diff --git a/conn.go b/conn.go
index ef83a31..6201f90 100644
--- a/conn.go
+++ b/conn.go
@@ -333,7 +333,7 @@ func (c *Conn) send(_ context.Context, m *anyMessage, wait bool) (cc *call, err
 	// From here on, if we fail to send this, then we need to remove
 	// this from the pending map so we don't block on it or pile up
 	// pending entries for unsent messages.
-	defer func() {
+	defer func(cc *call) {
 		if err != nil {
 			if cc != nil {
 				c.mu.Lock()
@@ -341,7 +341,7 @@ func (c *Conn) send(_ context.Context, m *anyMessage, wait bool) (cc *call, err
 				c.mu.Unlock()
 			}
 		}
-	}()
+	}(cc)
 
 	if err := c.stream.WriteObject(m); err != nil {
 		return nil, err
diff --git a/conn_internal_test.go b/conn_internal_test.go
new file mode 100644
index 0000000..ad4f2db
--- /dev/null
+++ b/conn_internal_test.go
@@ -0,0 +1,111 @@
+package jsonrpc2
+
+import (
+	"context"
+	"errors"
+	"io"
+	"testing"
+)
+
+func TestConnFailedWriteCleanup(t *testing.T) {
+	tests := []struct {
+		name string
+		send func(*testing.T, *Conn) error
+	}{
+		{name: "dispatch", send: func(t *testing.T, c *Conn) error {
+			w, err := c.DispatchCall(context.Background(), "failed", nil)
+			if w.call != nil {
+				t.Error("failed dispatch returned a waiter")
+			}
+			return err
+		}},
+		{name: "string ID", send: func(t *testing.T, c *Conn) error {
+			_, err := c.DispatchCall(context.Background(), "failed", nil, StringID())
+			return err
+		}},
+		{name: "custom ID", send: func(t *testing.T, c *Conn) error {
+			_, err := c.DispatchCall(context.Background(), "failed", nil, PickID(ID{Num: 42}))
+			return err
+		}},
+		{name: "custom string ID", send: func(t *testing.T, c *Conn) error {
+			_, err := c.DispatchCall(context.Background(), "failed", nil, PickID(ID{Str: "failed", IsString: true}))
+			return err
+		}},
+		{name: "call", send: func(t *testing.T, c *Conn) error {
+			return c.Call(context.Background(), "failed", nil, nil)
+		}},
+		{name: "notification", send: func(t *testing.T, c *Conn) error {
+			return c.Notify(context.Background(), "failed", nil)
+		}},
+		{name: "reply", send: func(t *testing.T, c *Conn) error {
+			return c.Reply(context.Background(), ID{}, nil)
+		}},
+		{name: "error reply", send: func(t *testing.T, c *Conn) error {
+			return c.ReplyWithError(context.Background(), ID{}, &Error{Code: CodeInternalError})
+		}},
+		{name: "response", send: func(t *testing.T, c *Conn) error {
+			return c.SendResponse(context.Background(), &Response{ID: ID{}, Result: &jsonNull})
+		}},
+	}
+	for _, test := range tests {
+		t.Run(test.name, func(t *testing.T) {
+			stream := &writeErrorStream{closed: make(chan struct{})}
+			c := NewConn(context.Background(), stream, nil)
+			defer c.Close()
+
+			pending, err := c.DispatchCall(context.Background(), "pending", nil)
+			if err != nil {
+				t.Fatal(err)
+			}
+			stream.writeErr = errors.New("write failed")
+			for i := 0; i < 3; i++ {
+				if err := test.send(t, c); err != stream.writeErr {
+					t.Fatalf("got error %v, want %v", err, stream.writeErr)
+				}
+				c.mu.Lock()
+				count, original := len(c.pending), c.pending[ID{}]
+				c.mu.Unlock()
+				if count != 1 || original != pending.call {
+					t.Errorf("after failure %d: got %d pending calls, want only the original call", i+1, count)
+				}
+			}
+
+			stream.writeErr = nil
+			next, err := c.DispatchCall(context.Background(), "next", nil)
+			if err != nil {
+				t.Fatal(err)
+			}
+			if err := c.Close(); err != nil {
+				t.Fatal(err)
+			}
+			for _, waiter := range []Waiter{pending, next} {
+				if err := waiter.Wait(context.Background(), nil); err != ErrClosed {
+					t.Errorf("got error %v, want %v", err, ErrClosed)
+				}
+			}
+			c.mu.Lock()
+			count := len(c.pending)
+			c.mu.Unlock()
+			if count != 0 {
+				t.Errorf("got %d pending calls after close, want 0", count)
+			}
+		})
+	}
+}
+
+type writeErrorStream struct {
+	writeErr error
+	closed   chan struct{}
+}
+
+func (s *writeErrorStream) WriteObject(interface{}) error { return s.writeErr }
+
+func (s *writeErrorStream) ReadObject(interface{}) error {
+	<-s.closed
+	return io.EOF
+}
+
+func (s *writeErrorStream) Close() error {
+	close(s.closed)
+	return nil
+}