Three mechanistic pathways for the [Ind2TiMe2]-catalyzed intramolecular hydroamination of alkenes have been investigated by employing density functional theory calculations on the possible intermediates and transition states. The results indicate that the reaction cycle proceeds via a Ti–imido–amido complex as the catalytically active species. However, at the moment, the question as to whether this imido–amido complex is involved in a [2+2]-cycloaddition with the alkene or a newly proposed insertion of the alkene into a TiN single bond cannot be answered; the calculated barriers of both the insertion mechanism and the [2+2]-cycloaddition mechanism are similar (143 vs. 136 kJ mol−1), and both pathways are in accordance with the experimentally observed rate law (first-order dependence on the aminoalkene concentration). Interestingly, the newly proposed insertion mechanism that takes place by an insertion of the alkene moiety into the TiN single bond of an imido–amido complex seems to be much more likely than a mechanism that involves an alkene insertion into a TiN single bond of a corresponding trisamide. The latter mechanism, which has been proposed in analogy to rare-earth-metal-catalyzed hydroamination reactions, can be ruled out for two reasons: a surprisingly high activation barrier (164 kJ mol−1) and the fact that the rate-limiting insertion step is independent of the aminoalkene concentration. This is in sharp contrast to the experimental findings for indenyltitanium catalysts.