diff --git a/lib/body.ml b/lib/body.ml
index c6f2bab..de74ea2 100644
--- a/lib/body.ml
+++ b/lib/body.ml
@@ -151,27 +151,41 @@ module Writer = struct
     t
 
   let write_char t c =
-    Faraday.write_char t.faraday c
+    if not (Faraday.is_closed t.faraday) then
+      Faraday.write_char t.faraday c
 
   let write_string t ?off ?len s =
-    Faraday.write_string ?off ?len t.faraday s
+    if not (Faraday.is_closed t.faraday) then
+      Faraday.write_string ?off ?len t.faraday s
 
   let write_bigstring t ?off ?len b =
-    Faraday.write_bigstring ?off ?len t.faraday b
+    if not (Faraday.is_closed t.faraday) then
+      Faraday.write_bigstring ?off ?len t.faraday b
 
   let schedule_bigstring t ?off ?len (b:Bigstringaf.t) =
-    Faraday.schedule_bigstring ?off ?len t.faraday b
+    if not (Faraday.is_closed t.faraday) then
+      Faraday.schedule_bigstring ?off ?len t.faraday b
 
   let ready_to_write t = Serialize.Writer.wakeup t.writer
 
   let flush t kontinue =
-    Faraday.flush t.faraday (fun () ->
-      Serialize.Writer.flush t.writer kontinue);
-    ready_to_write t
+    if Serialize.Writer.is_closed t.writer then
+      kontinue `Closed
+    else begin
+      Faraday.flush_with_reason t.faraday (function
+        | Drain -> kontinue `Closed
+        | Nothing_pending | Shift -> Serialize.Writer.flush t.writer kontinue);
+      ready_to_write t
+    end
 
   let is_closed t =
     Faraday.is_closed t.faraday
 
+  let close_and_drain t =
+    Faraday.close t.faraday;
+    (* Resolve all pending flushes *)
+    ignore (Faraday.drain t.faraday : int)
+
   let close t =
     Serialize.Writer.unyield t.writer;
     Faraday.close t.faraday;
@@ -202,6 +216,9 @@ module Writer = struct
 
   let transfer_to_writer t =
     let faraday = t.faraday in
+    if Serialize.Writer.is_closed t.writer then
+      close_and_drain t
+    else
     begin match Faraday.operation faraday with
     | `Yield -> ()
     | `Close ->
@@ -222,9 +239,11 @@ module Writer = struct
         | Identity  -> Serialize.Writer.schedule_fixed t.writer iovecs
         | Chunked _ -> Serialize.Writer.schedule_chunk t.writer iovecs
         end;
-        Serialize.Writer.flush t.writer (fun () ->
-          Faraday.shift faraday lengthv;
-          t.buffered_bytes <- t.buffered_bytes - lengthv)
+        Serialize.Writer.flush t.writer (function
+          | `Closed -> close_and_drain t
+          | `Written ->
+            Faraday.shift faraday lengthv;
+            t.buffered_bytes <- t.buffered_bytes - lengthv)
       end
     end
 end
diff --git a/lib/httpun.mli b/lib/httpun.mli
index 4ed24df..628c8cf 100644
--- a/lib/httpun.mli
+++ b/lib/httpun.mli
@@ -97,9 +97,11 @@ module Body : sig
         modified until a subsequent call to {!flush} has successfully
         completed. *)
 
-    val flush : t -> (unit -> unit) -> unit
-    (** [flush t f] makes all bytes in [t] available for writing to the awaiting
-        output channel. Once those bytes have reached that output channel, [f]
+    val flush : t -> ([ `Written | `Closed ] -> unit) -> unit
+    (** [flush t f] makes all bytes in [t] available for writing to the
+        awaiting output channel. Once those bytes have reached that output
+        channel, [f `Written] will be called. If instead, the output channel is
+        closed before all of those bytes are successfully written, [f `Closed]
         will be called.
 
         The type of the output channel is runtime-dependent, as are guarantees
@@ -112,8 +114,9 @@ module Body : sig
         to the output channel. *)
 
     val is_closed : t -> bool
-    (** [is_closed t] is [true] if {!close} has been called on [t] and [false]
-        otherwise. A closed [t] may still have pending output. *)
+    (** [is_closed t] is [true] if {!close} has been called on [t], or if the
+        attached output channel is closed (e.g. because [report_write_result
+        `Closed] has been called). A closed [t] may still have pending output. *)
   end
 
 end
diff --git a/lib/reqd.ml b/lib/reqd.ml
index 8ef0d86..4749269 100644
--- a/lib/reqd.ml
+++ b/lib/reqd.ml
@@ -178,7 +178,9 @@ let unsafe_respond_with_upgrade t headers upgrade_handler =
     if t.persistent then
       t.persistent <- Response.persistent_connection response;
     t.response_state <- Upgrade (response, upgrade_handler);
-    Writer.flush t.writer upgrade_handler;
+    Writer.flush t.writer (fun _reason ->
+      (* TODO(anmonteiro): probably need to check `Closed here? *)
+      upgrade_handler ());
     Body.Reader.close t.request_body;
     Writer.wakeup t.writer
   | Streaming _ | Upgrade _ ->
diff --git a/lib/serialize.ml b/lib/serialize.ml
index 116e7fa..ce220df 100644
--- a/lib/serialize.ml
+++ b/lib/serialize.ml
@@ -158,13 +158,19 @@ module Writer = struct
   ;;
 
   let flush t f =
-    flush t.encoder f
+    flush_with_reason t.encoder (fun reason ->
+      let result =
+        match reason with
+        | Nothing_pending | Shift -> `Written
+        | Drain -> `Closed
+      in
+      f result)
 
   let unyield t =
     (* This would be better implemented by a function that just takes the
        encoder out of a yielded state if it's in that state. Requires a change
        to the faraday library. *)
-    flush t (fun () -> ())
+    flush t (fun _reason -> ())
 
   let yield t =
     Faraday.yield t.encoder
diff --git a/lib_test/test_client_connection.ml b/lib_test/test_client_connection.ml
index e434dfd..85a6ead 100644
--- a/lib_test/test_client_connection.ml
+++ b/lib_test/test_client_connection.ml
@@ -1775,8 +1775,7 @@ let test_flush_response_before_shutdown () =
     true
     (Body.Writer.is_closed body);
 
-  raises_writer_closed (fun () ->
-    write_string t "b\r\nhello world\r\n");
+  writer_closed t;
   connection_is_shutdown t
 ;;
 
diff --git a/lib_test/test_server_connection.ml b/lib_test/test_server_connection.ml
index 2eb026d..b182788 100644
--- a/lib_test/test_server_connection.ml
+++ b/lib_test/test_server_connection.ml
@@ -326,8 +326,9 @@ let echo_handler response reqd =
   let response_body = Reqd.respond_with_streaming reqd response in
   let rec on_read buffer ~off ~len =
     Body.Writer.write_string response_body (Bigstringaf.substring ~off ~len buffer);
-    Body.Writer.flush response_body (fun () ->
-      Body.Reader.schedule_read request_body ~on_eof ~on_read)
+    Body.Writer.flush response_body (function
+      | `Closed -> assert false
+      | `Written -> Body.Reader.schedule_read request_body ~on_eof ~on_read)
   and on_eof () =
     print_endline "echo handler eof";
     Body.Writer.close response_body
@@ -340,17 +341,20 @@ let streaming_handler ?(flush=false) ?(error=false) response writes reqd =
   let request_body = Reqd.request_body reqd in
   Body.Reader.close request_body;
   let body = Reqd.respond_with_streaming ~flush_headers_immediately:flush reqd response in
-  let rec write () =
-    match !writes with
-    | [] -> (match error with
-      | false -> Body.Writer.close body
-      | true -> Reqd.report_exn reqd (Failure "exn"))
-    | w :: ws ->
-      Body.Writer.write_string body w;
-      writes := ws;
-      Body.Writer.flush body write
-  in
-  write ();
+  let rec write reason =
+    match reason with
+    | `Closed -> assert false
+    | `Written ->
+      match !writes with
+      | [] -> (match error with
+        | false -> Body.Writer.close body
+        | true -> Reqd.report_exn reqd (Failure "exn"))
+      | w :: ws ->
+        Body.Writer.write_string body w;
+        writes := ws;
+        Body.Writer.flush body write
+  in
+  write `Written;
 ;;
 
 let synchronous_raise reqd =
@@ -875,9 +879,11 @@ let test_chunked_encoding () =
     let response = Response.create `OK ~headers:Headers.encoding_chunked in
     let resp_body = Reqd.respond_with_streaming reqd response in
     Body.Writer.write_string resp_body "First chunk";
-    Body.Writer.flush resp_body (fun () ->
-      Body.Writer.write_string resp_body "Second chunk";
-      Body.Writer.close resp_body);
+    Body.Writer.flush resp_body (function
+      | `Closed -> assert false
+      | `Written ->
+        Body.Writer.write_string resp_body "Second chunk";
+        Body.Writer.close resp_body);
   in
   let t = create ~error_handler request_handler in
   writer_yielded t;
@@ -903,9 +909,11 @@ let test_chunked_encoding_for_error () =
       `Bad_request error;
     let body = start_response Headers.encoding_chunked in
     Body.Writer.write_string body "Bad";
-    Body.Writer.flush body (fun () ->
-      Body.Writer.write_string body " request";
-      Body.Writer.close body);
+    Body.Writer.flush body (function
+      | `Closed -> assert false
+      | `Written ->
+        Body.Writer.write_string body " request";
+        Body.Writer.close body);
   in
   let t = create ~error_handler (fun _ -> assert false) in
   let c = feed_string t "  X\r\n\r\n" in
@@ -1079,10 +1087,12 @@ let streaming_error_handler
   let resp_body = start_response headers in
   continue_error := (fun () ->
     Body.Writer.write_string resp_body "got an error\n";
-    Body.Writer.flush resp_body (fun () ->
-      continue_error := (fun () ->
-          Body.Writer.write_string resp_body "more output";
-          Body.Writer.close resp_body)))
+    Body.Writer.flush resp_body (function
+      | `Closed -> assert false
+      | `Written ->
+        continue_error := (fun () ->
+            Body.Writer.write_string resp_body "more output";
+            Body.Writer.close resp_body)))
 ;;
 
 let test_malformed_request_streaming_error_response () =
@@ -1119,13 +1129,17 @@ let chunked_error_handler continue_error ?request:_ _error start_response =
     start_response (Headers.of_list ["transfer-encoding", "chunked"])
   in
   Body.Writer.write_string resp_body "chunk 1\n";
-  Body.Writer.flush resp_body (fun () ->
-    continue_error := (fun () ->
-      Body.Writer.write_string resp_body "chunk 2\n";
-      Body.Writer.flush resp_body (fun () ->
-        continue_error := (fun () ->
-          Body.Writer.write_string resp_body "chunk 3\n";
-          Body.Writer.close resp_body))))
+  Body.Writer.flush resp_body (function
+    | `Closed -> assert false
+    | `Written ->
+      continue_error := (fun () ->
+        Body.Writer.write_string resp_body "chunk 2\n";
+        Body.Writer.flush resp_body (function
+          | `Closed -> assert false
+          | `Written ->
+            continue_error := (fun () ->
+              Body.Writer.write_string resp_body "chunk 3\n";
+              Body.Writer.close resp_body))))
 ;;
 
 let test_malformed_request_chunked_error_response () =
@@ -1475,9 +1489,11 @@ let test_streaming_response_before_reading_entire_body_no_error () =
       let resp_body = Reqd.respond_with_streaming reqd response in
       continue_response := (fun () ->
         Body.Writer.write_string resp_body "hello";
-        Body.Writer.flush resp_body (fun () ->
-          continue_response := (fun () ->
-            Body.Writer.close resp_body))))
+        Body.Writer.flush resp_body (function
+          | `Closed -> assert false
+          | `Written ->
+            continue_response := (fun () ->
+              Body.Writer.close resp_body))))
   in
   let error_handler ?request:_ _error _start_response = assert false in
   let t = create ~error_handler request_handler in
@@ -1748,9 +1764,11 @@ let test_race_condition_writer_issues_yield_after_reader_eof () =
          ~on_eof:(fun () ->
            let resp_body = Reqd.respond_with_streaming reqd response in
            Body.Writer.write_string resp_body (String.make 10 'a');
-           Body.Writer.flush resp_body (fun () ->
-             continue_response := (fun () ->
-                 Body.Writer.close resp_body))))
+           Body.Writer.flush resp_body (function
+             | `Closed -> assert false
+             | `Written ->
+               continue_response := (fun () ->
+                   Body.Writer.close resp_body))))
   in
   let t = create ~error_handler response_handler in
   let request =
@@ -1870,9 +1888,11 @@ let test_errored_chunked_streaming_response_async () =
     Body.Reader.close request_body;
     let body = Reqd.respond_with_streaming reqd response in
     Body.Writer.write_string body "hello";
-    Body.Writer.flush body (fun () ->
-    continue := (fun () ->
-      Reqd.report_exn reqd (Failure "heh")))
+    Body.Writer.flush body (function
+      | `Closed -> assert false
+      | `Written ->
+        continue := (fun () ->
+          Reqd.report_exn reqd (Failure "heh")))
   in
 
   let t = create request_handler in
@@ -2060,9 +2080,8 @@ let test_flush_response_before_shutdown () =
   write_response t response;
   !continue ();
   shutdown t;
-  raises_writer_closed (fun () ->
-    write_string t "b\r\nhello world\r\n";
-    connection_is_shutdown t);
+  write_string t "b\r\nhello world\r\n";
+  connection_is_shutdown t
 ;;
 
 let test_schedule_read_with_data_available () =
@@ -2286,7 +2305,10 @@ let test_body_flush_after_bytes_in_the_wire () =
     Response.create ~headers:(Headers.of_list ["content-length", "5"]) `OK
   in
   let callback_called = ref false in
-  let callback () = callback_called := true in
+  let callback = function
+    | `Closed -> assert false
+    | `Written -> callback_called := true
+  in
   let request_handler ~flush_headers_immediately reqd =
     let response_body =
       Reqd.respond_with_streaming