It’s not a huge issue, but after SSHing into my DO server I am greeting by a message stating “x” amount of updates are able to be installed.

After running sudo apt-get update then sudo apt-get upgrade and logging out the message still persists.

Do I have to wait until the ~next~ day for it to disappear - or what makes the messages not occur?

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I have never run into this myself but I found this post that talks about the exact issue you’re encountering.

In short, this has been shown for some people to resolve the issue:

sudo aptitude update
sudo aptitude safe-upgrade