Off-Site drives are always over filling

What's a network drive - your backup destination?

You would need to contact customer support to check to see if you are entitled to a free upgrade or not:

https://support.symantec.com/en_US/contact-us.html

Yes, the three drives are on the network. Meaning they have an IP address and are not physically connected to the server. 

Then I'm a bit confused. Earlier you mentioned that you are rotating drives.

How exactly does that work when you are using network drives...?

It's all discussed here on how I have it setup near the bottom of the comments between you and I. https://www-secure.symantec.com/connect/forums/ssr-2013-site-site-different-file-sizes

But basically we have three drives, 1 on-site and 2 off-site.

X.X.X.40 is the on-site

X.X.X.41 is off-site drive A

X.X.X.42 is off-site drive B

Drive A is on the network for a full week and then on Friday before people leave for the work drive A and B are swapped. 

I just upgraded to R2 on a server and ran a backup. It did not remove older files on the off-site drive.

I think the damage may have already been done. If possible, can you start with a 'clean slate' now that you have upgraded? I know this is far from ideal, but this is the only way of us knowing if things are working smoothly with R2.

So ideally remove your backup job and re-create it. Specify a new backup destination folder (so if needed, move your most recent backup set to another location if you need to free up space).

By the way, it seems you are using network shares as your offsite location. What exactly are these shares hosted on (i.e. what is the underlying hardware)?

Are you saying I should delete on-site and off-site drive data from the previous backup created in SSR 2013?

The shares are just on an external network drive that is plugged into the network. This is the drive: https://www.lacie.com/us/products/product.htm?id=10476

Yes, basically starting from nothing (again, sorry, I know this is not ideal). Obviously don't delete your backups until you have a new good backup (move to alternate location rather than delete).

Maybe set the schedule to start a new base/set to weekly for now. That way we'll know within a week whether or not this is working.... rather than waiting for a month.

Ok. I'll do it on one server for now and go from there.

Just checking to see if there are any updates on this?

So far so good. I'll try the file server next. That has more changes in it than the Management server.