Update Third-Party Applications on VMs

[ager24]

Hi,

I am pretty new to vSphere. Please be kind to me when it's a stupid question. 

Can I update third-party Software on different VMs automatically?

For Example:

I have three VMs on each of them is a Web Application Installed. Now I need to install a newer version of that Web Application on each of them. I could make a Template and Override all VMs but then the User Data would be deleted.  

What would be the best way to achieve this? 

Regards, 

Aftab 

[continuum]

Use a second vmdk for user-data.  Then you can keep the second disk while using a newer version of the system disk.