diff --git a/crates/test-programs/src/bin/cli_serve_with_print.rs b/crates/test-programs/src/bin/cli_serve_with_print.rs
new file mode 100644
index 0000000000..424eb841cf
--- /dev/null
+++ b/crates/test-programs/src/bin/cli_serve_with_print.rs
@@ -0,0 +1,30 @@
+use std::io::Write;
+use test_programs::proxy;
+use test_programs::wasi::http::types::{
+    Fields, IncomingRequest, OutgoingResponse, ResponseOutparam,
+};
+
+struct T;
+
+proxy::export!(T);
+
+impl proxy::exports::wasi::http::incoming_handler::Guest for T {
+    fn handle(_request: IncomingRequest, outparam: ResponseOutparam) {
+        print!("this is half a print ");
+        std::io::stdout().flush().unwrap();
+        println!("to stdout");
+        println!(); // empty line
+        println!("after empty");
+
+        eprint!("this is half a print ");
+        std::io::stderr().flush().unwrap();
+        eprintln!("to stderr");
+        eprintln!(); // empty line
+        eprintln!("after empty");
+
+        let resp = OutgoingResponse::new(Fields::new());
+        ResponseOutparam::set(outparam, Ok(resp));
+    }
+}
+
+fn main() {}
diff --git a/src/commands/serve.rs b/src/commands/serve.rs
index 8a200ee093..001688ce70 100644
--- a/src/commands/serve.rs
+++ b/src/commands/serve.rs
@@ -127,15 +127,15 @@ impl ServeCommand {
 
         builder.env("REQUEST_ID", req_id.to_string());
 
-        builder.stdout(LogStream {
-            prefix: format!("stdout [{req_id}] :: "),
-            output: Output::Stdout,
-        });
+        builder.stdout(LogStream::new(
+            format!("stdout [{req_id}] :: "),
+            Output::Stdout,
+        ));
 
-        builder.stderr(LogStream {
-            prefix: format!("stderr [{req_id}] :: "),
-            output: Output::Stderr,
-        });
+        builder.stderr(LogStream::new(
+            format!("stderr [{req_id}] :: "),
+            Output::Stderr,
+        ));
 
         let mut host = Host {
             table: wasmtime::component::ResourceTable::new(),
@@ -470,6 +470,17 @@ impl Output {
 struct LogStream {
     prefix: String,
     output: Output,
+    needs_prefix_on_next_write: bool,
+}
+
+impl LogStream {
+    fn new(prefix: String, output: Output) -> LogStream {
+        LogStream {
+            prefix,
+            output,
+            needs_prefix_on_next_write: true,
+        }
+    }
 }
 
 impl wasmtime_wasi::StdoutStream for LogStream {
@@ -489,19 +500,34 @@ impl wasmtime_wasi::StdoutStream for LogStream {
 
 impl wasmtime_wasi::HostOutputStream for LogStream {
     fn write(&mut self, bytes: bytes::Bytes) -> StreamResult<()> {
-        let mut msg = Vec::new();
-
-        for line in bytes.split(|c| *c == b'\n') {
-            if !line.is_empty() {
-                msg.extend_from_slice(&self.prefix.as_bytes());
-                msg.extend_from_slice(line);
-                msg.push(b'\n');
+        let mut bytes = &bytes[..];
+
+        while !bytes.is_empty() {
+            if self.needs_prefix_on_next_write {
+                self.output
+                    .write_all(self.prefix.as_bytes())
+                    .map_err(StreamError::LastOperationFailed)?;
+                self.needs_prefix_on_next_write = false;
+            }
+            match bytes.iter().position(|b| *b == b'\n') {
+                Some(i) => {
+                    let (a, b) = bytes.split_at(i + 1);
+                    bytes = b;
+                    self.output
+                        .write_all(a)
+                        .map_err(StreamError::LastOperationFailed)?;
+                    self.needs_prefix_on_next_write = true;
+                }
+                None => {
+                    self.output
+                        .write_all(bytes)
+                        .map_err(StreamError::LastOperationFailed)?;
+                    break;
+                }
             }
         }
 
-        self.output
-            .write_all(&msg)
-            .map_err(StreamError::LastOperationFailed)
+        Ok(())
     }
 
     fn flush(&mut self) -> StreamResult<()> {
diff --git a/tests/all/cli_tests.rs b/tests/all/cli_tests.rs
index 20078eb983..069a0e532e 100644
--- a/tests/all/cli_tests.rs
+++ b/tests/all/cli_tests.rs
@@ -1507,7 +1507,7 @@ mod test_programs {
         }
 
         /// Completes this server gracefully by printing the output on failure.
-        fn finish(mut self) -> Result<String> {
+        fn finish(mut self) -> Result<(String, String)> {
             let mut child = self.child.take().unwrap();
 
             // If the child process has already exited then collect the output
@@ -1525,7 +1525,10 @@ mod test_programs {
                 bail!("child failed {output:?}");
             }
 
-            Ok(String::from_utf8_lossy(&output.stderr).into_owned())
+            Ok((
+                String::from_utf8_lossy(&output.stdout).into_owned(),
+                String::from_utf8_lossy(&output.stderr).into_owned(),
+            ))
         }
 
         /// Send a request to this server and wait for the response.
@@ -1660,7 +1663,7 @@ mod test_programs {
             )
             .await;
         assert!(result.is_err());
-        let stderr = server.finish()?;
+        let (_, stderr) = server.finish()?;
         assert!(
             stderr.contains("maximum concurrent memory limit of 0 reached"),
             "bad stderr: {stderr}",
@@ -1766,6 +1769,51 @@ mod test_programs {
 
         Ok(())
     }
+
+    #[tokio::test]
+    async fn cli_serve_with_print() -> Result<()> {
+        let server = WasmtimeServe::new(CLI_SERVE_WITH_PRINT_COMPONENT, |cmd| {
+            cmd.arg("-Scli");
+        })?;
+
+        for _ in 0..2 {
+            let resp = server
+                .send_request(
+                    hyper::Request::builder()
+                        .uri("http://localhost/")
+                        .body(String::new())
+                        .context("failed to make request")?,
+                )
+                .await?;
+            assert!(resp.status().is_success());
+        }
+
+        let (out, err) = server.finish()?;
+        assert_eq!(
+            out,
+            "\
+stdout [0] :: this is half a print to stdout
+stdout [0] :: \n\
+stdout [0] :: after empty
+stdout [1] :: this is half a print to stdout
+stdout [1] :: \n\
+stdout [1] :: after empty
+"
+        );
+        assert_eq!(
+            err,
+            "\
+stderr [0] :: this is half a print to stderr
+stderr [0] :: \n\
+stderr [0] :: after empty
+stderr [1] :: this is half a print to stderr
+stderr [1] :: \n\
+stderr [1] :: after empty
+"
+        );
+
+        Ok(())
+    }
 }
 
 #[test]