7 files changed, 305 insertions, 130 deletions

diff --git a/ext/http/http_next.rs b/ext/http/http_next.rs
index 7a6cbfa45..56c46de92 100644
--- a/ext/http/http_next.rs
+++ b/ext/http/http_next.rs
@@ -19,7 +19,6 @@ use crate::service::SignallingRc;
 use crate::websocket_upgrade::WebSocketUpgrade;
 use crate::LocalExecutor;
 use cache_control::CacheControl;
-use deno_core::error::AnyError;
 use deno_core::external;
 use deno_core::futures::future::poll_fn;
 use deno_core::futures::TryFutureExt;
@@ -146,12 +145,32 @@ macro_rules! clone_external {
   }};
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpNextError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(#[from] io::Error),
+  #[error(transparent)]
+  WebSocketUpgrade(crate::websocket_upgrade::WebSocketUpgradeError),
+  #[error("{0}")]
+  Hyper(#[from] hyper::Error),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error(transparent)]
+  HttpPropertyExtractor(deno_core::error::AnyError),
+  #[error(transparent)]
+  UpgradeUnavailable(#[from] crate::service::UpgradeUnavailableError),
+}
+
 #[op2(fast)]
 #[smi]
 pub fn op_http_upgrade_raw(
   state: &mut OpState,
   external: *const c_void,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpNextError> {
   // SAFETY: external is deleted before calling this op.
   let http = unsafe { take_external!(external, "op_http_upgrade_raw") };
 
@@ -177,7 +196,7 @@ pub fn op_http_upgrade_raw(
           upgraded.write_all(&bytes).await?;
           break upgraded;
         }
-        Err(err) => return Err(err),
+        Err(err) => return Err(HttpNextError::WebSocketUpgrade(err)),
       }
     };
 
@@ -193,7 +212,7 @@ pub fn op_http_upgrade_raw(
         }
         read_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, HttpNextError>(())
     });
     spawn(async move {
       let mut buf = [0; 1024];
@@ -204,7 +223,7 @@ pub fn op_http_upgrade_raw(
         }
         upgraded_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, HttpNextError>(())
     });
 
     Ok(())
@@ -223,7 +242,7 @@ pub async fn op_http_upgrade_websocket_next(
   state: Rc<RefCell<OpState>>,
   external: *const c_void,
   #[serde] headers: Vec<(ByteString, ByteString)>,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpNextError> {
   let http =
     // SAFETY: external is deleted before calling this op.
     unsafe { take_external!(external, "op_http_upgrade_websocket_next") };
@@ -690,7 +709,7 @@ pub async fn op_http_set_response_body_resource(
   #[smi] stream_rid: ResourceId,
   auto_close: bool,
   status: u16,
-) -> Result<bool, AnyError> {
+) -> Result<bool, HttpNextError> {
   let http =
     // SAFETY: op is called with external.
     unsafe { clone_external!(external, "op_http_set_response_body_resource") };
@@ -705,9 +724,15 @@ pub async fn op_http_set_response_body_resource(
   let resource = {
     let mut state = state.borrow_mut();
     if auto_close {
-      state.resource_table.take_any(stream_rid)?
+      state
+        .resource_table
+        .take_any(stream_rid)
+        .map_err(HttpNextError::Resource)?
     } else {
-      state.resource_table.get_any(stream_rid)?
+      state
+        .resource_table
+        .get_any(stream_rid)
+        .map_err(HttpNextError::Resource)?
     }
   };
 
@@ -814,17 +839,17 @@ async fn serve_http2_autodetect(
   io: impl HttpServeStream,
   svc: impl HttpService<Incoming, ResBody = HttpRecordResponse> + 'static,
   cancel: Rc<CancelHandle>,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpNextError> {
   let prefix = NetworkStreamPrefixCheck::new(io, HTTP2_PREFIX);
   let (matches, io) = prefix.match_prefix().await?;
   if matches {
     serve_http2_unconditional(io, svc, cancel)
       .await
-      .map_err(|e| e.into())
+      .map_err(HttpNextError::Hyper)
   } else {
     serve_http11_unconditional(io, svc, cancel)
       .await
-      .map_err(|e| e.into())
+      .map_err(HttpNextError::Hyper)
   }
 }
 
@@ -833,7 +858,7 @@ fn serve_https(
   request_info: HttpConnectionProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>> {
+) -> JoinHandle<Result<(), HttpNextError>> {
   let HttpLifetime {
     server_state,
     connection_cancel_handle,
@@ -852,11 +877,11 @@ fn serve_https(
       if Some(TLS_ALPN_HTTP_2) == handshake.as_deref() {
         serve_http2_unconditional(io, svc, listen_cancel_handle)
           .await
-          .map_err(|e| e.into())
+          .map_err(HttpNextError::Hyper)
       } else if Some(TLS_ALPN_HTTP_11) == handshake.as_deref() {
         serve_http11_unconditional(io, svc, listen_cancel_handle)
           .await
-          .map_err(|e| e.into())
+          .map_err(HttpNextError::Hyper)
       } else {
         serve_http2_autodetect(io, svc, listen_cancel_handle).await
       }
@@ -870,7 +895,7 @@ fn serve_http(
   request_info: HttpConnectionProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>> {
+) -> JoinHandle<Result<(), HttpNextError>> {
   let HttpLifetime {
     server_state,
     connection_cancel_handle,
@@ -891,7 +916,7 @@ fn serve_http_on<HTTP>(
   listen_properties: &HttpListenProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>>
+) -> JoinHandle<Result<(), HttpNextError>>
 where
   HTTP: HttpPropertyExtractor,
 {
@@ -922,7 +947,7 @@ struct HttpLifetime {
 }
 
 struct HttpJoinHandle {
-  join_handle: AsyncRefCell<Option<JoinHandle<Result<(), AnyError>>>>,
+  join_handle: AsyncRefCell<Option<JoinHandle<Result<(), HttpNextError>>>>,
   connection_cancel_handle: Rc<CancelHandle>,
   listen_cancel_handle: Rc<CancelHandle>,
   rx: AsyncRefCell<tokio::sync::mpsc::Receiver<Rc<HttpRecord>>>,
@@ -982,12 +1007,13 @@ impl Drop for HttpJoinHandle {
 pub fn op_http_serve<HTTP>(
   state: Rc<RefCell<OpState>>,
   #[smi] listener_rid: ResourceId,
-) -> Result<(ResourceId, &'static str, String), AnyError>
+) -> Result<(ResourceId, &'static str, String), HttpNextError>
 where
   HTTP: HttpPropertyExtractor,
 {
   let listener =
-    HTTP::get_listener_for_rid(&mut state.borrow_mut(), listener_rid)?;
+    HTTP::get_listener_for_rid(&mut state.borrow_mut(), listener_rid)
+      .map_err(HttpNextError::Resource)?;
 
   let listen_properties = HTTP::listen_properties_from_listener(&listener)?;
 
@@ -1002,7 +1028,8 @@ where
     loop {
       let conn = HTTP::accept_connection_from_listener(&listener)
         .try_or_cancel(listen_cancel_clone.clone())
-        .await?;
+        .await
+        .map_err(HttpNextError::HttpPropertyExtractor)?;
       serve_http_on::<HTTP>(
         conn,
         &listen_properties_clone,
@@ -1011,7 +1038,7 @@ where
       );
     }
     #[allow(unreachable_code)]
-    Ok::<_, AnyError>(())
+    Ok::<_, HttpNextError>(())
   });
 
   // Set the handle after we start the future
@@ -1031,25 +1058,25 @@ where
 pub fn op_http_serve_on<HTTP>(
   state: Rc<RefCell<OpState>>,
   #[smi] connection_rid: ResourceId,
-) -> Result<(ResourceId, &'static str, String), AnyError>
+) -> Result<(ResourceId, &'static str, String), HttpNextError>
 where
   HTTP: HttpPropertyExtractor,
 {
   let connection =
-    HTTP::get_connection_for_rid(&mut state.borrow_mut(), connection_rid)?;
+    HTTP::get_connection_for_rid(&mut state.borrow_mut(), connection_rid)
+      .map_err(HttpNextError::Resource)?;
 
   let listen_properties = HTTP::listen_properties_from_connection(&connection)?;
 
   let (tx, rx) = tokio::sync::mpsc::channel(10);
   let resource: Rc<HttpJoinHandle> = Rc::new(HttpJoinHandle::new(rx));
 
-  let handle: JoinHandle<Result<(), deno_core::anyhow::Error>> =
-    serve_http_on::<HTTP>(
-      connection,
-      &listen_properties,
-      resource.lifetime(),
-      tx,
-    );
+  let handle = serve_http_on::<HTTP>(
+    connection,
+    &listen_properties,
+    resource.lifetime(),
+    tx,
+  );
 
   // Set the handle after we start the future
   *RcRef::map(&resource, |this| &this.join_handle)
@@ -1095,12 +1122,13 @@ pub fn op_http_try_wait(
 pub async fn op_http_wait(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<*const c_void, AnyError> {
+) -> Result<*const c_void, HttpNextError> {
   // We will get the join handle initially, as we might be consuming requests still
   let join_handle = state
     .borrow_mut()
     .resource_table
-    .get::<HttpJoinHandle>(rid)?;
+    .get::<HttpJoinHandle>(rid)
+    .map_err(HttpNextError::Resource)?;
 
   let cancel = join_handle.listen_cancel_handle();
   let next = async {
@@ -1127,13 +1155,12 @@ pub async fn op_http_wait(
 
   // Filter out shutdown (ENOTCONN) errors
   if let Err(err) = res {
-    if let Some(err) = err.source() {
-      if let Some(err) = err.downcast_ref::<io::Error>() {
-        if err.kind() == io::ErrorKind::NotConnected {
-          return Ok(null());
-        }
+    if let HttpNextError::Io(err) = &err {
+      if err.kind() == io::ErrorKind::NotConnected {
+        return Ok(null());
       }
     }
+
     return Err(err);
   }
 
@@ -1146,7 +1173,7 @@ pub fn op_http_cancel(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   graceful: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let join_handle = state.resource_table.get::<HttpJoinHandle>(rid)?;
 
   if graceful {
@@ -1166,11 +1193,12 @@ pub async fn op_http_close(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   graceful: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpNextError> {
   let join_handle = state
     .borrow_mut()
     .resource_table
-    .take::<HttpJoinHandle>(rid)?;
+    .take::<HttpJoinHandle>(rid)
+    .map_err(HttpNextError::Resource)?;
 
   if graceful {
     http_general_trace!("graceful shutdown");
@@ -1216,23 +1244,26 @@ impl UpgradeStream {
     }
   }
 
-  async fn read(self: Rc<Self>, buf: &mut [u8]) -> Result<usize, AnyError> {
+  async fn read(
+    self: Rc<Self>,
+    buf: &mut [u8],
+  ) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let read = RcRef::map(self, |this| &this.read);
       let mut read = read.borrow_mut().await;
-      Ok(Pin::new(&mut *read).read(buf).await?)
+      Pin::new(&mut *read).read(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
   }
 
-  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, AnyError> {
+  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let write = RcRef::map(self, |this| &this.write);
       let mut write = write.borrow_mut().await;
-      Ok(Pin::new(&mut *write).write(buf).await?)
+      Pin::new(&mut *write).write(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
@@ -1242,7 +1273,7 @@ impl UpgradeStream {
     self: Rc<Self>,
     buf1: &[u8],
     buf2: &[u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.write).borrow_mut().await;
 
     let total = buf1.len() + buf2.len();
@@ -1295,9 +1326,12 @@ pub async fn op_raw_write_vectored(
   #[smi] rid: ResourceId,
   #[buffer] buf1: JsBuffer,
   #[buffer] buf2: JsBuffer,
-) -> Result<usize, AnyError> {
-  let resource: Rc<UpgradeStream> =
-    state.borrow().resource_table.get::<UpgradeStream>(rid)?;
+) -> Result<usize, HttpNextError> {
+  let resource: Rc<UpgradeStream> = state
+    .borrow()
+    .resource_table
+    .get::<UpgradeStream>(rid)
+    .map_err(HttpNextError::Resource)?;
   let nwritten = resource.write_vectored(&buf1, &buf2).await?;
   Ok(nwritten)
 }
diff --git a/ext/http/lib.rs b/ext/http/lib.rs
index 5461713aa..6243804a1 100644
--- a/ext/http/lib.rs
+++ b/ext/http/lib.rs
@@ -6,8 +6,6 @@ use async_compression::Level;
 use base64::prelude::BASE64_STANDARD;
 use base64::Engine;
 use cache_control::CacheControl;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::futures::channel::mpsc;
 use deno_core::futures::channel::oneshot;
 use deno_core::futures::future::pending;
@@ -89,11 +87,14 @@ mod service;
 mod websocket_upgrade;
 
 use fly_accept_encoding::Encoding;
+pub use http_next::HttpNextError;
 pub use request_properties::DefaultHttpPropertyExtractor;
 pub use request_properties::HttpConnectionProperties;
 pub use request_properties::HttpListenProperties;
 pub use request_properties::HttpPropertyExtractor;
 pub use request_properties::HttpRequestProperties;
+pub use service::UpgradeUnavailableError;
+pub use websocket_upgrade::WebSocketUpgradeError;
 
 deno_core::extension!(
   deno_http,
@@ -134,6 +135,38 @@ deno_core::extension!(
   esm = ["00_serve.ts", "01_http.js", "02_websocket.ts"],
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("{0}")]
+  HyperV014(#[source] Arc<hyper_v014::Error>),
+  #[error("{0}")]
+  InvalidHeaderName(#[from] hyper_v014::header::InvalidHeaderName),
+  #[error("{0}")]
+  InvalidHeaderValue(#[from] hyper_v014::header::InvalidHeaderValue),
+  #[error("{0}")]
+  Http(#[from] hyper_v014::http::Error),
+  #[error("response headers already sent")]
+  ResponseHeadersAlreadySent,
+  #[error("connection closed while sending response")]
+  ConnectionClosedWhileSendingResponse,
+  #[error("already in use")]
+  AlreadyInUse,
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error("no response headers")]
+  NoResponseHeaders,
+  #[error("response already completed")]
+  ResponseAlreadyCompleted,
+  #[error("cannot upgrade because request body was used")]
+  UpgradeBodyUsed,
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 pub enum HttpSocketAddr {
   IpSocket(std::net::SocketAddr),
   #[cfg(unix)]
@@ -216,7 +249,7 @@ impl HttpConnResource {
       String,
       String,
     )>,
-    AnyError,
+    HttpError,
   > {
     let fut = async {
       let (request_tx, request_rx) = oneshot::channel();
@@ -259,8 +292,8 @@ impl HttpConnResource {
   }
 
   /// A future that completes when this HTTP connection is closed or errors.
-  async fn closed(&self) -> Result<(), AnyError> {
-    self.closed_fut.clone().map_err(AnyError::from).await
+  async fn closed(&self) -> Result<(), HttpError> {
+    self.closed_fut.clone().map_err(HttpError::HyperV014).await
   }
 }
 
@@ -280,14 +313,13 @@ pub fn http_create_conn_resource<S, A>(
   io: S,
   addr: A,
   scheme: &'static str,
-) -> Result<ResourceId, AnyError>
+) -> ResourceId
 where
   S: AsyncRead + AsyncWrite + Unpin + Send + 'static,
   A: Into<HttpSocketAddr>,
 {
   let conn = HttpConnResource::new(io, scheme, addr.into());
-  let rid = state.resource_table.add(conn);
-  Ok(rid)
+  state.resource_table.add(conn)
 }
 
 /// An object that implements the `hyper::Service` trait, through which Hyper
@@ -423,7 +455,9 @@ impl Resource for HttpStreamReadResource {
             // safely call `await` on it without creating a race condition.
             Some(_) => match body.as_mut().next().await.unwrap() {
               Ok(chunk) => assert!(chunk.is_empty()),
-              Err(err) => break Err(AnyError::from(err)),
+              Err(err) => {
+                break Err(HttpError::HyperV014(Arc::new(err)).into())
+              }
             },
             None => break Ok(BufView::empty()),
           }
@@ -545,8 +579,12 @@ struct NextRequestResponse(
 async fn op_http_accept(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<NextRequestResponse>, AnyError> {
-  let conn = state.borrow().resource_table.get::<HttpConnResource>(rid)?;
+) -> Result<Option<NextRequestResponse>, HttpError> {
+  let conn = state
+    .borrow()
+    .resource_table
+    .get::<HttpConnResource>(rid)
+    .map_err(HttpError::Resource)?;
 
   match conn.accept().await {
     Ok(Some((read_stream, write_stream, method, url))) => {
@@ -657,11 +695,12 @@ async fn op_http_write_headers(
   #[smi] status: u16,
   #[serde] headers: Vec<(ByteString, ByteString)>,
   #[serde] data: Option<StringOrBuffer>,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow_mut()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
 
   // Track supported encoding
   let encoding = stream.accept_encoding;
@@ -708,14 +747,14 @@ async fn op_http_write_headers(
   let mut old_wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
   let response_tx = match replace(&mut *old_wr, new_wr) {
     HttpResponseWriter::Headers(response_tx) => response_tx,
-    _ => return Err(http_error("response headers already sent")),
+    _ => return Err(HttpError::ResponseHeadersAlreadySent),
   };
 
   match response_tx.send(body) {
     Ok(_) => Ok(()),
     Err(_) => {
       stream.conn.closed().await?;
-      Err(http_error("connection closed while sending response"))
+      Err(HttpError::ConnectionClosedWhileSendingResponse)
     }
   }
 }
@@ -725,11 +764,14 @@ async fn op_http_write_headers(
 fn op_http_headers(
   state: &mut OpState,
   #[smi] rid: u32,
-) -> Result<Vec<(ByteString, ByteString)>, AnyError> {
-  let stream = state.resource_table.get::<HttpStreamReadResource>(rid)?;
+) -> Result<Vec<(ByteString, ByteString)>, HttpError> {
+  let stream = state
+    .resource_table
+    .get::<HttpStreamReadResource>(rid)
+    .map_err(HttpError::Resource)?;
   let rd = RcRef::map(&stream, |r| &r.rd)
     .try_borrow()
-    .ok_or_else(|| http_error("already in use"))?;
+    .ok_or(HttpError::AlreadyInUse)?;
   match &*rd {
     HttpRequestReader::Headers(request) => Ok(req_headers(request.headers())),
     HttpRequestReader::Body(headers, _) => Ok(req_headers(headers)),
@@ -741,7 +783,7 @@ fn http_response(
   data: Option<StringOrBuffer>,
   compressing: bool,
   encoding: Encoding,
-) -> Result<(HttpResponseWriter, hyper_v014::Body), AnyError> {
+) -> Result<(HttpResponseWriter, hyper_v014::Body), HttpError> {
   // Gzip, after level 1, doesn't produce significant size difference.
   // This default matches nginx default gzip compression level (1):
   // https://nginx.org/en/docs/http/ngx_http_gzip_module.html#gzip_comp_level
@@ -878,25 +920,34 @@ async fn op_http_write_resource(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[smi] stream: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let http_stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&http_stream, |r| &r.wr).borrow_mut().await;
-  let resource = state.borrow().resource_table.get_any(stream)?;
+  let resource = state
+    .borrow()
+    .resource_table
+    .get_any(stream)
+    .map_err(HttpError::Resource)?;
   loop {
     match *wr {
       HttpResponseWriter::Headers(_) => {
-        return Err(http_error("no response headers"))
+        return Err(HttpError::NoResponseHeaders)
       }
       HttpResponseWriter::Closed => {
-        return Err(http_error("response already completed"))
+        return Err(HttpError::ResponseAlreadyCompleted)
       }
       _ => {}
     };
 
-    let view = resource.clone().read(64 * 1024).await?; // 64KB
+    let view = resource
+      .clone()
+      .read(64 * 1024)
+      .await
+      .map_err(HttpError::Other)?; // 64KB
     if view.is_empty() {
       break;
     }
@@ -937,16 +988,17 @@ async fn op_http_write(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] buf: JsBuffer,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
 
   match &mut *wr {
-    HttpResponseWriter::Headers(_) => Err(http_error("no response headers")),
-    HttpResponseWriter::Closed => Err(http_error("response already completed")),
+    HttpResponseWriter::Headers(_) => Err(HttpError::NoResponseHeaders),
+    HttpResponseWriter::Closed => Err(HttpError::ResponseAlreadyCompleted),
     HttpResponseWriter::Body { writer, .. } => {
       let mut result = writer.write_all(&buf).await;
       if result.is_ok() {
@@ -961,7 +1013,7 @@ async fn op_http_write(
           stream.conn.closed().await?;
           // If there was no connection error, drop body_tx.
           *wr = HttpResponseWriter::Closed;
-          Err(http_error("response already completed"))
+          Err(HttpError::ResponseAlreadyCompleted)
         }
       }
     }
@@ -975,7 +1027,7 @@ async fn op_http_write(
           stream.conn.closed().await?;
           // If there was no connection error, drop body_tx.
           *wr = HttpResponseWriter::Closed;
-          Err(http_error("response already completed"))
+          Err(HttpError::ResponseAlreadyCompleted)
         }
       }
     }
@@ -989,11 +1041,12 @@ async fn op_http_write(
 async fn op_http_shutdown(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
   let wr = take(&mut *wr);
   match wr {
@@ -1022,14 +1075,12 @@ async fn op_http_shutdown(
 
 #[op2]
 #[string]
-fn op_http_websocket_accept_header(
-  #[string] key: String,
-) -> Result<String, AnyError> {
+fn op_http_websocket_accept_header(#[string] key: String) -> String {
   let digest = ring::digest::digest(
     &ring::digest::SHA1_FOR_LEGACY_USE_ONLY,
     format!("{key}258EAFA5-E914-47DA-95CA-C5AB0DC85B11").as_bytes(),
   );
-  Ok(BASE64_STANDARD.encode(digest))
+  BASE64_STANDARD.encode(digest)
 }
 
 #[op2(async)]
@@ -1037,22 +1088,24 @@ fn op_http_websocket_accept_header(
 async fn op_http_upgrade_websocket(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpError> {
   let stream = state
     .borrow_mut()
     .resource_table
-    .get::<HttpStreamReadResource>(rid)?;
+    .get::<HttpStreamReadResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut rd = RcRef::map(&stream, |r| &r.rd).borrow_mut().await;
 
   let request = match &mut *rd {
     HttpRequestReader::Headers(request) => request,
-    _ => {
-      return Err(http_error("cannot upgrade because request body was used"))
-    }
+    _ => return Err(HttpError::UpgradeBodyUsed),
   };
 
-  let (transport, bytes) =
-    extract_network_stream(hyper_v014::upgrade::on(request).await?);
+  let (transport, bytes) = extract_network_stream(
+    hyper_v014::upgrade::on(request)
+      .await
+      .map_err(|err| HttpError::HyperV014(Arc::new(err)))?,
+  );
   Ok(ws_create_server_stream(
     &mut state.borrow_mut(),
     transport,
@@ -1084,10 +1137,6 @@ where
   }
 }
 
-fn http_error(message: &'static str) -> AnyError {
-  custom_error("Http", message)
-}
-
 /// Filters out the ever-surprising 'shutdown ENOTCONN' errors.
 fn filter_enotconn(
   result: Result<(), hyper_v014::Error>,
diff --git a/ext/http/request_body.rs b/ext/http/request_body.rs
index 45df12457..f1c3f358e 100644
--- a/ext/http/request_body.rs
+++ b/ext/http/request_body.rs
@@ -1,9 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 use bytes::Bytes;
-use deno_core::error::AnyError;
 use deno_core::futures::stream::Peekable;
 use deno_core::futures::Stream;
 use deno_core::futures::StreamExt;
+use deno_core::futures::TryFutureExt;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
 use deno_core::BufView;
@@ -22,7 +22,7 @@ use std::task::Poll;
 struct ReadFuture(Incoming);
 
 impl Stream for ReadFuture {
-  type Item = Result<Bytes, AnyError>;
+  type Item = Result<Bytes, hyper::Error>;
 
   fn poll_next(
     self: Pin<&mut Self>,
@@ -37,13 +37,13 @@ impl Stream for ReadFuture {
           if let Ok(data) = frame.into_data() {
             // Ensure that we never yield an empty frame
             if !data.is_empty() {
-              break Poll::Ready(Some(Ok::<_, AnyError>(data)));
+              break Poll::Ready(Some(Ok(data)));
             }
           }
           // Loop again so we don't lose the waker
           continue;
         }
-        Some(Err(e)) => Poll::Ready(Some(Err(e.into()))),
+        Some(Err(e)) => Poll::Ready(Some(Err(e))),
         None => Poll::Ready(None),
       };
     }
@@ -58,7 +58,7 @@ impl HttpRequestBody {
     Self(AsyncRefCell::new(ReadFuture(body).peekable()), size_hint)
   }
 
-  async fn read(self: Rc<Self>, limit: usize) -> Result<BufView, AnyError> {
+  async fn read(self: Rc<Self>, limit: usize) -> Result<BufView, hyper::Error> {
     let peekable = RcRef::map(self, |this| &this.0);
     let mut peekable = peekable.borrow_mut().await;
     match Pin::new(&mut *peekable).peek_mut().await {
@@ -82,7 +82,7 @@ impl Resource for HttpRequestBody {
   }
 
   fn read(self: Rc<Self>, limit: usize) -> AsyncResult<BufView> {
-    Box::pin(HttpRequestBody::read(self, limit))
+    Box::pin(HttpRequestBody::read(self, limit).map_err(Into::into))
   }
 
   fn size_hint(&self) -> (u64, Option<u64>) {
diff --git a/ext/http/service.rs b/ext/http/service.rs
index 787e9babf..75f93d77c 100644
--- a/ext/http/service.rs
+++ b/ext/http/service.rs
@@ -2,7 +2,6 @@
 use crate::request_properties::HttpConnectionProperties;
 use crate::response_body::ResponseBytesInner;
 use crate::response_body::ResponseStreamResult;
-use deno_core::error::AnyError;
 use deno_core::futures::ready;
 use deno_core::BufView;
 use deno_core::OpState;
@@ -206,6 +205,10 @@ pub(crate) async fn handle_request(
   Ok(response)
 }
 
+#[derive(Debug, thiserror::Error)]
+#[error("upgrade unavailable")]
+pub struct UpgradeUnavailableError;
+
 struct HttpRecordInner {
   server_state: SignallingRc<HttpServerState>,
   request_info: HttpConnectionProperties,
@@ -344,14 +347,14 @@ impl HttpRecord {
   }
 
   /// Perform the Hyper upgrade on this record.
-  pub fn upgrade(&self) -> Result<OnUpgrade, AnyError> {
+  pub fn upgrade(&self) -> Result<OnUpgrade, UpgradeUnavailableError> {
     // Manually perform the upgrade. We're peeking into hyper's underlying machinery here a bit
     self
       .self_mut()
       .request_parts
       .extensions
       .remove::<OnUpgrade>()
-      .ok_or_else(|| AnyError::msg("upgrade unavailable"))
+      .ok_or(UpgradeUnavailableError)
   }
 
   /// Take the Hyper body from this record.
@@ -515,7 +518,7 @@ pub struct HttpRecordResponse(ManuallyDrop<Rc<HttpRecord>>);
 
 impl Body for HttpRecordResponse {
   type Data = BufView;
-  type Error = AnyError;
+  type Error = deno_core::error::AnyError;
 
   fn poll_frame(
     self: Pin<&mut Self>,
@@ -640,7 +643,7 @@ mod tests {
   }
 
   #[tokio::test]
-  async fn test_handle_request() -> Result<(), AnyError> {
+  async fn test_handle_request() -> Result<(), deno_core::error::AnyError> {
     let (tx, mut rx) = tokio::sync::mpsc::channel(10);
     let server_state = HttpServerState::new();
     let server_state_check = server_state.clone();
diff --git a/ext/http/websocket_upgrade.rs b/ext/http/websocket_upgrade.rs
index 4dead767a..af9504717 100644
--- a/ext/http/websocket_upgrade.rs
+++ b/ext/http/websocket_upgrade.rs
@@ -4,7 +4,6 @@ use std::marker::PhantomData;
 
 use bytes::Bytes;
 use bytes::BytesMut;
-use deno_core::error::AnyError;
 use httparse::Status;
 use hyper::header::HeaderName;
 use hyper::header::HeaderValue;
@@ -13,12 +12,30 @@ use memmem::Searcher;
 use memmem::TwoWaySearcher;
 use once_cell::sync::OnceCell;
 
-use crate::http_error;
+#[derive(Debug, thiserror::Error)]
+pub enum WebSocketUpgradeError {
+  #[error("invalid headers")]
+  InvalidHeaders,
+  #[error("{0}")]
+  HttpParse(#[from] httparse::Error),
+  #[error("{0}")]
+  Http(#[from] http::Error),
+  #[error("{0}")]
+  Utf8(#[from] std::str::Utf8Error),
+  #[error("{0}")]
+  InvalidHeaderName(#[from] http::header::InvalidHeaderName),
+  #[error("{0}")]
+  InvalidHeaderValue(#[from] http::header::InvalidHeaderValue),
+  #[error("invalid HTTP status line")]
+  InvalidHttpStatusLine,
+  #[error("attempted to write to completed upgrade buffer")]
+  UpgradeBufferAlreadyCompleted,
+}
 
 /// Given a buffer that ends in `\n\n` or `\r\n\r\n`, returns a parsed [`Request<Body>`].
 fn parse_response<T: Default>(
   header_bytes: &[u8],
-) -> Result<(usize, Response<T>), AnyError> {
+) -> Result<(usize, Response<T>), WebSocketUpgradeError> {
   let mut headers = [httparse::EMPTY_HEADER; 16];
   let status = httparse::parse_headers(header_bytes, &mut headers)?;
   match status {
@@ -32,7 +49,7 @@ fn parse_response<T: Default>(
       }
       Ok((index, resp))
     }
-    _ => Err(http_error("invalid headers")),
+    _ => Err(WebSocketUpgradeError::InvalidHeaders),
   }
 }
 
@@ -69,11 +86,14 @@ pub struct WebSocketUpgrade<T: Default> {
 impl<T: Default> WebSocketUpgrade<T> {
   /// Ensures that the status line starts with "HTTP/1.1 101 " which matches all of the node.js
   /// WebSocket libraries that are known. We don't care about the trailing status text.
-  fn validate_status(&self, status: &[u8]) -> Result<(), AnyError> {
+  fn validate_status(
+    &self,
+    status: &[u8],
+  ) -> Result<(), WebSocketUpgradeError> {
     if status.starts_with(b"HTTP/1.1 101 ") {
       Ok(())
     } else {
-      Err(http_error("invalid HTTP status line"))
+      Err(WebSocketUpgradeError::InvalidHttpStatusLine)
     }
   }
 
@@ -82,7 +102,7 @@ impl<T: Default> WebSocketUpgrade<T> {
   pub fn write(
     &mut self,
     bytes: &[u8],
-  ) -> Result<Option<(Response<T>, Bytes)>, AnyError> {
+  ) -> Result<Option<(Response<T>, Bytes)>, WebSocketUpgradeError> {
     use WebSocketUpgradeState::*;
 
     match self.state {
@@ -142,9 +162,7 @@ impl<T: Default> WebSocketUpgrade<T> {
           Ok(None)
         }
       }
-      Complete => {
-        Err(http_error("attempted to write to completed upgrade buffer"))
-      }
+      Complete => Err(WebSocketUpgradeError::UpgradeBufferAlreadyCompleted),
     }
   }
 }
@@ -157,8 +175,8 @@ mod tests {
   type ExpectedResponseAndHead = Option<(Response<Body>, &'static [u8])>;
 
   fn assert_response(
-    result: Result<Option<(Response<Body>, Bytes)>, AnyError>,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    result: Result<Option<(Response<Body>, Bytes)>, WebSocketUpgradeError>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
     chunk_info: Option<(usize, usize)>,
   ) {
     let formatted = format!("{result:?}");
@@ -189,8 +207,8 @@ mod tests {
         "Expected Ok(None), was {formatted}",
       ),
       Err(e) => assert_eq!(
-        e,
-        result.err().map(|e| format!("{e:?}")).unwrap_or_default(),
+        format!("{e:?}"),
+        format!("{:?}", result.unwrap_err()),
         "Expected error, was {formatted}",
       ),
     }
@@ -198,7 +216,7 @@ mod tests {
 
   fn validate_upgrade_all_at_once(
     s: &str,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     let mut upgrade = WebSocketUpgrade::default();
     let res = upgrade.write(s.as_bytes());
@@ -209,7 +227,7 @@ mod tests {
   fn validate_upgrade_chunks(
     s: &str,
     size: usize,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     let chunk_info = Some((s.as_bytes().len(), size));
     let mut upgrade = WebSocketUpgrade::default();
@@ -226,7 +244,7 @@ mod tests {
 
   fn validate_upgrade(
     s: &str,
-    expected: fn() -> Result<ExpectedResponseAndHead, &'static str>,
+    expected: fn() -> Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     validate_upgrade_all_at_once(s, expected());
     validate_upgrade_chunks(s, 1, expected());
@@ -315,7 +333,7 @@ mod tests {
   #[test]
   fn upgrade_invalid_status() {
     validate_upgrade("HTTP/1.1 200 OK\nConnection: Upgrade\n\n", || {
-      Err("invalid HTTP status line")
+      Err(WebSocketUpgradeError::InvalidHttpStatusLine)
     });
   }
 
@@ -327,7 +345,11 @@ mod tests {
       .join("\n");
     validate_upgrade(
       &format!("HTTP/1.1 101 Switching Protocols\n{headers}\n\n"),
-      || Err("too many headers"),
+      || {
+        Err(WebSocketUpgradeError::HttpParse(
+          httparse::Error::TooManyHeaders,
+        ))
+      },
     );
   }
 }
diff --git a/runtime/errors.rs b/runtime/errors.rs
index 45442a11c..dcd626dc6 100644
--- a/runtime/errors.rs
+++ b/runtime/errors.rs
@@ -29,6 +29,9 @@ use deno_ffi::IRError;
 use deno_ffi::ReprError;
 use deno_ffi::StaticError;
 use deno_fs::FsOpsError;
+use deno_http::HttpError;
+use deno_http::HttpNextError;
+use deno_http::WebSocketUpgradeError;
 use deno_io::fs::FsError;
 use deno_kv::KvCheckError;
 use deno_kv::KvError;
@@ -682,6 +685,59 @@ fn get_net_map_error(error: &deno_net::io::MapError) -> &'static str {
   }
 }
 
+fn get_http_error(error: &HttpError) -> &'static str {
+  match error {
+    HttpError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    HttpError::HyperV014(e) => get_hyper_v014_error_class(e),
+    HttpError::InvalidHeaderName(_) => "Error",
+    HttpError::InvalidHeaderValue(_) => "Error",
+    HttpError::Http(_) => "Error",
+    HttpError::ResponseHeadersAlreadySent => "Http",
+    HttpError::ConnectionClosedWhileSendingResponse => "Http",
+    HttpError::AlreadyInUse => "Http",
+    HttpError::Io(e) => get_io_error_class(e),
+    HttpError::NoResponseHeaders => "Http",
+    HttpError::ResponseAlreadyCompleted => "Http",
+    HttpError::UpgradeBodyUsed => "Http",
+    HttpError::Resource(e) | HttpError::Other(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+  }
+}
+
+fn get_http_next_error(error: &HttpNextError) -> &'static str {
+  match error {
+    HttpNextError::Io(e) => get_io_error_class(e),
+    HttpNextError::WebSocketUpgrade(e) => get_websocket_upgrade_error(e),
+    HttpNextError::Hyper(e) => get_hyper_error_class(e),
+    HttpNextError::JoinError(_) => "Error",
+    HttpNextError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    HttpNextError::UpgradeUnavailable(_) => "Error",
+    HttpNextError::HttpPropertyExtractor(e) | HttpNextError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+  }
+}
+
+fn get_websocket_upgrade_error(error: &WebSocketUpgradeError) -> &'static str {
+  match error {
+    WebSocketUpgradeError::InvalidHeaders => "Http",
+    WebSocketUpgradeError::HttpParse(_) => "Error",
+    WebSocketUpgradeError::Http(_) => "Error",
+    WebSocketUpgradeError::Utf8(_) => "Error",
+    WebSocketUpgradeError::InvalidHeaderName(_) => "Error",
+    WebSocketUpgradeError::InvalidHeaderValue(_) => "Error",
+    WebSocketUpgradeError::InvalidHttpStatusLine => "Http",
+    WebSocketUpgradeError::UpgradeBufferAlreadyCompleted => "Http",
+  }
+}
+
 pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
   deno_core::error::get_custom_error_class(e)
     .or_else(|| deno_webgpu::error::get_error_class_name(e))
@@ -702,6 +758,12 @@ pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
     .or_else(|| e.downcast_ref::<BlobError>().map(get_web_blob_error_class))
     .or_else(|| e.downcast_ref::<IRError>().map(|_| "TypeError"))
     .or_else(|| e.downcast_ref::<ReprError>().map(get_ffi_repr_error_class))
+    .or_else(|| e.downcast_ref::<HttpError>().map(get_http_error))
+    .or_else(|| e.downcast_ref::<HttpNextError>().map(get_http_next_error))
+    .or_else(|| {
+      e.downcast_ref::<WebSocketUpgradeError>()
+        .map(get_websocket_upgrade_error)
+    })
     .or_else(|| e.downcast_ref::<FsOpsError>().map(get_fs_error))
     .or_else(|| {
       e.downcast_ref::<DlfcnError>()
diff --git a/runtime/ops/http.rs b/runtime/ops/http.rs
index cec8b0ef8..cbabbe22c 100644
--- a/runtime/ops/http.rs
+++ b/runtime/ops/http.rs
@@ -34,7 +34,7 @@ fn op_http_start(
     let (read_half, write_half) = resource.into_inner();
     let tcp_stream = read_half.reunite(write_half)?;
     let addr = tcp_stream.local_addr()?;
-    return http_create_conn_resource(state, tcp_stream, addr, "http");
+    return Ok(http_create_conn_resource(state, tcp_stream, addr, "http"));
   }
 
   if let Ok(resource_rc) = state
@@ -49,7 +49,7 @@ fn op_http_start(
     let (read_half, write_half) = resource.into_inner();
     let tls_stream = read_half.unsplit(write_half);
     let addr = tls_stream.local_addr()?;
-    return http_create_conn_resource(state, tls_stream, addr, "https");
+    return Ok(http_create_conn_resource(state, tls_stream, addr, "https"));
   }
 
   #[cfg(unix)]
@@ -65,7 +65,12 @@ fn op_http_start(
     let (read_half, write_half) = resource.into_inner();
     let unix_stream = read_half.reunite(write_half)?;
     let addr = unix_stream.local_addr()?;
-    return http_create_conn_resource(state, unix_stream, addr, "http+unix");
+    return Ok(http_create_conn_resource(
+      state,
+      unix_stream,
+      addr,
+      "http+unix",
+    ));
   }
 
   Err(bad_resource_id())