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Hi,
I am in a situation of short fall of 16 days to apply my ILR application and my dependants has to complete another 6 months to eligible for ILR.

So, my worry here is what are the options I have to apply ILR for myself and my dependants for tier2 extension for one year/6months ?

Here are my dates
Visa Start vignette - 25/June/2019
Visa End Date - 14/May/2024

Dependant
Visa Start vignette - 21/Jan/2020
Visa End Date - 14/May/2024

So, according to the dates I am in shortfall of 16 days to apply ILR.

Please advice !

For you the shortfall does not matter. Apply early and delay the biometrics.

See: How to apply early and benefit from the date of the ILR decision ?

The dependants will need a new 3 year extension under skilled worker route