Group Policy installation failed error 1274

I'm trying to deploy an MSI via the Group Policy in Active Directory. But these are the errors I'm getting in the System event log after logging in:

• The assignment of application XStandard from policy install failed. The error was : %%1274
• The removal of the assignment of application XStandard from policy install failed. The error was : %%2
• Failed to apply changes to software installation settings. The installation of software deployed through Group Policy for this user has been delayed until the next logon because the changes must be applied before the user logon. The error was : %%1274
• The Group Policy Client Side Extension Software Installation was unable to apply one or more settings because the changes must be processed before system startup or user logon. The system will wait for Group Policy processing to finish completely before the next startup or logon for this user, and this may result in slow startup and boot performance.

When I reboot and log in again I simply get the same messages about needing to perform the update before the next logon. I'm on a Windows Vista 32-bit laptop. I'm rather new to deploying via group policy so what other information would be helpful in determining the issue? I tried a different MSI with the same results. I'm able to install the MSI using the command line and msiexec when logged into the computer, so I know the MSI is working ok at least.

You're seeing the dreaded scourge of asynchronous policy processing. It's not a "feature" (and was default-off in Windows 2000 but default-on in Windows XP and above) and causes exactly what you're seeing-- non-deterministic behaviour with processing some types of GPO settings.

In a GPO that applies to that computer, add the following setting:

• Computer Settings
  • Administrative Templates
    • System
      • Logon
        • Always wait for the network at computer startup and logon - Enabled

After you set that (and allow the GPO to replicate if you're in a multi-DC environment), do a "gpupdate /force /boot" on the subject PC. It will reboot and you should see the software installation occur.

The "Always wait for the network at computer startup and logon" slightly slows down the startup and logon because all GPO extensions are allowed to process, but the upside is that all GPO extensions are allowed to process.

I tried the Always wait for the network at computer startup and logon - Enabled setting from the answer by @Evan Anderson, but it wasn't until I added this setting below as well that allowed the software to install. Not sure if it was a combination of both settings or not. It's working now, so I'm leaving both settings.

In a Group Policy applied to these workstations, navigate to:

Computer Configuration > Policies > Administrative Templates > System > Group Policy

Enable the Specify startup policy processing wait time. Set Amount of time to wait (in seconds): = 120

120 might be overkill, but that worked for me. Other forums suggested setting that to 30 seconds. Even though 30 seconds default (when policy is not set), forcing it to 30 seconds worked for them.