If we try to manually install the IIS URL Rewrite Module bundled in RTM version we get this: The issue is that Windows Server 2016/2019 has IIS 10 and the IIS URL Rewrite Module included in the Skype for Business Server 2015 RTM won’t detect this IIS version. Prerequisite installation failed: RewriteModule – End Error Message from rewrite_2.0_rtw_圆4.msi -– Property(S): OriginalDatabase = C:\ProgramData\Microsoft\Skype for Business Server\Deployment\cache\.0\rewrite_2.0_rtw_圆4.msi Property(S): DATABASE = C:\Windows\Installer\2ea25a.msi Property(S): MsiWin32AssemblySupport = 3.0 – Error Message from rewrite_2.0_rtw_圆4.msi. Installing rewrite_2.0_rtw_圆4.msi( REBOOT=ReallySuppress )…failure code 1603 While deploying a new Skype for Business Server 2015 Pool in the lab we got the following error message in the Deployment Wizard Step 2 (bootstrap):
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