When to issue section 21 when going from fixed term to rolling agreement

The current tenancy is 10 days away from expiring. The tenant has not committed to the proposed new tenancy nor has he expressed he intends to leave at the end of the tenancy. I understand the default position will be that the tenancy will migrate to a rolling tenancy under the same terms as the previous AST.
As the tenant is being non-commital I intend to issue a section 21 to vacate the property for which I need to give 2 months notice. Can I specify the date to vacate as 2 months from now i.e. to vacate 7 weeks into the rolling period?

Secondly, if after issuing the Section 21 he decides he does want to enter into a new AST will that automatically cancel out the S21 or is another formality required?

Why? Its better for the landlord to have tenants on a periodic tenancy. The terms are the same as during the fixed term except that either party can serve notice if circumstances change.

I have been on this forum for a few months now and it appears that there are a few Landlords that look to renew tenancy agreements as they expire. In your case you intend to serve a s21 just because your tenant hasn’t committed to a new tenancy. This is poor practice! I prefer to let the tenancy roll onto a periodic, it’s less work. The additional admin associated with serving a s21, and then advertising for a new tenant and then serving all the documents associated with the new tenancy not to mention the souring of the landlord/tenant relationship. If you already have a good tenant that pays their rent on time and is looking after your property, why serve them with an eviction notice? In this climate if a tenant serves notice to leave, a landlord should be able to easily replace that tenant. After the fixed term, if you need to raise the rent then do so. If the tenant doesn’t want to pay or can’t afford it then you have a justifiable reason to serve a s21. You should look to review this practice because s21 will be abolished by the end of the year.

I’m with Chris and David122