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We are finding recently, with our wsp deployments, that on some of the WFE/APP servers in our farm that the assembly contained in the WSP, which should be gaced, is updating some servers but not all. Almost like the assembly in the GAC is locked on some servers but not others.

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I have run into this before using WSP Builder and the only thing I could get to work was to run STSADM and go through a full uninstall, including removing from the solution store.

Are you running STSADM -o execadmsvcjobs after upgrading as well?

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Have a look at the SharePoint trace logs on each machine for messages related to those DLLs.

What does the Solution Management screen say about deployment to these servers?

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Solution Management screen indicates all good, no problems. I'll look at the logs. – Brian Jul 8 '10 at 6:34
Good question, I upvoted it. – Muhimbi Jul 8 '10 at 9:41

Are you fully retracting and removing your originally deployed solutions before updates?

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Utlimately that's the point we get to, but we try to run an upgrade solution first. I've seen this on upgrade and full retraction/redeployment. – Brian Jul 13 '10 at 1:24

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