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In our farm we have several features that add extra themes. These features automatically update the spthemes.xml file in the template\layouts\LCID directory on activation (and remove the lines on deactivation) All the 'file updating magic' happens in the feature-activated event receiver.

Same for the pdficon in the docicon.xml file.

We just added a new WFE to the farm, but the changes aren't replicated to the files (docicon.xml and spthemes.xml) on the new server.

What is the best approach to keep these kind of files in sync when adding a new WFE?

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When you join a new WFE to the farm, all existing features that are deployed should be automatically deployed to the new WFE as part of SharePoint's process. Go in to "Manage Farm Solutions" and click on one of your feature WSP's to see if there's an event in the history showing that the feature was deployed to the new WFE. It sounds like you may have encountered issues during adding the new WFE to the farm; it could be the permissions on the farm mis-configured so the timer job can't be run correctly.

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Central Admin reports a succesfull deployment: [ServerName] : The solution was successfully deployed. Deploying doesn't mean it will run feature-activation-code, right? –  Dribbel Oct 19 '11 at 14:28
    
Correct, deployment will copy '_layouts' artifacts and such, but if you have say an event receiver that fires on activation, that does not re-run. If that's where your changes are taking place you should be able to just deactivate and reactivate to solve your problem. –  webdes03 Oct 19 '11 at 14:29
    
An off-on cycle it is then. Or there must be an other way to updated spthemes.xml (I rather would have had separate config files which SP would iterate over, to get its themes) –  Dribbel Oct 19 '11 at 14:55
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Is it a true feature that manages it all? Are there additional updates you may need to make to enable it? (i.e. copyappbincontent)

WFEs should automatically process and keep themselves updated against features. I think the timer service should be running on each WFE to ensure they're up to date.

Have you tried deactivating and reactivating the feature?

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'Have you tried turning it off and on again.' A classic :) I'll try that, but if I'm correct I shouldn't have to do that. –  Dribbel Oct 19 '11 at 14:30
    
I agree, you shouldn't have to, but a good test to ensure things are running properly. –  David Lozzi Oct 19 '11 at 17:13
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