Updating plan from monthly to yearly

Just to make sure I understand this correctly.

Yesterday, I saw Glide charging me for 1 month Private Pro subs, as I subscribed before. My main purpose was to try to see if Private Pro fit my purpose, and it did, amazingly.

Therefore, this morning I updated my plan to annually, which technically priced 360$, then I saw Glide immediately charging me not 360, but somewhat 290.

I then look at this image

So does this mean when I changed to yearly, it does not count from that moment but counts from “Yearly renewal”? And was my 40$ for 1-month also transfered to this new subscription?

Btw, if possible, I would like to have some kinds of reminder or notification before any action of charging. It wasn’t a problem but it sort of suprised me yesterday when I got the receipt. Or have we got this option already? Please show me if we did have this.

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The amounts are pro-rated.