If that's a shot of your TM, it's working. TM purges old data to make room and if you try and go back into a purged period, you won't be able to.
It's also possible that TM stopped backing up so long ago that period was never backed up. Or you may have erased the drive and forgot, or replaced an old drive with a new one, the drive is failing ....
Have you confirmed recent data is in fact being backed up?
I've been updating every chance I get on 5 Macs since 2015. At no time did a new version of the OS cause a problem with TM. That's not to say it can't I guess, just it hasn't for me an any of our friends that I know of.