I have recently upgraded my ArcGIS Pro to 2.5, and it seems now that I am unable to overwrite layers I have published (we update publicly available data) only getting an area that staging failed. The log says ErrorMessage: ERROR 999999: Something unexpected caused the tool to fail. Is this something anyone else is experiencing? I was able to successfully overwrite layers on a co-workers PC who is still on 2.4.
I did some more testing with 2.5. I was actually unable to publish any layers using 2.5 to our Portal or to our AGOL account. This included trying to overwrite the layers. I must have published all our layers prior to me updating.
I downgraded to 2.4 and it appears to be working fine again.
So far, 2.5 will be a no go for us.
I have not tried to open a case, but it might be something worth doing if others are experiencing it too.. It's interesting you don't have the same experience.
But clearly for me, everything is fine in 2.4, 2.5 nope...