I have a configuration question based on the following scenario:

I have a plan that expires every October 1 annually. I have some users who have plans that have expired, for example October 1, 2016.
Since we are approaching the new renewal date (October 1, 2017), I am running into situations where the expired user pays to renew but for some reason it is applying it to the current year (October 1, 2016 - September 30, 2017) rather than (October 1, 2017 - September 3- 2018).

In other words the member let the passed year go by (expired) but had decided to renew for the upcoming terms instead.

I have also set up that any memberships purchased within 3 months of the renewal date i.e July 1 - October 1) would apply to the new term

I have set the following
> "Bonus time before first period start (for calendar-based durations)" to 3 months - But I believe this is for new sign-ups
> "Renewable in advance by" 3 months
> "Grace period before real expiration" to 1 week
> "Manual renewal extends expiration date as follows" to Renewal extends date (No gap) - I think this is the one I should be looking at.

Ideally what I want to have happen is that if the user lets his/her account expire/lapse and let a term go by without renewing, and then in term 3 renews/rejoins will be paying for the upcoming terms (assuming it's within 3 months of the renewal date).

Is this possible?

There is even a situation where an expired user recently paid by the recurring payment method and were auto charged for each of the years they had let their membership expire. Their plan expired in 2014.

Ok great! I was confused by the "free" part as in the member still has access but its free, where I from you describe that free means no payment but also no access during that free period - It this correct?

So my next question is if I change the configuration of this plan with current members attached to it (expired and active) will CBSubs change for all those members or will the change only apply to newly registered members?

I just did a quick test with a "dummy" user account who is expired. After I made the change to the plan, its showing this as the renewal period:
CAD 20.00 per calendar year starting 1 October The first period for the renewal will be 1 October 2016 - 30 September 2017.

Ideally it should be 1 October 2017 - 30 September 2018 as I set the
Bonus time before first period start (for calendar-based durations) to 3 months. I'm thinking this only applies to new signups?

Is there a way to have the renewal for expired members take advantage of this bonus feature?