Does any sutta talk about the right conditions for teaching the Dhamma? I've read in other posts (such as this one) about the right way to teach the Dhamma.

But is there a way to know about the "when", i.e. when to reach out someone else to teach the Dhamma?

In specific, I'd like to know if one should teach only when asked for it, or if one should make assumptions about the other's needs or degree of knowledge when trying to help him/her (regardless if that person asked for that helped or not).

If you could provide information about suttas where this is talked about, I'd really appreaciate it. I'd even be grateful if personal experiences are given.

Thanks for your time and patience!
Part Three: The 16 Dealing with Teaching Dhamma
57. I will not teach Dhamma to a person with an umbrella in his hand who is not ill: a training to be observed.


I will not teach Dhamma to a person with a staff in his hand who is not ill: a training to be observed.
I will not teach Dhamma to a person with a knife in his hand who is not ill: a training to be observed.
I will not teach Dhamma to a person with a weapon in his hand who is not ill: a training to be observed.
[62.] I will not teach Dhamma to a person wearing non-leather [leather] footwear who is not ill: a training to be observed.
I will not teach Dhamma to a person in a vehicle who is not ill: a training to be observed.
I will not teach Dhamma to a person lying down who is not ill: a training to be observed.
I will not teach Dhamma to a person who sits clasping his knees and who is not ill: a training to be observed.
I will not teach Dhamma to a person wearing headgear who is not ill: a training to be observed.
I will not teach Dhamma to a person whose head is covered (with a robe or scarf) and who is not ill: a training to be observed.
Sitting on the ground, I will not teach Dhamma to a person sitting on a seat who is not ill: a training to be observed.
Sitting on a low seat, I will not teach Dhamma to a person sitting on a high seat who is not ill: a training to be observed.
Standing, I will not teach Dhamma to a person sitting who is not ill: a training to be observed.
Walking behind, I will not teach Dhamma to a person walking ahead who is not ill: a training to be observed.
Walking beside a path, I will not teach Dhamma to a person walking on the path who is not ill: a training to be observed.


https://www.accesstoinsight.org/tipitaka/vin/sv/bhikkhu-pati.html