I have to reactivate most of my channels all the time. Any ideas what is going on?

Unfortunately that completely out of the control of Roku. It's one of two things, either the channel/app isn't connecting correctly to the authentication server (so it's an app problem) or the server that provides the authentication (either the cable/satellite company or again whomever is responsible for the app) is acting up. If it's multiple apps that all authenticate against your cable/satellite account, it's probably a server issue. Your first place to complain is whomever created the apps that can't log in, such as ESPN. Roku themselves develops and maintains almost none of the apps available on a Roku device. 

The only other possibility that comes to mind is account credentials sharing. More and more are cracking down on credentials being used across locations. If that's not it, Dan's suggestions are the most likely cause.

I'll just comment Roku has allowed authentication to be a HUGE hassle every time accessing content.  Roku really needs a standard (monthly) authorization that works across all Roku apps and subscription TV services.   I'm not saying it easy to do but an authentication standard for the platform would make for a very enjoyable service.  

Seriously it is such a pain to always re-authenticate that is just easier to Chromecast as need to use a PC to consonantly authenticate with the Roku.  

Thanks for the notes here. 

As @atc98092 mentioned, each channel specifies the term length for their authentication systems inside their channel on the Roku platform. 

However, if you are running into an issue such as described with ESPN requiring daily re-authentication, I would recommend:

1.  Removing the channel from the Roku home screen by navigating to the channel tile, pressing the * key, and choosing 'Remove channel'.
2. Then, restart your Roku device from Settings>System>System restart. 
3. Once your device restarts, add the channel back once more from 'Streaming channels' on the home screen. 

If you are still encountering an issue with channel authentication from there, you'll want to follow up directly with the channel provider to report the issue you're encountering and request additional assistance. There are a number of other factors specific to each channel that could potentially cause the type of behavior you're describing which would need to be investigated by the channel provider themselves. 

Please feel free to PM me if you need any additional help and I'll see what I can do to assist you. 


Cheers,
Tanner

Thanks Tanner.   Issue I'm having is the different boxes are needing their channels activated at different times.  For example, my TCL tv is fine on the SCIgo channel but upstairs in my bedroom, the premiere is asking for activation. The 3500 I have in the family room apparently has an even different schedule.
Is this normal?  I have to carry my laptop around to chase these activation requests and it's annoying.

Would resetting as you described above on each box help?

I would recommend contacting any channel provider directly for more guidance about how their specific channel works. Different channels may have differing functionality. Often, each device is authenticated separately for each service. This is at the discretion of the channel provider. 


Thanks,
Tanner