        };
+
+        match post(Some(token)).await {
+            Err(StreamableHttpError::AuthRequired(_)) => {
+                debug!(
+                    "Retry after forced token refresh was rejected again by MCP server '{}'",
+                    self.server
+                );
+                Err(original)
+            }
+            result => result,
+        }
+    }
+}
+
+impl<C: StreamableHttpClient + Sync> StreamableHttpClient for McpOAuthClient<C> {
+    type Error = C::Error;
+
+    async fn post_message(
+        &self,
+        uri: Arc<str>,
+        message: ClientJsonRpcMessage,
+        session_id: Option<Arc<str>>,
+        auth_header: Option<String>,
+        custom_headers: HashMap<HeaderName, HeaderValue>,
+    ) -> Result<StreamableHttpPostResponse, StreamableHttpError<Self::Error>> {
+        self.post_with_retry(auth_header, |auth| {
+            self.inner.post_message(
+                uri.clone(),
+                message.clone(),
+                session_id.clone(),
+                auth,
+                custom_headers.clone(),
+            )
+        })
+        .await
+    }
+
+    /// Overridden rather than left to the trait default: the default impl
+    /// delegates to [`Self::post_message`], silently dropping the
+    /// transport-wide SSE event size limit. Delegating to the inner client's
+    /// size-enforcing variant keeps the limit applied at the raw byte layer.
+    async fn post_message_with_max_sse_event_size(
+        &self,
+        uri: Arc<str>,
+        message: ClientJsonRpcMessage,
+        session_id: Option<Arc<str>>,
+        auth_header: Option<String>,
+        custom_headers: HashMap<HeaderName, HeaderValue>,
+        max_sse_event_size: usize,
+    ) -> Result<StreamableHttpPostResponse, StreamableHttpError<Self::Error>> {
+        self.post_with_retry(auth_header, |auth| {
+            self.inner.post_message_with_max_sse_event_size(
+                uri.clone(),
+                message.clone(),
+                session_id.clone(),
+                auth,
+                custom_headers.clone(),
+                max_sse_event_size,
+            )
+        })
+        .await
+    }
+
+    async fn delete_session(
+        &self,
+        uri: Arc<str>,
+        session_id: Arc<str>,
+        auth_header: Option<String>,
+        custom_headers: HashMap<HeaderName, HeaderValue>,
+    ) -> Result<(), StreamableHttpError<Self::Error>> {
+        let (auth, _) = self.resolve_auth(auth_header).await?;
+        self.inner
+            .delete_session(uri, session_id, auth, custom_headers)
+            .await
+    }
+
+    async fn get_stream(
+        &self,
+        uri: Arc<str>,
+        session_id: Option<Arc<str>>,
+        last_event_id: Option<String>,
+        auth_header: Option<String>,
+        custom_headers: HashMap<HeaderName, HeaderValue>,
+    ) -> Result<BoxedSseResponse, StreamableHttpError<Self::Error>> {
+        let (auth, _) = self.resolve_auth(auth_header).await?;
+        self.inner
+            .get_stream(uri, session_id, last_event_id, auth, custom_headers)
+            .await
+    }
+
+    /// Overridden for the same reason as
+    /// [`Self::post_message_with_max_sse_event_size`]: the trait default
+    /// bypasses SSE event size enforcement.
+    async fn get_stream_with_max_sse_event_size(
+        &self,
+        uri: Arc<str>,
+        session_id: Option<Arc<str>>,
+        last_event_id: Option<String>,
+        auth_header: Option<String>,
+        custom_headers: HashMap<HeaderName, HeaderValue>,
+        max_sse_event_size: usize,
+    ) -> Result<BoxedSseResponse, StreamableHttpError<Self::Error>> {
+        let (auth, _) = self.resolve_auth(auth_header).await?;
+        self.inner
+            .get_stream_with_max_sse_event_size(
+                uri,
+                session_id,
+                last_event_id,
+                auth,
+                custom_headers,
+                max_sse_event_size,
+            )
+            .await
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::config::paths;
+    use crate::mcp::oauth::test_support::with_temp_cache;
+    use futures_util::StreamExt;
+    use parking_lot::Mutex;
+    use serial_test::serial;
+    use std::convert::Infallible;
+    use std::fs;
+    use std::sync::atomic::{AtomicUsize, Ordering};
+
+    const FRESH: i64 = 9999999999;
+
+    type Calls = Arc<Mutex<Vec<(&'static str, Option<String>)>>>;
+
+    type AfterFirstCallAction = Option<Box<dyn FnOnce() + Send + 'static>>;
+
+    /// Inner client that records `(method, auth_header)` per call, rejects the
+    /// first `reject_times` POSTs/streams with `AuthRequired` (then the next
+    /// `transport_error_times` with a non-auth error), and runs an optional
+    /// side effect after the first call (to mutate token files between the
+    /// initial attempt and the retry).
+    #[derive(Clone, Default)]
+    struct FakeInner {
+        calls: Calls,
+        reject_times: Arc<AtomicUsize>,
+        transport_error_times: Arc<AtomicUsize>,
+        after_first_call: Arc<Mutex<AfterFirstCallAction>>,
+    }
+
+    impl FakeInner {
+        fn record(
+            &self,
+            method: &'static str,
+            auth: Option<String>,
+        ) -> Result<(), StreamableHttpError<Infallible>> {
+            self.calls.lock().push((method, auth));
+            if let Some(f) = self.after_first_call.lock().take() {
+                f();
+            }
+            if self.reject_times.load(Ordering::SeqCst) > 0 {
+                self.reject_times.fetch_sub(1, Ordering::SeqCst);
+                return Err(Self::rejection());
+            }
+            if self.transport_error_times.load(Ordering::SeqCst) > 0 {
+                self.transport_error_times.fetch_sub(1, Ordering::SeqCst);
+                return Err(StreamableHttpError::UnexpectedServerResponse(
+                    "connection reset".into(),
+                ));
+            }
+            Ok(())
+        }
+
+        fn rejection() -> StreamableHttpError<Infallible> {
+            StreamableHttpError::AuthRequired(AuthRequiredError::new(
+                "Bearer error=\"invalid_token\"".to_string(),
+            ))
+        }
+    }
+
+    impl StreamableHttpClient for FakeInner {
+        type Error = Infallible;
+
+        async fn post_message(
+            &self,
+            _uri: Arc<str>,
+            _message: ClientJsonRpcMessage,
+            _session_id: Option<Arc<str>>,
+            auth_header: Option<String>,
+            _custom_headers: HashMap<HeaderName, HeaderValue>,
+        ) -> Result<StreamableHttpPostResponse, StreamableHttpError<Self::Error>> {
+            self.record("post_message", auth_header)?;
+            Ok(StreamableHttpPostResponse::Accepted)
+        }
+
+        async fn post_message_with_max_sse_event_size(
+            &self,
+            _uri: Arc<str>,
+            _message: ClientJsonRpcMessage,
+            _session_id: Option<Arc<str>>,
+            auth_header: Option<String>,
+            _custom_headers: HashMap<HeaderName, HeaderValue>,
+            _max_sse_event_size: usize,
+        ) -> Result<StreamableHttpPostResponse, StreamableHttpError<Self::Error>> {
+            self.record("post_message_with_max_sse_event_size", auth_header)?;
+            Ok(StreamableHttpPostResponse::Accepted)
+        }
+
+        async fn delete_session(
+            &self,
+            _uri: Arc<str>,
+            _session_id: Arc<str>,
+            auth_header: Option<String>,
+            _custom_headers: HashMap<HeaderName, HeaderValue>,
+        ) -> Result<(), StreamableHttpError<Self::Error>> {
+            self.record("delete_session", auth_header)?;
+            Ok(())
+        }
+
+        async fn get_stream(
+            &self,
+            _uri: Arc<str>,
+            _session_id: Option<Arc<str>>,
+            _last_event_id: Option<String>,
+            auth_header: Option<String>,
+            _custom_headers: HashMap<HeaderName, HeaderValue>,
+        ) -> Result<BoxedSseResponse, StreamableHttpError<Self::Error>> {
+            self.record("get_stream", auth_header)?;
+            Ok(futures_util::stream::empty().boxed())
+        }
+
+        async fn get_stream_with_max_sse_event_size(
+            &self,
+            _uri: Arc<str>,
+            _session_id: Option<Arc<str>>,
+            _last_event_id: Option<String>,
+            auth_header: Option<String>,
+            _custom_headers: HashMap<HeaderName, HeaderValue>,
+            _max_sse_event_size: usize,
+        ) -> Result<BoxedSseResponse, StreamableHttpError<Self::Error>> {
+            self.record("get_stream_with_max_sse_event_size", auth_header)?;
+            Ok(futures_util::stream::empty().boxed())
+        }
+    }
+
+    fn write_token_file(server: &str, access_token: &str, expires_at: i64) {
+        fs::create_dir_all(paths::oauth_tokens_dir()).unwrap();
+        fs::write(
+            paths::token_file(&format!("mcp_{server}")),
+            format!(
+                r#"{{"access_token":"{access_token}","refresh_token":"r","expires_at":{expires_at}}}"#
+            ),
+        )
+        .unwrap();
+    }
+
+    fn ping() -> ClientJsonRpcMessage {
+        serde_json::from_value(serde_json::json!({
+            "jsonrpc": "2.0",
+            "id": 1,
+            "method": "ping"
+        }))
+        .unwrap()
+    }
+
+    fn rt() -> tokio::runtime::Runtime {
+        tokio::runtime::Builder::new_current_thread()
+            .enable_all()
+            .build()
+            .unwrap()
+    }
+
+    fn post(
+        client: &McpOAuthClient<FakeInner>,
+        auth_header: Option<String>,
+    ) -> Result<StreamableHttpPostResponse, StreamableHttpError<Infallible>> {
+        rt().block_on(client.post_message(
+            Arc::from("http://mcp.test/mcp"),
+            ping(),
+            None,
+            auth_header,
+            HashMap::new(),
+        ))
+    }
+
+    #[test]
+    #[serial]
+    fn injects_token_from_disk_when_auth_header_none() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-inject", "tok-live", FRESH);
+            let inner = FakeInner::default();
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-inject");
+
+            let result = post(&client, None);
+
+            assert!(result.is_ok());
+            assert_eq!(
+                *inner.calls.lock(),
+                vec![("post_message", Some("tok-live".to_string()))]
+            );
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn caller_supplied_auth_header_passes_through() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-passthrough", "tok-disk", FRESH);
+            let inner = FakeInner::default();
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-passthrough");
+
+            let result = post(&client, Some("caller-tok".to_string()));
+
+            assert!(result.is_ok());
+            assert_eq!(
+                *inner.calls.lock(),
+                vec![("post_message", Some("caller-tok".to_string()))]
+            );
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn caller_supplied_header_rejection_propagates_without_refresh() {
+        with_temp_cache(|| {
+            // A fresh, different token sits on disk: if the injected guard
+            // were dropped, the wrapper would refresh and retry with it.
+            write_token_file("wrapper-caller-401", "tok-disk", FRESH);
+            let inner = FakeInner::default();
+            inner.reject_times.store(1, Ordering::SeqCst);
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-caller-401");
+
+            let result = post(&client, Some("caller-tok".to_string()));
+
+            assert!(matches!(result, Err(StreamableHttpError::AuthRequired(_))));
+            assert_eq!(
+                *inner.calls.lock(),
+                vec![("post_message", Some("caller-tok".to_string()))]
+            );
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn missing_token_returns_auth_required_without_calling_inner() {
+        with_temp_cache(|| {
+            let inner = FakeInner::default();
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-no-token");
+
+            let result = post(&client, None);
+
+            assert!(matches!(result, Err(StreamableHttpError::AuthRequired(_))));
+            assert!(inner.calls.lock().is_empty());
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn rejected_token_forces_refresh_and_retries_once() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-retry", "tok-a", FRESH);
+            let inner = FakeInner::default();
+            inner.reject_times.store(1, Ordering::SeqCst);
+            // Simulate a concurrent refresh landing between the rejection and
+            // the forced refresh: the retry must carry the new token.
+            *inner.after_first_call.lock() = Some(Box::new(|| {
+                write_token_file("wrapper-retry", "tok-b", FRESH);
+            }));
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-retry");
+
+            let result = post(&client, None);
+
+            assert!(result.is_ok());
+            assert_eq!(
+                *inner.calls.lock(),
+                vec![
+                    ("post_message", Some("tok-a".to_string())),
+                    ("post_message", Some("tok-b".to_string())),
+                ]
+            );
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn failed_force_refresh_propagates_original_error_after_one_call() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-refresh-fail", "tok-a", FRESH);
+            let inner = FakeInner::default();
+            inner.reject_times.store(1, Ordering::SeqCst);
+            // Token file gone by refresh time: force refresh yields nothing.
+            *inner.after_first_call.lock() = Some(Box::new(|| {
+                fs::remove_file(paths::token_file("mcp_wrapper-refresh-fail")).unwrap();
+            }));
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-refresh-fail");
+
+            let result = post(&client, None);
+
+            assert!(matches!(result, Err(StreamableHttpError::AuthRequired(_))));
+            assert_eq!(inner.calls.lock().len(), 1);
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn second_rejection_after_retry_propagates_original_error() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-double-401", "tok-a", FRESH);
+            let inner = FakeInner::default();
+            inner.reject_times.store(2, Ordering::SeqCst);
+            // A changed token appears before the forced refresh, so the retry
+            // actually runs (an unchanged token would trigger a real refresh
+            // attempt, which fails without a cached registration).
+            *inner.after_first_call.lock() = Some(Box::new(|| {
+                write_token_file("wrapper-double-401", "tok-b", FRESH);
+            }));
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-double-401");
+
+            let result = post(&client, None);
+
+            assert!(matches!(result, Err(StreamableHttpError::AuthRequired(_))));
+            assert_eq!(inner.calls.lock().len(), 2);
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn non_auth_retry_error_propagates_as_is() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-retry-transport", "tok-a", FRESH);
+            let inner = FakeInner::default();
+            inner.reject_times.store(1, Ordering::SeqCst);
+            inner.transport_error_times.store(1, Ordering::SeqCst);
+            *inner.after_first_call.lock() = Some(Box::new(|| {
+                write_token_file("wrapper-retry-transport", "tok-b", FRESH);
+            }));
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-retry-transport");
+
+            let result = post(&client, None);
+
+            assert!(matches!(
+                result,
+                Err(StreamableHttpError::UnexpectedServerResponse(_))
+            ));
+            assert_eq!(inner.calls.lock().len(), 2);
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn sized_post_delegates_to_inner_sized_variant() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-sized-post", "tok-live", FRESH);
+            let inner = FakeInner::default();
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-sized-post");
+
+            let result = rt().block_on(client.post_message_with_max_sse_event_size(
+                Arc::from("http://mcp.test/mcp"),
+                ping(),
+                None,
+                None,
+                HashMap::new(),
+                4096,
+            ));
+
+            assert!(result.is_ok());
+            assert_eq!(
+                *inner.calls.lock(),
+                vec![(
+                    "post_message_with_max_sse_event_size",
+                    Some("tok-live".to_string())
+                )]
+            );
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn sized_get_stream_delegates_to_inner_sized_variant() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-sized-get", "tok-live", FRESH);
+            let inner = FakeInner::default();
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-sized-get");
+
+            let result = rt().block_on(client.get_stream_with_max_sse_event_size(
+                Arc::from("http://mcp.test/mcp"),
+                None,
+                None,
+                None,
+                HashMap::new(),
+                4096,
+            ));
+
+            assert!(result.is_ok());
+            assert_eq!(
+                *inner.calls.lock(),
+                vec![(
+                    "get_stream_with_max_sse_event_size",
+                    Some("tok-live".to_string())
+                )]
+            );
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn get_stream_does_not_retry_on_rejection() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-get-401", "tok-live", FRESH);
+            let inner = FakeInner::default();
+            inner.reject_times.store(1, Ordering::SeqCst);
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-get-401");
+
+            let result = rt().block_on(client.get_stream(
+                Arc::from("http://mcp.test/mcp"),
+                None,
+                None,
+                None,
+                HashMap::new(),
+            ));
+
+            assert!(matches!(result, Err(StreamableHttpError::AuthRequired(_))));
+            assert_eq!(inner.calls.lock().len(), 1);
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn delete_session_injects_token() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-delete", "tok-live", FRESH);
+            let inner = FakeInner::default();
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-delete");
+
+            let result = rt().block_on(client.delete_session(
+                Arc::from("http://mcp.test/mcp"),
+                Arc::from("session-1"),
+                None,
+                HashMap::new(),
+            ));
+
+            assert!(result.is_ok());
+            assert_eq!(
+                *inner.calls.lock(),
+                vec![("delete_session", Some("tok-live".to_string()))]
+            );
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn auth_required_error_contains_no_token_material() {
+        with_temp_cache(|| {
+            write_token_file("wrapper-redact", "stale-secret-token", 0);
+            let inner = FakeInner::default();
+            let client = McpOAuthClient::new(inner.clone(), "wrapper-redact");
+
+            let err = post(&client, None).unwrap_err();
+
+            let display = format!("{err}");
+            let debug = format!("{err:?}");
+            assert!(!display.contains("stale-secret-token"));
+            assert!(!debug.contains("stale-secret-token"));
+            assert!(inner.calls.lock().is_empty());
+        });
+    }
+}
diff --git a/src/mcp/mod.rs b/src/mcp/mod.rs
index 4b8baf4..e6b6222 100644
--- a/src/mcp/mod.rs
+++ b/src/mcp/mod.rs
@@ -1,3 +1,4 @@
+mod auth_client;
 pub(crate) mod manage;
 pub(crate) mod oauth;
 mod sse_transport;
@@ -9,6 +10,7 @@ use crate::vault::Vault;
 use crate::vault::interpolate_secrets;
 use anyhow::Error;
 use anyhow::{Context, Result, anyhow};
+use auth_client::McpOAuthClient;
 use futures_util::{StreamExt, TryStreamExt, stream};
 use http::{HeaderName, HeaderValue};
 use indexmap::IndexMap;
@@ -328,29 +330,22 @@ impl McpRegistry {
             .and_then(|c| c.mcp_servers.get(&id))
             .with_context(|| format!("MCP server not found in config: {id}"))?;
 
-        let token_status = if spec.is_remote() {
-            oauth::load_or_refresh_mcp_token(&id).await
-        } else {
-            oauth::McpTokenStatus::NotAuthenticated
-        };
-        let auth_reason = McpAuthReason::from_token_status(&token_status);
+        let (auth, auth_reason) = resolve_http_auth(&id, spec).await;
 
-        let service =
-            match spawn_mcp_server(spec, self.log_path.as_deref(), token_status.into_token()).await
-            {
-                Ok(s) => s,
-                Err(e) if is_auth_required_error(&e) => {
-                    warn!(
-                        "{}",
-                        McpAuthRequired {
-                            server: id,
-                            reason: auth_reason,
-                        }
-                    );
-                    return Ok(None);
-                }
-                Err(e) => return Err(e),
-            };
+        let service = match spawn_mcp_server(spec, self.log_path.as_deref(), auth).await {
+            Ok(s) => s,
+            Err(e) if is_auth_required_error(&e) => {
+                warn!(
+                    "{}",
+                    McpAuthRequired {
+                        server: id,
+                        reason: auth_reason,
+                    }
+                );
+                return Ok(None);
+            }
+            Err(e) => return Err(e),
+        };
 
         let tools = service.list_tools(None).await?;
         debug!("Available tools for MCP server {id}: {tools:?}");
@@ -420,19 +415,76 @@ impl McpRegistry {
     }
 }
 
+/// How a remote MCP server authenticates outgoing requests.
+pub(crate) enum HttpAuth {
+    /// Only the static headers from the server spec; no OAuth token.
+    StaticOnly,
+    /// OAuth-managed: HTTP transports inject a fresh bearer token per request
+    /// via [`McpOAuthClient`] (ignoring the carried token); SSE transports
+    /// send the carried token as a static header.
+    Managed { server: String, token: String },
+}
+
+impl fmt::Debug for HttpAuth {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match self {
+            Self::StaticOnly => f.write_str("StaticOnly"),
+            Self::Managed { server, token: _ } => f
+                .debug_struct("Managed")
+                .field("server", server)
+                .field("token", &"<redacted>")
+                .finish(),
+        }
+    }
+}
+
+impl HttpAuth {
+    pub(crate) fn from_token_status(status: &oauth::McpTokenStatus, server: &str) -> Self {
+        match status {
+            oauth::McpTokenStatus::Token(token) => Self::Managed {
+                server: server.to_string(),
+                token: token.clone(),
+            },
+            oauth::McpTokenStatus::NotAuthenticated | oauth::McpTokenStatus::RefreshFailed => {
+                Self::StaticOnly
+            }
+        }
+    }
+}
+
+pub(crate) async fn resolve_http_auth(name: &str, spec: &McpServer) -> (HttpAuth, McpAuthReason) {
+    let token_status = if spec.is_remote() {
+        oauth::load_or_refresh_mcp_token(name).await
+    } else {
+        oauth::McpTokenStatus::NotAuthenticated
+    };
+    (
+        HttpAuth::from_token_status(&token_status, name),
+        McpAuthReason::from_token_status(&token_status),
+    )
+}
+
 pub(crate) async fn spawn_mcp_server(
     spec: &McpServer,
     log_path: Option<&Path>,
-    bearer_token: Option<String>,
+    auth: HttpAuth,
 ) -> Result<Arc<ConnectedServer>> {
     match spec.transport_type {
         McpTransportType::Http => {
             let url = spec.url.as_deref().expect("validated: http spec has url");
-            let headers = merge_bearer_token(spec.headers.as_ref(), bearer_token);
-            spawn_http_mcp_server(url, headers.as_ref()).await
+            match auth {
+                HttpAuth::Managed { server, token: _ } => {
+                    spawn_oauth_http_mcp_server(url, &server, spec.headers.as_ref()).await
+                }
+                HttpAuth::StaticOnly => spawn_http_mcp_server(url, spec.headers.as_ref()).await,
+            }
         }
         McpTransportType::Sse => {
             let url = spec.url.as_deref().expect("validated: sse spec has url");
+            let bearer_token = match auth {
+                HttpAuth::Managed { server: _, token } => Some(token),
+                HttpAuth::StaticOnly => None,
+            };
             let headers = merge_bearer_token(spec.headers.as_ref(), bearer_token);
             spawn_sse_mcp_server(url, headers.as_ref()).await
         }
@@ -460,6 +512,7 @@ fn merge_bearer_token(
         }
         (Some(h), Some(token)) => {
             let mut m = h.clone();
+            m.retain(|k, _| !k.eq_ignore_ascii_case("authorization"));
             m.insert("Authorization".to_string(), format!("Bearer {token}"));
             Some(m)
         }
@@ -551,6 +604,66 @@ async fn spawn_http_mcp_server(
     Ok(service)
 }
 
+/// Builds the custom-header map for an OAuth-managed HTTP transport, dropping
+/// any static `Authorization` entry case-insensitively: [`McpOAuthClient`]
+/// owns that header, and a stale configured value must not collide with the
+/// per-request token.
+fn oauth_custom_headers(
+    headers: Option<&IndexMap<String, String>>,
+) -> Result<HashMap<HeaderName, HeaderValue>> {
+    let mut custom = HashMap::new();
+    let Some(hdrs) = headers else {
+        return Ok(custom);
+    };
+
+    for (k, v) in hdrs {
+        if k.eq_ignore_ascii_case("authorization") {
+            continue;
+        }
+        let name = k
+            .parse::<HeaderName>()
+            .with_context(|| format!("Invalid header name: {k}"))?;
+        let value = v
+            .parse::<HeaderValue>()
+            .with_context(|| format!("Invalid header value for {k}"))?;
+        custom.insert(name, value);
+    }
+
+    Ok(custom)
+}
+
+async fn spawn_oauth_http_mcp_server(
+    url: &str,
+    server: &str,
+    headers: Option<&IndexMap<String, String>>,
+) -> Result<Arc<ConnectedServer>> {
+    // Mirror rmcp's default_http_client, which `with_client` bypasses:
+    // idle pooling off avoids a documented TCP delayed-ACK stall, and
+    // redirects off keeps custom headers from being replayed to a redirect
+    // target.
+    let inner = reqwest::Client::builder()
+        .pool_max_idle_per_host(0)
+        .redirect(reqwest::redirect::Policy::none())
+        .build()
+        .context("Failed to build HTTP client for OAuth-managed MCP transport")?;
+    let client = McpOAuthClient::new(inner, server);
+    // `auth_header` stays None so the wrapper injects a fresh token per
+    // request; `reinit_on_expired_session` defaults to true in rmcp 3.1.2
+    // but is pinned explicitly because transparent session re-init is
+    // load-bearing for long-lived sessions.
+    let config = StreamableHttpClientTransportConfig::with_uri(url)
+        .custom_headers(oauth_custom_headers(headers)?)
+        .reinit_on_expired_session(true);
+    let transport = StreamableHttpClientTransport::with_client(client, config);
+    let service = Arc::new(
+        ().serve(transport)
+            .await
+            .with_context(|| format!("Failed to connect to HTTP MCP server: {url}"))?,
+    );
+
+    Ok(service)
+}
+
 async fn spawn_sse_mcp_server(
     url: &str,
     headers: Option<&IndexMap<String, String>>,
@@ -1109,6 +1222,92 @@ mod tests {
         assert_eq!(result["X-Custom"], "keep");
     }
 
+    #[test]
+    fn merge_bearer_token_replaces_authorization_case_insensitively() {
+        let mut h = IndexMap::new();
+        h.insert("authorization".to_string(), "Bearer stale-1".to_string());
+        h.insert("AUTHORIZATION".to_string(), "Bearer stale-2".to_string());
+        h.insert("X-Custom".to_string(), "keep".to_string());
+
+        let result = merge_bearer_token(Some(&h), Some("newtoken".to_string())).unwrap();
+
+        assert_eq!(result.len(), 2);
+        assert_eq!(result["Authorization"], "Bearer newtoken");
+        assert_eq!(result["X-Custom"], "keep");
+        assert!(!result.contains_key("authorization"));
+        assert!(!result.contains_key("AUTHORIZATION"));
+    }
+
+    #[test]
+    fn http_auth_from_token_status_maps_token_to_managed() {
+        assert!(matches!(
+            HttpAuth::from_token_status(&oauth::McpTokenStatus::Token("tok".into()), "srv"),
+            HttpAuth::Managed { server, token } if server == "srv" && token == "tok"
+        ));
+        assert!(matches!(
+            HttpAuth::from_token_status(&oauth::McpTokenStatus::NotAuthenticated, "srv"),
+            HttpAuth::StaticOnly
+        ));
+        assert!(matches!(
+            HttpAuth::from_token_status(&oauth::McpTokenStatus::RefreshFailed, "srv"),
+            HttpAuth::StaticOnly
+        ));
+    }
+
+    #[test]
+    fn http_auth_debug_redacts_token() {
+        let auth = HttpAuth::Managed {
+            server: "srv".into(),
+            token: "live-secret".into(),
+        };
+
+        let debug = format!("{auth:?}");
+
+        assert!(debug.contains("srv"));
+        assert!(debug.contains("<redacted>"));
+        assert!(!debug.contains("live-secret"));
+    }
+
+    #[test]
+    fn oauth_custom_headers_strips_authorization_case_insensitively() {
+        let mut h = IndexMap::new();
+        h.insert("Authorization".to_string(), "Bearer stale-1".to_string());
+        h.insert("authorization".to_string(), "Bearer stale-2".to_string());
+        h.insert("AUTHORIZATION".to_string(), "Bearer stale-3".to_string());
+        h.insert("X-Custom".to_string(), "keep".to_string());
+
+        let custom = oauth_custom_headers(Some(&h)).unwrap();
+
+        assert_eq!(custom.len(), 1);
+        assert_eq!(custom[&HeaderName::from_static("x-custom")], "keep");
+    }
+
+    #[test]
+    fn oauth_custom_headers_none_is_empty() {
+        assert!(oauth_custom_headers(None).unwrap().is_empty());
+    }
+
+    #[test]
+    fn oauth_custom_headers_rejects_invalid_header_name() {
+        let mut h = IndexMap::new();
+        h.insert("bad header".to_string(), "v".to_string());
+
+        assert!(oauth_custom_headers(Some(&h)).is_err());
+    }
+
+    #[test]
+    fn oauth_custom_headers_keeps_non_authorization_headers() {
+        let mut h = IndexMap::new();
+        h.insert("X-Api-Key".to_string(), "k".to_string());
+        h.insert("X-Trace".to_string(), "t".to_string());
+
+        let custom = oauth_custom_headers(Some(&h)).unwrap();
+
+        assert_eq!(custom.len(), 2);
+        assert_eq!(custom[&HeaderName::from_static("x-api-key")], "k");
+        assert_eq!(custom[&HeaderName::from_static("x-trace")], "t");
+    }
+
     #[test]
     fn is_auth_required_error_matches_rmcp_message() {
         let e = anyhow!("Auth required, when send initialize request");
diff --git a/src/mcp/oauth.rs b/src/mcp/oauth.rs
index bd2f89e..a911f36 100644
--- a/src/mcp/oauth.rs
+++ b/src/mcp/oauth.rs
@@ -10,6 +10,7 @@ use log::{debug, warn};
 use reqwest::Client;
 use serde::{Deserialize, Serialize};
 use std::collections::HashMap;
+use std::fmt;
 use std::fs;
 use std::net::TcpListener;
 use std::sync::{Arc, OnceLock};
@@ -202,13 +203,23 @@ pub async fn run_mcp_oauth_flow(
     run_oauth_flow(&provider, &mcp_token_key(server_name)).await
 }
 
-#[derive(Debug, PartialEq, Eq)]
+#[derive(PartialEq, Eq)]
 pub enum McpTokenStatus {
     Token(String),
     NotAuthenticated,
     RefreshFailed,
 }
 
+impl fmt::Debug for McpTokenStatus {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match self {
+            Self::Token(_) => f.write_str("Token(<redacted>)"),
+            Self::NotAuthenticated => f.write_str("NotAuthenticated"),
+            Self::RefreshFailed => f.write_str("RefreshFailed"),
+        }
+    }
+}
+
 impl McpTokenStatus {
     pub fn into_token(self) -> Option<String> {
         match self {
@@ -219,11 +230,28 @@ impl McpTokenStatus {
 }
 
 pub async fn load_or_refresh_mcp_token(server_name: &str) -> McpTokenStatus {
+    load_or_refresh_inner(server_name, None).await
+}
+
+/// Re-acquires a token after the server rejected the current one mid-session
+/// (HTTP 401). The rejection proves the stored token is bad regardless of its
+/// expiry timestamp, so the unexpired fast-paths only short-circuit when the
+/// stored token DIFFERS from `rejected_token` (a concurrent caller genuinely
+/// refreshed while we waited); an unexpired copy of the rejected token is
+/// refreshed anyway. The failure backoff and per-server single-flight lock
+/// still apply.
+pub async fn force_refresh_mcp_token(server_name: &str, rejected_token: &str) -> Option<String> {
+    load_or_refresh_inner(server_name, Some(rejected_token))
+        .await
+        .into_token()
+}
+
+async fn load_or_refresh_inner(server_name: &str, rejected_token: Option<&str>) -> McpTokenStatus {
     let key = mcp_token_key(server_name);
     let Some(tokens) = load_oauth_tokens(&key) else {
         return McpTokenStatus::NotAuthenticated;
     };
-    if Utc::now().timestamp() < tokens.expires_at {
+    if rejected_token.is_none() && Utc::now().timestamp() < tokens.expires_at {
         return McpTokenStatus::Token(tokens.access_token);
     }
 
@@ -235,11 +263,15 @@ pub async fn load_or_refresh_mcp_token(server_name: &str) -> McpTokenStatus {
     let lock = refresh_lock(server_name);
     let _guard = lock.lock().await;
 
-    // A concurrent caller may have refreshed while we waited for the lock.
+    // A concurrent caller may have refreshed while we waited for the lock. An
+    // unexpired token is only trusted if it differs from the rejected one:
+    // the server already proved that exact token bad.
     let Some(tokens) = load_oauth_tokens(&key) else {
         return McpTokenStatus::NotAuthenticated;
     };
-    if Utc::now().timestamp() < tokens.expires_at {
+    if Utc::now().timestamp() < tokens.expires_at
+        && rejected_token.is_none_or(|rejected| rejected != tokens.access_token)
+    {
         return McpTokenStatus::Token(tokens.access_token);
     }
 
@@ -589,10 +621,8 @@ fn extract_base_url(url: &str) -> Result<String> {
 }
 
 #[cfg(test)]
-mod tests {
-    use super::*;
+pub(crate) mod test_support {
     use crate::utils::get_env_name;
-    use serial_test::serial;
     use std::{
         env,
         ffi::OsString,
@@ -601,7 +631,7 @@ mod tests {
         time::{self, SystemTime},
     };
 
-    fn with_temp_cache<F: FnOnce()>(f: F) {
+    pub(crate) fn with_temp_cache<F: FnOnce()>(f: F) {
         struct Restore {
             key: String,
             prev: Option<OsString>,
@@ -637,6 +667,14 @@ mod tests {
         };
         f();
     }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::test_support::with_temp_cache;
+    use super::*;
+    use serial_test::serial;
+    use std::fs;
 
     #[test]
     fn extract_base_url_strips_path_and_query() {
@@ -1034,6 +1072,151 @@ mod tests {
         });
     }
 
+    #[test]
+    #[serial]
+    fn force_refresh_returns_concurrently_refreshed_token() {
+        with_temp_cache(|| {
+            fs::create_dir_all(paths::oauth_tokens_dir()).unwrap();
+            fs::write(
+                paths::token_file("mcp_force-fresh"),
+                r#"{"access_token":"fresh-tok","refresh_token":"r","expires_at":9999999999}"#,
+            )
+            .unwrap();
+
+            let rt = tokio::runtime::Builder::new_current_thread()
+                .enable_all()
+                .build()
+                .unwrap();
+            let token = rt.block_on(force_refresh_mcp_token("force-fresh", "rejected-tok"));
+
+            assert_eq!(token.as_deref(), Some("fresh-tok"));
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn force_refresh_unexpired_rejected_token_attempts_real_refresh() {
+        with_temp_cache(|| {
+            fs::create_dir_all(paths::oauth_tokens_dir()).unwrap();
+            fs::write(
+                paths::token_file("mcp_force-rejected"),
+                r#"{"access_token":"same-tok","refresh_token":"r","expires_at":9999999999}"#,
+            )
+            .unwrap();
+
+            let rt = tokio::runtime::Builder::new_current_thread()
+                .enable_all()
+                .build()
+                .unwrap();
+            let token = rt.block_on(force_refresh_mcp_token("force-rejected", "same-tok"));
+
+            assert_eq!(token, None);
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn force_refresh_missing_token_file_returns_none() {
+        with_temp_cache(|| {
+            let rt = tokio::runtime::Builder::new_current_thread()
+                .enable_all()
+                .build()
+                .unwrap();
+            let token = rt.block_on(force_refresh_mcp_token(
+                "force-never-authed",
+                "rejected-tok",
+            ));
+
+            assert_eq!(token, None);
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn force_refresh_failed_refresh_returns_none() {
+        with_temp_cache(|| {
+            fs::create_dir_all(paths::oauth_tokens_dir()).unwrap();
+            fs::write(
+                paths::token_file("mcp_force-fail"),
+                r#"{"access_token":"stale","refresh_token":"r","expires_at":0}"#,
+            )
+            .unwrap();
+
+            let rt = tokio::runtime::Builder::new_current_thread()
+                .enable_all()
+                .build()
+                .unwrap();
+            let token = rt.block_on(force_refresh_mcp_token("force-fail", "stale"));
+
+            assert_eq!(token, None);
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn force_refresh_concurrent_callers_complete_without_deadlock() {
+        with_temp_cache(|| {
+            fs::create_dir_all(paths::oauth_tokens_dir()).unwrap();
+            fs::write(
+                paths::token_file("mcp_force-concurrent"),
+                r#"{"access_token":"same-tok","refresh_token":"r","expires_at":9999999999}"#,
+            )
+            .unwrap();
+
+            let rt = tokio::runtime::Builder::new_current_thread()
+                .enable_all()
+                .build()
+                .unwrap();
+            let (a, b) = rt.block_on(async {
+                tokio::join!(
+                    force_refresh_mcp_token("force-concurrent", "same-tok"),
+                    force_refresh_mcp_token("force-concurrent", "same-tok"),
+                )
+            });
+
+            assert_eq!(a, None);
+            assert_eq!(b, None);
+        });
+    }
+
+    #[test]
+    #[serial]
+    fn force_refresh_respects_failure_backoff() {
+        with_temp_cache(|| {
+            fs::create_dir_all(paths::oauth_tokens_dir()).unwrap();
+            fs::write(
+                paths::token_file("mcp_force-backoff"),
+                r#"{"access_token":"same-tok","refresh_token":"r","expires_at":9999999999}"#,
+            )
+            .unwrap();
+            note_refresh_failure("force-backoff");
+
+            let rt = tokio::runtime::Builder::new_current_thread()
+                .enable_all()
+                .build()
+                .unwrap();
+            let token = rt.block_on(force_refresh_mcp_token("force-backoff", "same-tok"));
+
+            assert_eq!(token, None);
+        });
+    }
+
+    #[test]
+    fn token_status_debug_redacts_token() {
+        assert_eq!(
+            format!("{:?}", McpTokenStatus::Token("live-secret".into())),
+            "Token(<redacted>)"
+        );
+        assert_eq!(
+            format!("{:?}", McpTokenStatus::NotAuthenticated),
+            "NotAuthenticated"
+        );
+        assert_eq!(
+            format!("{:?}", McpTokenStatus::RefreshFailed),
+            "RefreshFailed"
+        );
+    }
+
     #[test]
     fn token_status_into_token_extracts_only_token_variant() {
         assert_eq!(