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I need to update WordPress from version 4.4.9 to 4.7.4 also there are 17 plug-ins that need to be updated as well. My question is should I update the plug-ins first, and then proceed to update WordPress or vice versa? I'm using this link as a guide: https://codex.wordpress.org/Upgrading_WordPress_Extended#Upgrading_Across_Multiple_Versions

thanks!

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I think it depends on the plugins which way will be better. I had a similar situation with this many plugins, but i had to update WordPress just from 4.7 to 4.7.3. My update order was:

  1. WordPress
  2. Theme
  3. Plugins
  4. Translations

If you are not sure, i think the best way is to copy your WordPress to a private server (for example you can use XAMPP on your local computer) and test the update process in there. If all works, it should work on your real instance as well. Read this article for more information on copying your WordPress instance.

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