diff --git a/agent/agent.go b/agent/agent.go
index e614a28c8905c..33f3c5d16d493 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -844,6 +844,7 @@ func (a *agent) init(ctx context.Context) {
 				_ = session.Exit(MagicSessionErrorCode)
 				return
 			}
+			_ = session.Exit(0)
 		},
 		HostSigners: []ssh.Signer{randomSigner},
 		LocalPortForwardingCallback: func(ctx ssh.Context, destinationHost string, destinationPort uint32) bool {
@@ -1100,7 +1101,9 @@ func (a *agent) handleSSHSession(session ssh.Session) (retErr error) {
 		if err != nil {
 			return xerrors.Errorf("start command: %w", err)
 		}
+		var wg sync.WaitGroup
 		defer func() {
+			defer wg.Wait()
 			closeErr := ptty.Close()
 			if closeErr != nil {
 				a.logger.Warn(ctx, "failed to close tty", slog.Error(closeErr))
@@ -1117,10 +1120,16 @@ func (a *agent) handleSSHSession(session ssh.Session) (retErr error) {
 				}
 			}
 		}()
+		// We don't add input copy to wait group because
+		// it won't return until the session is closed.
 		go func() {
 			_, _ = io.Copy(ptty.Input(), session)
 		}()
+		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())
 		}()
 		err = process.Wait()
diff --git a/agent/agent_test.go b/agent/agent_test.go
index d163d7bf60dd2..c40980f5dc647 100644
--- a/agent/agent_test.go
+++ b/agent/agent_test.go
@@ -348,6 +348,57 @@ func TestAgent_Session_TTY_Hushlogin(t *testing.T) {
 	require.NotContains(t, stdout.String(), wantNotMOTD, "should not show motd")
 }
 
+func TestAgent_Session_TTY_FastCommandHasOutput(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.")
+	}
+
+	// This test is here to prevent regressions where quickly executing
+	// commands (with TTY) don't flush their output to the SSH session.
+	//
+	// See: https://github.com/coder/coder/issues/6656
+	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 1000 iterations is basically a guaranteed failure (but let's
+	// not increase test times needlessly).
+	for i := 0; i < 5; 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()
+			err = session.Start("echo wazzup")
+			require.NoError(t, err)
+
+			err = session.Wait()
+			require.NoError(t, err)
+			require.Contains(t, stdout.String(), "wazzup", "should output greeting")
+		}()
+	}
+}
+
 //nolint:paralleltest // This test reserves a port.
 func TestAgent_TCPLocalForwarding(t *testing.T) {
 	random, err := net.Listen("tcp", "127.0.0.1:0")