diff --git a/e2e/tests/machineprovider/testdata/machineprovider/provider.yaml b/e2e/tests/machineprovider/testdata/machineprovider/provider.yaml
index 23dcd28be..aac71c23c 100644
--- a/e2e/tests/machineprovider/testdata/machineprovider/provider.yaml
+++ b/e2e/tests/machineprovider/testdata/machineprovider/provider.yaml
@@ -5,10 +5,14 @@ description: |-
 options:
   LOCATION:
     description: The location Devsy should use
+  INACTIVITY_TIMEOUT:
+    description: The timeout until the machine will be stopped
+    default: 30s
 agent:
   local: true
   docker:
     install: false
+  inactivityTimeout: ${INACTIVITY_TIMEOUT}
 exec:
   create: |-
     mkdir -p ${LOCATION}/${MACHINE_ID}
diff --git a/pkg/inject/inject.go b/pkg/inject/inject.go
index f5517be11..f1785fdb8 100644
--- a/pkg/inject/inject.go
+++ b/pkg/inject/inject.go
@@ -305,26 +305,50 @@ func readLine(reader io.Reader) (string, error) {
 	}
 }
 
+const pipeSecondDirTimeout = 5 * time.Second
+
 func pipe(
 	toStdin io.WriteCloser, fromStdin io.Reader,
 	toStdout io.Writer, fromStdout io.ReadCloser,
 ) error {
-	errChan := make(chan error, 2)
+	stdinErr := make(chan error, 1)
+	stdoutErr := make(chan error, 1)
+
 	go func() {
 		_, err := io.Copy(toStdout, fromStdout)
-		errChan <- err
+		stdoutErr <- err
 	}()
 	go func() {
 		_, err := io.Copy(toStdin, fromStdin)
-		errChan <- err
+		stdinErr <- err
 	}()
 
-	first := <-errChan
+	// Wait for whichever direction completes first.
+	var firstErr error
+	var otherCh <-chan error
+	select {
+	case firstErr = <-stdinErr:
+		otherCh = stdoutErr
+	case firstErr = <-stdoutErr:
+		otherCh = stdinErr
+	}
+
+	// Give the other direction time to finish naturally so we can
+	// capture any real error and avoid interrupting data in flight.
+	// If it doesn't finish in time, close pipes to force completion.
+	var secondErr error
+	timer := time.NewTimer(pipeSecondDirTimeout)
+	defer timer.Stop()
+	select {
+	case secondErr = <-otherCh:
+	case <-timer.C:
+	}
 
 	_ = toStdin.Close()
 	_ = fromStdout.Close()
 
-	<-errChan
-
-	return first
+	if firstErr != nil {
+		return firstErr
+	}
+	return secondErr
 }
diff --git a/pkg/inject/inject_test.go b/pkg/inject/inject_test.go
index 845627d0f..848254f25 100644
--- a/pkg/inject/inject_test.go
+++ b/pkg/inject/inject_test.go
@@ -4,6 +4,7 @@ import (
 	"bytes"
 	"context"
 	"errors"
+	"fmt"
 	"io"
 	"os"
 	"runtime"
@@ -153,6 +154,39 @@ func (s *PipeTestSuite) TestPipe_NoGoroutineLeak() {
 	s.LessOrEqual(after, before+5, "goroutine leak detected: before=%d after=%d", before, after)
 }
 
+func (s *PipeTestSuite) TestPipe_ConcurrentCopyRaceRegression() {
+	for i := range 100 {
+		func() {
+			fromStdinReader, fromStdinWriter := io.Pipe()
+			toStdoutBuf := &bytes.Buffer{}
+
+			fromStdoutReader, fromStdoutWriter := io.Pipe()
+			toStdinPipeReader, toStdinPipeWriter := io.Pipe()
+
+			errCh := make(chan error, 1)
+			go func() {
+				errCh <- pipe(toStdinPipeWriter, fromStdinReader, toStdoutBuf, fromStdoutReader)
+			}()
+
+			msg := fmt.Sprintf("iteration-%d", i)
+			_, err := fromStdinWriter.Write([]byte(msg))
+			s.Require().NoError(err)
+			_ = fromStdinWriter.Close()
+
+			_, err = fromStdoutWriter.Write([]byte(msg))
+			s.Require().NoError(err)
+			_ = fromStdoutWriter.Close()
+
+			received, err := io.ReadAll(toStdinPipeReader)
+			s.Require().NoError(err)
+
+			s.NoError(<-errCh)
+			s.Equal(msg, string(received), "stdin data lost at iteration %d", i)
+			s.Equal(msg, toStdoutBuf.String(), "stdout data lost at iteration %d", i)
+		}()
+	}
+}
+
 func TestPipeSuite(t *testing.T) {
 	suite.Run(t, new(PipeTestSuite))
 }