Piwheels currently has certificate issues, updates might fail due to this

piwheels, the additional python package index configured in Raspberry Pi OS and thus also OctoPi, is currently experiencing an expired SSL certificate on one of its download endpoints. This can cause OctoPrint updates to fail. The problem has been reported to piwheels and will hopefully get resolved soon. In the meantime best refrain from performing updates.

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This has been resolved on piwheels' end.