Applecare for my iPad Pro

You have to initially start your Applecare+ coverage within 60 days (30 days in Japan) of original purchase; you cannot begin Applecare coverage as your warranty expires.

For those that have maintained continuous Applecare cover throughout ownership of their device, it is understood that an existing Applecare+ Plan can be extended prior to expiry of the current plan.

I think you missed that the OP's one year warranty expires April 22, 2020. They are well past the time they had to add AppleCare+ as they are way past the 60 day window of opportunity to add it.

To the OP: You had 60 days after you originally bought your iPad to add the coverage. You cannot at this point purchase AppleCare+. Sorry.

Yes, ask Apple directly, but I'm very sure you won't be given the opportunity to add it at this point.

if your iPad is still within the 60 day limit and you are runnng iPadOS 13, you can purchase additional, extended AppleCare, by going into the Settings app, under General > AppleCare, tap the gray triangle to the right side of the panel and register and pay for extended, AppleCare+ right from your iPad.

Best of Luck to You!

it is 14 days until the 20th.

Did you even try my suggestion before you replied?

Try it already!

If successful, extended AppleCare goes into effect immediately.

I guess I did not catch that the 1st year has nearly passed as implied.

I missed that or mis-understood/mis-read the OP's message.

You're welcome and good luck.

The OP still has 14 days.

I did my wife's 7th gen iPad and iPhone SE AND my Mum's iPhone 8 from the device 10 days before the 60 day period expired.