Switching from Leave to Enter to PBS Tier 2 Dependent

[N5iam]

Hi all, I have a question which came to mind by 2 immigration officers at the boarder control.

I am on tier 2 general and due to apply for ILR from mid October 2017. My wife an I had a baby last May which was born in the States (american citizen). After the baby was born, we came back to the UK with the intention to stay for a week then go back and apply for a tier 2 dependent visa from abroad. However, the immigration officer stamped our daughter with a "Leave to Enter" Stamp valid for six months and told us she should not leave the country until she sorts out her Tier 2 dependent visa which sounded a bit weird as I understand we should apply form abroad for her. Anyway, we thought it was a mistake and left the country to apply for the tier 2 depended from abroad but we had to cut the trip short and come back to the UK and didn't manage to apply.

This time when entering, the immigration officer said they gave us the "Leave to Enter" permission to allow us to apply for our new born but we did not follow the instruction and left the country without applying. They made a fuss about it but ended up giving us another "Leave to Enter" stamp for six months and again said we should apply for switch our daughter's permission as soon as possible and not leave the country again before she is granted the right permission.

Now, this came from 2 immigration officers and they asked us not to leave the country until we switch her to a depended visa. My daughter in now 2 months old. So the question is;
1. Can we apply for her to switch to tier 2 dependent from her current "leave to enter" stamp in country? Or do we need to leave the country and apply from abroad?
2. Since 6 months is more than enough for me to get my ILR. Can I wait until I get my ILR and apply for ILR for the new born at the same time instead? To my understanding, residency requirement does not apply for depended children. If yes, Can we apply in country?
3. Shall I wait until I get my ILR and apply for a settled person dependent visa for my daughter straight away? If yes, can we apply in country?
4. Any other options or recommendations?

Hope you will be able to help. It will be much appreciated.

Cheers,

[N5iam]

So anyone can help here? Will be much appreciated.

[Casa]

As your child was born outside of the UK they will follow the immigration path of the least privileged parent. When will your spouse qualify for ILR?

[N5iam]

Hi Casa, thank you for getting back to me. My wife qualifies for ILR from May 2021.

Do you think I can apply for my child's tier2 dependent visa from in country with the 6 months "Leave to Enter" stamp?