Installation of System Center Configuration Manager CB and LTSB fails on Windows Server 2008

When the System Center Configuration Manager site server is running Windows Server 2008, installations, or upgrades of Configuration Manager current branch (versions 1511 – 1610) and long term servicing branch (version 1606) will fail to download and verify two required dependencies, resulting in overall setup failure.

The following errors are logged the setup.log file when the problem occurs:

01-09-2017 13:21:28.382    Configuration Manager Setup    8040 (0x1f68)    INFO: Downloading http://go.microsoft.com/fwlink/?LinkId=617193 as SQLSysClrTypes.msi

01-09-2017 13:21:28.557    Configuration Manager Setup    8040 (0x1f68)    INFO: WinHttpQueryHeaders() in Download() returned OK (200)

01-09-2017 13:21:28.964    Configuration Manager Setup    8040 (0x1f68)    INFO: Verifying hash for file 'D:\1606Updates\SQLSysClrTypes.msi'

01-09-2017 13:21:29.087    Configuration Manager Setup    8040 (0x1f68)    INFO: Verifying signature for file 'D:\1606Updates\SQLSysClrTypes.msi'

01-09-2017 13:21:29.113    Configuration Manager Setup    8040 (0x1f68)    ERROR: Failed to verify 'D:\1606Updates\SQLSysClrTypes.msi' authenticode signature.

01-09-2017 13:21:29.114    Configuration Manager Setup    8040 (0x1f68)    ERROR: File signature check failed for D:\1606Updates\SQLSysClrTypes.msi

01-09-2017 13:21:29.116    Configuration Manager Setup    8040 (0x1f68)    INFO: Downloaded file 'D:\1606Updates\SQLSysClrTypes.msi' is not valid

01-09-2017 13:21:29.117    Configuration Manager Setup    8040 (0x1f68)    ERROR: Failed to download required file

…

01-09-2017 13:21:58.951    Configuration Manager Setup    7384 (0x1cd8)    INFO: File sqlncli.msi already exists

01-09-2017 13:21:58.952    Configuration Manager Setup    7384 (0x1cd8)    INFO: Verifying hash for file 'D:\1ConfigMgrVnext\BaselineVersions\SetupDL1606\SharedManagementObjects.msi'

01-09-2017 13:21:59.136    Configuration Manager Setup    7384 (0x1cd8)    INFO: Verifying signature for file 'D:\1ConfigMgrVnext\BaselineVersions\SetupDL1606\SharedManagementObjects.msi'

01-09-2017 13:21:59.155    Configuration Manager Setup    7384 (0x1cd8)    ERROR: Failed to verify 'D:\1ConfigMgrVnext\BaselineVersions\SetupDL1606\SharedManagementObjects.msi' authenticode signature.

01-09-2017 13:21:59.156    Configuration Manager Setup    7384 (0x1cd8)    ERROR: File signature check failed for D:\1ConfigMgrVnext\BaselineVersions\SetupDL1606\SharedManagementObjects.msi

01-09-2017 13:21:59.157    Configuration Manager Setup    7384 (0x1cd8)    INFO: Verifying hash for file 'D:\1ConfigMgrVnext\BaselineVersions\SetupDL1606\ConfigMgr.AutoUpgradeScripts.cab'

01-09-2017 13:21:59.159    Configuration Manager Setup    7384 (0x1cd8)    INFO: Verifying signature for file 'D:\1ConfigMgrVnext\BaselineVersions\SetupDL1606\ConfigMgr.AutoUpgradeScripts.cab'

01-09-2017 13:21:59.167    Configuration Manager Setup    7384 (0x1cd8)    INFO: File ConfigMgr.AutoUpgradeScripts.cab already exists

01-09-2017 13:21:59.168    Configuration Manager Setup    7384 (0x1cd8)    ERROR: Verification failed: File D:\1ConfigMgrVnext\BaselineVersions\SetupDL1606\SQLSysClrTypes.msi not found

This occurs because these SQL Server redistributable files (SQLSysClrTypes.msi and SharedManagementObjects.msi) have been signed with the SHA-256 digest algorithm. Windows Server 2008 does not support SHA-2 signing which causes verification failure.