[German]Administrators (or users) who have installed the October 2020 updates (for Windows 10 and Windows Server pendants) are probably facing issues. ConfigMgr and other tools will (possibly) not be able to download files for Microsoft Office 365 updates afterwards. The reason is a certificate error already described here in the blog, and confirmed by Microsoft. Here is some information about it.
In the blog post Windows 10 forgets certificates during upgrade I already pointed out that several Windows 10 versions forget their certificates during an upgrade. Workaround was to either import these certificates or uninstall the October 2020 update before upgrading Windows 10 to a new version. But the problem lies deeper, because it also affects the ability of Microsoft Office 365 to download patches (at least in SCCM ConfigMgr).
Office 365 suddenly brings download errors
German blog reader CL has pointed out this issue in this comment to the German edition of my article Windows 10 forgets certificates during upgrade (thanks for that). After installing the Windows 10 October 2020 update the download of updates for Microsoft Office 365 fails in (at least in the Office 365 installer of ConfigMgr). People get an error dialog, but without error details.
The above screenshot of the error message 'Download of Office 365 file failed, error =' is taken from the blog post 'Download of Office 365 file failed, error =, where someone describes this error for the Office 365 installer which can be displayed in the Configuration Manager. In his blog post, he works through various error causes (firewall configuration), which are not relevant here.
October 2020 Updates delete Certificates
In the blog post Windows 10 forgets certificates during upgrade it was pointed out that several Windows 10 versions forget their certificates during a feature upgrade. In the blog post 'Download of Office 365 file failed, error = ' the author writes that the cumulative update KB4577668 for Windows 10 version 1809 and Windows Server 1809 and Windows Server 2019 also causes this download issue due to deleted certificates. Microsoft does not announce issues within it's support article for the Oct. 2020 update.
But Microsoft employee David James (Director of Engineering ConfigMgr & Desktop Analytics) confirms the problem in the above tweet. The Windows October 2020 patches may prevent ConfigMgr and Memcm from downloading Microsoft Office 365 updates in both the Administrator Console (Admin UI) and ADR (Automatic Deployment Rules). James states the cumulative security updates for Windows 10 (also valid for Windows Server 2018/2019) from October 2020 as the cause. These updates causes a certificate loss.
Microsoft is now aware of the error and according to James, they are working on a hotfix and a support fee. James states that the only fix at the moment is to run the administrator console (Admin UI) of ConfigMgr on an unpatched Windows 10 system (but probably the corresponding server counterpart). He hopes that the hotfix will only be installed on the server side and not become a patch for the Windows 10 clients as well.
But I recommend affected administrators to have a look at the certificate import solution mentioned in my blog post Windows 10 forgets certificates during upgrade. JoyQiao-MSFT from Microsoft has suggested and briefly outlined this in this Microsoft Q&A forum thread. Maybe it helps those affected (I myself can't test anything due to lack of a suitable constellation).
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