diff --git a/agent/agent.go b/agent/agent.go
index 33f3c5d16d493..1efb3e88f3dbe 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -1125,13 +1125,28 @@ func (a *agent) handleSSHSession(session ssh.Session) (retErr error) {
 		go func() {
 			_, _ = io.Copy(ptty.Input(), session)
 		}()
+
+		// In low parallelism scenarios, the command may exit and we may close
+		// the pty before the output copy has started. This can result in the
+		// output being lost. To avoid this, we wait for the output copy to
+		// start before waiting for the command to exit. This ensures that the
+		// output copy goroutine will be scheduled before calling close on the
+		// pty. There is still a risk of data loss if a command produces a lot
+		// of output, see TestAgent_Session_TTY_HugeOutputIsNotLost (skipped).
+		outputCopyStarted := make(chan struct{})
+		ptyOutput := func() io.Reader {
+			defer close(outputCopyStarted)
+			return ptty.Output()
+		}
 		wg.Add(1)
 		go func() {
 			// Ensure data is flushed to session on command exit, if we
 			// close the session too soon, we might lose data.
 			defer wg.Done()
-			_, _ = io.Copy(session, ptty.Output())
+			_, _ = io.Copy(session, ptyOutput())
 		}()
+		<-outputCopyStarted
+
 		err = process.Wait()
 		var exitErr *exec.ExitError
 		// ExitErrors just mean the command we run returned a non-zero exit code, which is normal
diff --git a/agent/agent_test.go b/agent/agent_test.go
index c40980f5dc647..10ccbe51242a8 100644
--- a/agent/agent_test.go
+++ b/agent/agent_test.go
@@ -373,9 +373,12 @@ func TestAgent_Session_TTY_FastCommandHasOutput(t *testing.T) {
 
 	var stdout bytes.Buffer
 	// NOTE(mafredri): Increase iterations to increase chance of failure,
-	//                 assuming bug is present.
+	//                 assuming bug is present. Limiting GOMAXPROCS further
+	//                 increases the chance of failure.
 	// Using 1000 iterations is basically a guaranteed failure (but let's
 	// not increase test times needlessly).
+	// Limit GOMAXPROCS (e.g. `export GOMAXPROCS=1`) to further increase
+	// chance of failure. Also -race helps.
 	for i := 0; i < 5; i++ {
 		func() {
 			stdout.Reset()
@@ -399,6 +402,63 @@ func TestAgent_Session_TTY_FastCommandHasOutput(t *testing.T) {
 	}
 }
 
+func TestAgent_Session_TTY_HugeOutputIsNotLost(t *testing.T) {
+	t.Parallel()
+	if runtime.GOOS == "windows" {
+		// This might be our implementation, or ConPTY itself.
+		// It's difficult to find extensive tests for it, so
+		// it seems like it could be either.
+		t.Skip("ConPTY appears to be inconsistent on Windows.")
+	}
+	t.Skip("This test proves we have a bug where parts of large output on a PTY can be lost after the command exits, skipped to avoid test failures.")
+
+	// This test is here to prevent prove we have a bug where quickly executing
+	// commands (with TTY) don't flush their output to the SSH session. This is
+	// due to the pty being closed before all the output has been copied, but
+	// protecting against this requires a non-trivial rewrite of the output
+	// processing (or figuring out a way to put the pty in a mode where this
+	// does not happen).
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+	defer cancel()
+	//nolint:dogsled
+	conn, _, _, _, _ := setupAgent(t, agentsdk.Metadata{}, 0)
+	sshClient, err := conn.SSHClient(ctx)
+	require.NoError(t, err)
+	defer sshClient.Close()
+
+	ptty := ptytest.New(t)
+
+	var stdout bytes.Buffer
+	// NOTE(mafredri): Increase iterations to increase chance of failure,
+	//                 assuming bug is present.
+	// Using 10 iterations is basically a guaranteed failure (but let's
+	// not increase test times needlessly). Run with -race and do not
+	// limit parallelism (`export GOMAXPROCS=10`) to increase the chance
+	// of failure.
+	for i := 0; i < 1; i++ {
+		func() {
+			stdout.Reset()
+
+			session, err := sshClient.NewSession()
+			require.NoError(t, err)
+			defer session.Close()
+			err = session.RequestPty("xterm", 128, 128, ssh.TerminalModes{})
+			require.NoError(t, err)
+
+			session.Stdout = &stdout
+			session.Stderr = ptty.Output()
+			session.Stdin = ptty.Input()
+			want := strings.Repeat("wazzup", 1024+1) // ~6KB, +1 because 1024 is a common buffer size.
+			err = session.Start("echo " + want)
+			require.NoError(t, err)
+
+			err = session.Wait()
+			require.NoError(t, err)
+			require.Contains(t, stdout.String(), want, "should output entire greeting")
+		}()
+	}
+}
+
 //nolint:paralleltest // This test reserves a port.
 func TestAgent_TCPLocalForwarding(t *testing.T) {
 	random, err := net.Listen("tcp", "127.0.0.1:0")