diff --git a/Cargo.toml b/Cargo.toml
index fbf3f11..e6422d9 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -55,6 +55,8 @@ proptest-derive = "0.5"
 rand = "0.8.5"
 tokio = { version = "1.24.2", default-features = false, features = ["io-util", "macros", "rt-multi-thread", "io-std"] }
 tokio-util = { version = "0.7", default-features = false, features = ["io"] }
+tracing = "0.1.40"
+tracing-subscriber = "0.3.18"
 
 [[test]]
 name = "brotli"
diff --git a/src/tokio/write/generic/encoder.rs b/src/tokio/write/generic/encoder.rs
index f5a83aa..c26dc24 100644
--- a/src/tokio/write/generic/encoder.rs
+++ b/src/tokio/write/generic/encoder.rs
@@ -13,20 +13,13 @@ use futures_core::ready;
 use pin_project_lite::pin_project;
 use tokio::io::{AsyncBufRead, AsyncRead, AsyncWrite, ReadBuf};
 
-#[derive(Debug)]
-enum State {
-    Encoding,
-    Finishing,
-    Done,
-}
-
 pin_project! {
     #[derive(Debug)]
     pub struct Encoder<W, E> {
         #[pin]
         writer: BufWriter<W>,
         encoder: E,
-        state: State,
+        finished: bool
     }
 }
 
@@ -35,7 +28,7 @@ impl<W: AsyncWrite, E: Encode> Encoder<W, E> {
         Self {
             writer: BufWriter::new(writer),
             encoder,
-            state: State::Encoding,
+            finished: false,
         }
     }
 }
@@ -62,97 +55,6 @@ impl<W, E> Encoder<W, E> {
     }
 }
 
-impl<W: AsyncWrite, E: Encode> Encoder<W, E> {
-    fn do_poll_write(
-        self: Pin<&mut Self>,
-        cx: &mut Context<'_>,
-        input: &mut PartialBuffer<&[u8]>,
-    ) -> Poll<io::Result<()>> {
-        let mut this = self.project();
-
-        loop {
-            let output = ready!(this.writer.as_mut().poll_partial_flush_buf(cx))?;
-            let mut output = PartialBuffer::new(output);
-
-            *this.state = match this.state {
-                State::Encoding => {
-                    this.encoder.encode(input, &mut output)?;
-                    State::Encoding
-                }
-
-                State::Finishing | State::Done => {
-                    return Poll::Ready(Err(io::Error::new(
-                        io::ErrorKind::Other,
-                        "Write after shutdown",
-                    )))
-                }
-            };
-
-            let produced = output.written().len();
-            this.writer.as_mut().produce(produced);
-
-            if input.unwritten().is_empty() {
-                return Poll::Ready(Ok(()));
-            }
-        }
-    }
-
-    fn do_poll_flush(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<io::Result<()>> {
-        let mut this = self.project();
-
-        loop {
-            let output = ready!(this.writer.as_mut().poll_partial_flush_buf(cx))?;
-            let mut output = PartialBuffer::new(output);
-
-            let done = match this.state {
-                State::Encoding => this.encoder.flush(&mut output)?,
-
-                State::Finishing | State::Done => {
-                    return Poll::Ready(Err(io::Error::new(
-                        io::ErrorKind::Other,
-                        "Flush after shutdown",
-                    )))
-                }
-            };
-
-            let produced = output.written().len();
-            this.writer.as_mut().produce(produced);
-
-            if done {
-                return Poll::Ready(Ok(()));
-            }
-        }
-    }
-
-    fn do_poll_shutdown(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<io::Result<()>> {
-        let mut this = self.project();
-
-        loop {
-            let output = ready!(this.writer.as_mut().poll_partial_flush_buf(cx))?;
-            let mut output = PartialBuffer::new(output);
-
-            *this.state = match this.state {
-                State::Encoding | State::Finishing => {
-                    if this.encoder.finish(&mut output)? {
-                        State::Done
-                    } else {
-                        State::Finishing
-                    }
-                }
-
-                State::Done => State::Done,
-            };
-
-            let produced = output.written().len();
-            this.writer.as_mut().produce(produced);
-
-            if let State::Done = this.state {
-                return Poll::Ready(Ok(()));
-            }
-        }
-    }
-}
-
 impl<W: AsyncWrite, E: Encode> AsyncWrite for Encoder<W, E> {
     fn poll_write(
         self: Pin<&mut Self>,
@@ -163,24 +65,49 @@ impl<W: AsyncWrite, E: Encode> AsyncWrite for Encoder<W, E> {
             return Poll::Ready(Ok(0));
         }
 
-        let mut input = PartialBuffer::new(buf);
+        let mut this = self.project();
+
+        let mut encodeme = PartialBuffer::new(buf);
 
-        match self.do_poll_write(cx, &mut input)? {
-            Poll::Pending if input.written().is_empty() => Poll::Pending,
-            _ => Poll::Ready(Ok(input.written().len())),
+        loop {
+            let mut space =
+                PartialBuffer::new(ready!(this.writer.as_mut().poll_partial_flush_buf(cx))?);
+            this.encoder.encode(&mut encodeme, &mut space)?;
+            let bytes_encoded = space.written().len();
+            this.writer.as_mut().produce(bytes_encoded);
+            if encodeme.unwritten().is_empty() {
+                break;
+            }
         }
+
+        Poll::Ready(Ok(encodeme.written().len()))
     }
 
     fn poll_flush(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<io::Result<()>> {
-        ready!(self.as_mut().do_poll_flush(cx))?;
-        ready!(self.project().writer.as_mut().poll_flush(cx))?;
+        let mut this = self.project();
+        loop {
+            let mut space =
+                PartialBuffer::new(ready!(this.writer.as_mut().poll_partial_flush_buf(cx))?);
+            let flushed = this.encoder.flush(&mut space)?;
+            let bytes_encoded = space.written().len();
+            this.writer.as_mut().produce(bytes_encoded);
+            if flushed {
+                break;
+            }
+        }
         Poll::Ready(Ok(()))
     }
 
     fn poll_shutdown(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<io::Result<()>> {
-        ready!(self.as_mut().do_poll_shutdown(cx))?;
-        ready!(self.project().writer.as_mut().poll_shutdown(cx))?;
-        Poll::Ready(Ok(()))
+        let mut this = self.project();
+        while !*this.finished {
+            let mut space =
+                PartialBuffer::new(ready!(this.writer.as_mut().poll_partial_flush_buf(cx))?);
+            *this.finished = this.encoder.finish(&mut space)?;
+            let bytes_encoded = space.written().len();
+            this.writer.as_mut().produce(bytes_encoded);
+        }
+        this.writer.poll_shutdown(cx)
     }
 }
 
diff --git a/tests/issues.rs b/tests/issues.rs
new file mode 100644
index 0000000..3d52cd4
--- /dev/null
+++ b/tests/issues.rs
@@ -0,0 +1,153 @@
+#![cfg(all(feature = "tokio", feature = "zstd"))]
+
+use std::{
+    io,
+    pin::Pin,
+    task::{ready, Context, Poll},
+};
+
+use async_compression::tokio::write::ZstdEncoder;
+use tokio::io::{AsyncWrite, AsyncWriteExt as _};
+use tracing_subscriber::fmt::format::FmtSpan;
+
+/// This issue covers our state machine being invalid when using adapters
+/// like [`tokio_util::codec`].
+///
+/// After the first [`poll_shutdown`] call,
+/// we must expect any number of [`poll_flush`] and [`poll_shutdown`] calls,
+/// until [`poll_shutdown`] returns [`Poll::Ready`],
+/// according to the documentation on [`AsyncWrite`].
+///
+/// <https://github.com/Nullus157/async-compression/issues/246>
+///
+/// [`tokio_util::codec`](https://docs.rs/tokio-util/latest/tokio_util/codec)
+/// [`poll_shutdown`](AsyncWrite::poll_shutdown)
+/// [`poll_flush`](AsyncWrite::poll_flush)
+#[test]
+fn issue_246() {
+    tracing_subscriber::fmt()
+        .without_time()
+        .with_ansi(false)
+        .with_level(false)
+        .with_test_writer()
+        .with_target(false)
+        .with_span_events(FmtSpan::NEW)
+        .init();
+    let mut zstd_encoder = Wrapper::new(Trace::new(ZstdEncoder::new(DelayedShutdown::default())));
+    futures::executor::block_on(zstd_encoder.shutdown()).unwrap();
+}
+
+pin_project_lite::pin_project! {
+    /// A simple wrapper struct that follows the [`AsyncWrite`] protocol.
+    /// This is a stand-in for combinators like `tokio_util::codec`s
+    struct Wrapper<T> {
+        #[pin] inner: T
+    }
+}
+
+impl<T> Wrapper<T> {
+    fn new(inner: T) -> Self {
+        Self { inner }
+    }
+}
+
+impl<T: AsyncWrite> AsyncWrite for Wrapper<T> {
+    #[tracing::instrument(name = "Wrapper::poll_write", skip_all, ret)]
+    fn poll_write(
+        self: Pin<&mut Self>,
+        cx: &mut Context<'_>,
+        buf: &[u8],
+    ) -> Poll<Result<usize, io::Error>> {
+        self.project().inner.poll_write(cx, buf)
+    }
+
+    #[tracing::instrument(name = "Wrapper::poll_flush", skip_all, ret)]
+    fn poll_flush(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Result<(), io::Error>> {
+        self.project().inner.poll_flush(cx)
+    }
+
+    /// To quote the [`AsyncWrite`] docs:
+    /// > Invocation of a shutdown implies an invocation of flush.
+    /// > Once this method returns Ready it implies that a flush successfully happened before the shutdown happened.
+    /// > That is, callers don't need to call flush before calling shutdown.
+    /// > They can rely that by calling shutdown any pending buffered data will be written out.
+    #[tracing::instrument(name = "Wrapper::poll_shutdown", skip_all, ret)]
+    fn poll_shutdown(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Result<(), io::Error>> {
+        let mut this = self.project();
+        ready!(this.inner.as_mut().poll_flush(cx))?;
+        this.inner.poll_shutdown(cx)
+    }
+}
+
+pin_project_lite::pin_project! {
+    /// Yields [`Poll::Pending`] the first time [`AsyncWrite::poll_shutdown`] is called.
+    #[derive(Default)]
+    struct DelayedShutdown {
+        contents: Vec<u8>,
+        num_times_shutdown_called: u8,
+    }
+}
+
+impl AsyncWrite for DelayedShutdown {
+    #[tracing::instrument(name = "DelayedShutdown::poll_write", skip_all, ret)]
+    fn poll_write(
+        self: Pin<&mut Self>,
+        cx: &mut Context<'_>,
+        buf: &[u8],
+    ) -> Poll<Result<usize, io::Error>> {
+        let _ = cx;
+        self.project().contents.extend_from_slice(buf);
+        Poll::Ready(Ok(buf.len()))
+    }
+
+    #[tracing::instrument(name = "DelayedShutdown::poll_flush", skip_all, ret)]
+    fn poll_flush(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Result<(), io::Error>> {
+        let _ = cx;
+        Poll::Ready(Ok(()))
+    }
+
+    #[tracing::instrument(name = "DelayedShutdown::poll_shutdown", skip_all, ret)]
+    fn poll_shutdown(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Result<(), io::Error>> {
+        match self.project().num_times_shutdown_called {
+            it @ 0 => {
+                *it += 1;
+                cx.waker().wake_by_ref();
+                Poll::Pending
+            }
+            _ => Poll::Ready(Ok(())),
+        }
+    }
+}
+
+pin_project_lite::pin_project! {
+    /// A wrapper which traces all calls
+    struct Trace<T> {
+        #[pin] inner: T
+    }
+}
+
+impl<T> Trace<T> {
+    fn new(inner: T) -> Self {
+        Self { inner }
+    }
+}
+
+impl<T: AsyncWrite> AsyncWrite for Trace<T> {
+    #[tracing::instrument(name = "Trace::poll_write", skip_all, ret)]
+    fn poll_write(
+        self: Pin<&mut Self>,
+        cx: &mut Context<'_>,
+        buf: &[u8],
+    ) -> Poll<Result<usize, io::Error>> {
+        self.project().inner.poll_write(cx, buf)
+    }
+    #[tracing::instrument(name = "Trace::poll_flush", skip_all, ret)]
+    fn poll_flush(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Result<(), io::Error>> {
+        self.project().inner.poll_flush(cx)
+    }
+
+    #[tracing::instrument(name = "Trace::poll_shutdown", skip_all, ret)]
+    fn poll_shutdown(self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Result<(), io::Error>> {
+        self.project().inner.poll_shutdown(cx)
+    }
+}