bin/ExSMIME.dll Copy Error During Exchange Patching

I have seen a lot of this, and there are some documents online but none that described what I was seeing. I was getting the following on an upgrade of Exchange 2013 CU10 to CU22 (yes, a big difference in versions):

     The following error was generated when “$error.Clear();
           $dllFile = join-path $RoleInstallPath “bin\ExSMIME.dll”;
           $regsvr = join-path (join-path $env:SystemRoot system32) regsvr32.exe;
          start-SetupProcess -Name:”$regsvr” -Args:”/s `”$dllFile`”” -Timeout:120000;
         ” was run: “Microsoft.Exchange.Configuration.Tasks.TaskException: Process execution failed with exit code 3.
    at Microsoft.Exchange.Management.Tasks.RunProcessBase.InternalProcessRecord()
   at Microsoft.Exchange.Configuration.Tasks.Task.<ProcessRecord>b__b()
    at Microsoft.Exchange.Configuration.Tasks.Task.InvokeRetryableFunc(String funcName, Action func, Boolean terminatePipelineIfFailed)”.

The Exchange Server setup operation didn’t complete. More details can be found
in ExchangeSetup.log located in the <SystemDrive>:\ExchangeSetupLogs folder.

In this error the file ExSMIME.dll fails to copy. You can find the correct copy of this file in the CU source files at …\CU22\setup\serverroles\common. I copy the ExSMIME.dll file from here directly into the \Program Files\Microsoft\Exchange Server\v15\bin folder and then restart the upgrade.

I have found that the upgrade fails again here if it things there is a pending reboot due to other installations and I have also seen at this point the detection for the VC++ runtime fails. I have documented this elsewhere, and the workaround for the is found at

A reboot later and the installation is successful. The error somehow seems to think that the file is not where it is looking for it. In the ExchangeSetup.log file it records the issue as “Error 3”, which generally means “not found”!

Leave a comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.