diff --git a/imapclient/connection_test.go b/imapclient/connection_test.go
new file mode 100644
index 00000000..d7bb2730
--- /dev/null
+++ b/imapclient/connection_test.go
@@ -0,0 +1,154 @@
+package imapclient_test
+
+import (
+	"io"
+	"net"
+	"testing"
+	"time"
+
+	"github.com/emersion/go-imap/v2/imapclient"
+)
+
+type pipeConn struct {
+	io.Reader
+	io.Writer
+	closer io.Closer
+}
+
+func (c pipeConn) Close() error {
+	return c.closer.Close()
+}
+
+func (c pipeConn) LocalAddr() net.Addr {
+	return &net.TCPAddr{IP: net.IPv4(127, 0, 0, 1), Port: 0}
+}
+
+func (c pipeConn) RemoteAddr() net.Addr {
+	return &net.TCPAddr{IP: net.IPv4(127, 0, 0, 1), Port: 0}
+}
+
+func (c pipeConn) SetDeadline(t time.Time) error {
+	return nil
+}
+
+func (c pipeConn) SetReadDeadline(t time.Time) error {
+	return nil
+}
+
+func (c pipeConn) SetWriteDeadline(t time.Time) error {
+	return nil
+}
+
+var _ net.Conn = pipeConn{}
+
+// TestCommand_Wait_ConnectionFailure tests that Wait() returns an error instead
+// of hanging when the network connection drops unexpectedly.
+func TestCommand_Wait_ConnectionFailure(t *testing.T) {
+	// Create a custom connection pair
+	clientR, serverW := io.Pipe()
+	serverR, clientW := io.Pipe()
+
+	clientConn := pipeConn{
+		Reader: clientR,
+		Writer: clientW,
+		closer: clientW,
+	}
+	serverConn := pipeConn{
+		Reader: serverR,
+		Writer: serverW,
+		closer: serverW,
+	}
+
+	client := imapclient.New(clientConn, nil)
+	defer client.Close()
+
+	// Hacky server which sends greeting then closes without responding to commands.
+	go func() {
+		serverW.Write([]byte("* OK IMAP server ready\r\n"))
+
+		buf := make([]byte, 1024)
+		serverR.Read(buf)
+
+		time.Sleep(50 * time.Millisecond)
+		serverConn.Close()
+	}()
+
+	if err := client.WaitGreeting(); err != nil {
+		t.Fatalf("WaitGreeting() = %v", err)
+	}
+
+	noopCmd := client.Noop()
+
+	// Wait should return an error, not hang
+	errCh := make(chan error, 1)
+	go func() {
+		errCh <- noopCmd.Wait()
+	}()
+
+	select {
+	case err := <-errCh:
+		if err == nil {
+			t.Error("Expected error after connection failure, got nil")
+		} else {
+			t.Logf("Wait() returned error as expected: %v", err)
+		}
+	case <-time.After(2 * time.Second):
+		t.Fatal("Wait() hung after connection failure")
+	}
+}
+
+// TestMultipleCommands_ConnectionFailure tests that multiple pending commands
+// are properly unblocked when the connection drops.
+func TestMultipleCommands_ConnectionFailure(t *testing.T) {
+	// Create a custom connection pair
+	clientR, serverW := io.Pipe()
+	serverR, clientW := io.Pipe()
+
+	clientConn := pipeConn{
+		Reader: clientR,
+		Writer: clientW,
+		closer: clientW,
+	}
+	serverConn := pipeConn{
+		Reader: serverR,
+		Writer: serverW,
+		closer: serverW,
+	}
+
+	client := imapclient.New(clientConn, nil)
+	defer client.Close()
+
+	// Hacky server which send greeting then closes without responding.
+	go func() {
+		serverW.Write([]byte("* OK IMAP server ready\r\n"))
+
+		buf := make([]byte, 4096)
+		serverR.Read(buf)
+
+		time.Sleep(100 * time.Millisecond)
+		serverConn.Close()
+	}()
+
+	if err := client.WaitGreeting(); err != nil {
+		t.Fatalf("WaitGreeting() = %v", err)
+	}
+
+	cmd1 := client.Noop()
+	cmd2 := client.Noop()
+	cmd3 := client.Noop()
+
+	done := make(chan struct{})
+	go func() {
+		cmd1.Wait()
+		cmd2.Wait()
+		cmd3.Wait()
+		close(done)
+	}()
+
+	select {
+	case <-done:
+		t.Log("All commands completed after connection failure")
+	case <-time.After(5 * time.Second):
+		t.Fatal("Commands hung after connection failure")
+	}
+}