When VMware tools times out after 300 seconds you.......

Set it higher! 

I see this issue ALL THE TIME. The error messages looks like this:

Error - Timed out waiting for VMware Tools after 300 seconds

But why am I getting this, you might ask. Well 300 seconds is 5 minutes. The average boot time for a Windows VM is right around 3-4 minutes. This leaves just 60 seconds for VMware tools to come up and start talking to vCenter. Depending on how many other services are starting at the same time, this might not happen!

So what do we do to fix it?

We set it higher! Assuming that it really is just not starting up in time, we can set the wait for VMware tools time globally. To do this, follow these steps:

1) Open Site Recovery Manager in vCenter

2) In the "Sites" section, right click your local site and select "Advanced Settings..."

3) in the "recovery" section, scroll to the bottom and you will see recovery.powerOnTimeout

4) Set recovery.powerOnTimeout to whatever time value you want (I usually set it to 900 seconds)

5) Repeat these steps on the DR site

Now your SRM server will wait for 900 seconds for VMware tools to come up. If you set it for 900 seconds and it STILL isn't working, log into the server as soon as it boots up and see if VMware tools is starting. If it is, you have a different issue, if it's not, time it and find out how long it takes to start and set this setting accordingly. Last thing here, setting the timeout to 900 seconds does NOT mean that it will always wait 900 seconds. It simply means that is the longest it will wait. So for instance, let's say that VMware tools comes up in 302 seconds, you will only wait 302 seconds, not the full 900. In this manor, you may have a higher success rate and still only wait about 5 minutes. Hope this helps!