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For upgrading our Sitecore instance from 8.2 to 9, we want to use the Sitecore Update Installation Wizard, as mentioned on https://dev.sitecore.net/Downloads/Sitecore_Experience_Platform/90/Sitecore_Experience_Platform_90_Initial_Release.aspx
under the header "Upgrade options". However, I am wondering how this is supposed to work in a multiple machines environment. We have 1 CM server and 2 CD machines. And when we run the upgrade wizard on the CM machine, how will the assemblies and other files be deployed to the CD machines? How does it works?

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How to do upgrade multiple instances is described into upgrade guide Chapter 8:

The upgrade procedure for multiple instances depends on your environment architecture.

For a scaled environment, you must repeat the steps in this guide for each instance, with the exception of actions related to the database, which you must follow only once for each database .

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You can use the sitecore migration tools, from the sitecore website.

https://dev.sitecore.net/Downloads/Express_Migration_Tool/31/Express_Migration_Tool_31.aspx

Express Migration Tool 3.1 can help you migration to major releases of Sitecore 6.6,7.2, 7.5 or 8.0 to the latest version of Sitecore Experience Platform 9.0.

P.S. DMS data to xDB will still require the use of the conversion tools found on the Sitecore Experience Platform download pages

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