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I've been experiencing a problem where my always-on task stop working after a few days. This has happened 3 times in total now, two times when i click to see the logs it comes up totally blank, and once the output log's latest log can be seen to be from a about half-a-day back. I had to restart the task myself to get it working again. The task has worked for me a period of time before this issue started happening recently. Is there an issue on the server side?

There are no issues that we are aware of on our always on servers. If your task has just stopped, you can see if the process is running using the "Fetch process list" button on the Tasks page. If it is, then your task may just be stuck in a loop or waiting for something. It may also be affected by being slowed down because you'd used your daily CPU time.