As we know, one way to construct a manner adverbial is using the -ing form of verbs after prepositions. However, it seems that the preposition with shows different behavior. To clarify what I mean, let us look at the following examples, using the similar preparation without:
You can answer me without a smile.
You can answer me without smiling.
But, the second example sentence in the following is incorrect:
You can answer me with a smile.
*You can answer me with smiling.
Regarding the similarity in the above examples, I wonder why it is ungrammatical with being followed by the -ing form of verbs in such a structure.