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I am an Indian national and have been in the UK since 13th Sep 2010 under Tier 2 ICT. My visa was first issued on 27th Aug 2010. Since then I have gone through several extensions of the visa while in the UK.
Due to Covid situation, there is a situation my visa may not be extended under ICT route.

Question 1: When is the earliest date I am eligible for ILR under the long residence route?

My wife and child and have been in the UK since 6th Nov 2010 as Tier 2 ICT dependents. Their visa was first issued on 2nd Oct 2010.

Question 2: When is the earliest date my wife and child are eligible for ILR under the long residence route?

Question 3: If I am successful in my ILR application in Aug 2020, how do I ensure my dependents are eligible for ILR later this year.

From mid August 2020. You need to apply separately under SET(LR). When will your dependants visa expire?

All our visa's are currently expiring on 25th Aug 2020

You can apply for ILR no sooner than within 28 days before 13th September 2020.

Your dependents do not qualify until within 28 days before 6th November 2020 and will likely need to apply for FLR(M).

Thank you both for your replies.

What is FLR(M)?

Also assume I can apply for my ILR and FLR(M) for both my dependents in Aug.

FLR(M) is a spouse visa, valid for 2.5 years. You need to meet the English and financial requirements for this.

By switching to FLR(M) assume my wife will retain her right to work.

Yes, she has the right to do any work on FL(M) visa, no restrictions.

This is in continuation of my previous question.

My company has agreed to extend my ICT visa beyond 25th Aug 2020.
I am eligible for ILR in Sep 2020 and my dependents in Nov 2020.

Can I apply for ILR via priority same day appointment route in Sep and apply via postal route for my dependents via normal route in Nov? I am thinking of keeping the costs down.

So there will be gap of 2 months when my dependents are on a visa obtained via ICT route and I am on ILR. Will my dependents visa status be valid because as the main applicant in the ICT visa I have moved to ILR.

Can I apply for ILR via priority same day appointment route in Sep and apply via postal route for my dependents via normal route in Nov? I am thinking of keeping the costs down.

There is NO concept of 'dependent' for ILR based on long residence. EACH applicant applying for long residence ILR must meet the requirements individually.

So there will be gap of 2 months when my dependents are on a visa obtained via ICT route and I am on ILR. Will my dependents visa status be valid because as the main applicant in the ICT visa I have moved to ILR.

Why wouldn't their visas be valid??

let me put the question another way...apologies for being thick

If the main applicant switches visa type say in my case from Tier 2 ICT to ILR at a particular point in time say Sep 2020, will the dependent visas (obtained as PBS dependent) still be valid until they are eligible for ILR say in Nov 2020.

I don't want to be in a situation that because I switched to ILR, their stay becomes illegal.

If the main applicant switches visa type say in my case from Tier 2 ICT to ILR at a particular point in time say Sep 2020, will the dependent visas (obtained as PBS dependent) still be valid until they are eligible for ILR say in Nov 2020.

They would usually be required to switch to FLR(M) spouse/child visa. But as they are qualifying in their own right in November 2020, they can wait to apply for ILR, provided they do not travel out of the UK.

I don't want to be in a situation that because I switched to ILR, their stay becomes illegal.

Their visas don't just cease to exist when you get ILR. They don't become illegal.

Thank you for the quick clarification, much appreciated