Hi, for obvious reasons it won't work with active DI boxes. I wouldn't do it with a passive one either, because passive DI boxes generally have high ratio transformers (like 12:1) witch reversed will offer a very hot output with quite a high source impedance. with a low output Z D/A converter, into a high Z guitar amp input, setting a low output level in your DAW, I guess you could somewhat make it work. you could also keep the transformer 12:1 and invert the connectors, and then set a high output level in your DAW.
Laurent.