Multi-trip travel insurance renewal/claim question

[TheFungle]

I currently have an annual travel insurance policy with Virgin which fits my needs nicely, it's due to expire in May and I'd be happy to renew.

What I can't figure out is that if I book a trip September and I were to have to cancel (for an insured reason) would I be able to claim that on the existing policy?

I've asked Virgin and their response was somewhat vague.

Virgin said:

If you book a Holiday and it falls within the cover lever of you current policy then claims will be considered if you were to cancel.

[Sheepshanks]

Only if you either cancel before renewal, or renew and then cancel later.