Hi @sarahwiechers

If you run ls -l /opt/digitalocean/bin/do-agent it will tell you the install/update date.
If the automatic update works, then the date should be about 5 days ago, since that was the latest release.

I think you might be experiencing something similar to this:
https://github.com/digitalocean/do-agent/issues/21
What happens if you run the installation script again?

I've been seeing this as well. I wouldn't worry too much about the error itself beside it being slightly annoying.
I opened a support request to inform them - DO are aware of the issue and are working on it.

The last update date is the 19th, which seems to be fine. Running the install script again results in
"do-agent is already the newest version (0.5.0).
0 upgraded, 0 newly installed, 0 to remove and 5 not upgraded."
Seems to be fine as well.
It is still good to know someone is working on this, since it is quite annoying. So, thanks for your help!

Be seeing the same message in the last two days as well for all my servers. Glad to hear DO is working on it.

Also seeing this message

Ditto, even after purge/reinstall via Debian repo.

Unable to update do-agent: Update: Error initializing repository: tuf: failed to decode root.json: expired at 2017-07-22 15:27:54 +0000 UTC

Same here. It seems I need to disable it. Annoying that the logchecker is nagging about it each hour.

Annoying that the logchecker is nagging about it each hour.

You can add something like

do-agent\[[0-9]+\]: [0-9/: ]{19} Unable to update do-agent: Update: Error initializing repository: tuf: failed to decode root.json.*

to a file in /etc/logcheck/ignore.d.server/ to filter these messages from the logchecker output.

Mine is borked too..

Even did full clean-up and re-install, nothing
Unable to update do-agent: Update: Error initializing repository: tuf: failed to decode root.json: expired at 2017-07-22 15:27:54 +0000 UTC

Have the exact same error, nothing I did helped.