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Windows Sever 2019 not optimizing drives weekly even though it says it's set up to do so

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I have a Server 2019 installation that is just not trimming the drives even though it says it is set to do so each week.

On the defrag (Optimise drives) app it shows "Current status: Needs optimisation (N days since last run)" while also saying "Scheduled optimisation: On [...] Frequency: Weekly".

I have to click Optimise myself whenever I remember that it's not doing it.

Anyone know how I could debug/fix this?

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