diff --git a/src/runtime/webcore/ByteStream.rs b/src/runtime/webcore/ByteStream.rs
index f873f3b231b0..189d49f752ed 100644
--- a/src/runtime/webcore/ByteStream.rs
+++ b/src/runtime/webcore/ByteStream.rs
@@ -673,11 +673,24 @@ impl ByteStream {
     }
 
     pub(crate) fn drain(&self) -> Vec<u8> {
-        if !self.buffer.get().is_empty() {
+        if self.buffer.get().is_empty() {
+            return Vec::<u8>::default();
+        }
+        // Empty first so a producer.on_ready that checks `buffer.len()` sees it
+        // drained. RewriterPipe is the one producer whose on_ready feeds
+        // synchronously; when a sink is installed the native-sink wiring caller
+        // writes `drained` to it afterward, so waking the rewriter here would
+        // let it reach the sink first. Async producers only schedule work.
+        let drained = Vec::<u8>::move_from_list(self.buffer.replace(Vec::new()));
+        let sync_behind_sink = self.sink.get().is_some()
+            && matches!(
+                self.parent_const().producer.get(),
+                streams::SourceHandle::HTMLRewriter(_)
+            );
+        if !sync_behind_sink {
             self.signal_drained();
-            return Vec::<u8>::move_from_list(self.buffer.replace(Vec::new()));
         }
-        Vec::<u8>::default()
+        drained
     }
 
     /// Take a pre-attach `StreamResult::Err` stashed by [`Self::append`].
diff --git a/test/js/workerd/html-rewriter.test.js b/test/js/workerd/html-rewriter.test.js
index a6380cd1e85f..f5edd7771941 100644
--- a/test/js/workerd/html-rewriter.test.js
+++ b/test/js/workerd/html-rewriter.test.js
@@ -1741,6 +1741,71 @@ const payloads = [
   },
 ];
 
+// TextEncoderStream → HTMLRewriter → CompressionStream: the rewriter's input is
+// driven by the native-sink bypass (encodeIntoSink), and its output ByteStream
+// is consumed by a JS reader (pipeThrough), so its `drain()` is what wakes the
+// rewriter once a batch of output bytes has been taken. With enough elements
+// that one input chunk's output exceeds the rewriter's output high-water mark,
+// the rewriter's `write` returns Backpressure; this must eventually resolve.
+describe("output consumed via pipeThrough after a native-sink input transform", () => {
+  // ~50 elements → ~800 bytes of rewriter output per input chunk, well above
+  // the default output high-water mark (256).
+  const unit = "<p>abc</p>";
+  const chunk = Buffer.alloc(50 * unit.length, unit).toString();
+  const expected = Buffer.alloc(50 * 16, '<p x="1">abc</p>').toString();
+
+  // The pull() macrotask yield is load-bearing: a synchronous pull lets the
+  // rewrite drain into the pre-stream output_buffer before the downstream
+  // reader attaches, so the ByteStream drain() path under test is never hit.
+  function makeRewritten(chunks = [chunk]) {
+    let i = 0;
+    const body = new ReadableStream({
+      async pull(c) {
+        await Bun.sleep(0);
+        if (i < chunks.length) c.enqueue(chunks[i++]);
+        else c.close();
+      },
+    });
+    return new HTMLRewriter()
+      .on("p", { element: e => e.setAttribute("x", "1") })
+      .transform(new Response(body.pipeThrough(new TextEncoderStream())));
+  }
+
+  it("completes when read with arrayBuffer()", async () => {
+    const compressed = makeRewritten().body.pipeThrough(new CompressionStream("gzip"));
+    const buf = await new Response(compressed).arrayBuffer();
+    const text = await new Response(new Blob([buf]).stream().pipeThrough(new DecompressionStream("gzip"))).text();
+    expect(text).toBe(expected);
+  });
+
+  it("completes when served over HTTP", async () => {
+    await using server = Bun.serve({
+      port: 0,
+      fetch: () => new Response(makeRewritten().body.pipeThrough(new CompressionStream("gzip"))),
+    });
+    const buf = await (await fetch(server.url)).arrayBuffer();
+    const text = await new Response(new Blob([buf]).stream().pipeThrough(new DecompressionStream("gzip"))).text();
+    expect(text).toBe(expected);
+  });
+
+  // CompressionStream is the only native-byte-transform that can sit downstream
+  // of the rewriter's ByteStream output; cover each format so a later per-codec
+  // regression shows up here.
+  it.each(["gzip", "deflate", "deflate-raw", "brotli", "zstd"])("completes for CompressionStream(%s)", async format => {
+    const compressed = makeRewritten().body.pipeThrough(new CompressionStream(format));
+    const text = await new Response(compressed.pipeThrough(new DecompressionStream(format))).text();
+    expect(text).toBe(expected);
+  });
+
+  // Two input chunks → the second chunk is what the Backpressure wake must
+  // re-pull from upstream (the single-chunk case only owes the end() call).
+  it("completes across multiple input chunks", async () => {
+    const compressed = makeRewritten([chunk, chunk]).body.pipeThrough(new CompressionStream("gzip"));
+    const text = await new Response(compressed.pipeThrough(new DecompressionStream("gzip"))).text();
+    expect(text).toBe(expected + expected);
+  });
+});
+
 payloads.forEach(type => {
   type.test(`works with payload of type ${type.name}`, async () => {
     let calls = 0;