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After building a WSUS server in a windows 2016 server I get failed to synchronize error followed by 'System.Net.WebException: The underlying conne...'

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So I started with the basic procedure of adding the Windows Sever Update Services (WSUS) roles.

After doing so I created a self-signed certificate and add the domain names where required.

Image of left pane that contains the create the cert actions

Creating a self signed cert image

Then I would configure the HTTP and HTTPS ports respectively and bind the WSUS to my SSL certificate

Image of Binding WSUS to the certificate

Next, I enforced encryption on WSUS directories under the WSUS administration sites which are 'APIremoting, ClientWebService, DssAuthWebService, ServerSyncWebService, SimpleAuthWebService' by checking the 'Require SSL' check box.

Image of encryption enforcement

After that, I would navigate to 'C:\Program files\Update Services\Tools' folder and write the command that would tell the WSUS to use SSL

Powershell command

However now when try to sync it throws an error.

Update services window showing the error and failure to sync

Score:0
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I think this is a hardware problem how much free space do you have? if that doesnt solve it try to stop and start certificate certificates manualy

yatso1 avatar
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I already tried stopping and starting those manually, i also tried to increase the maximum memory limit
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