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Our organizations site is running Wordpress 4.9.18 and we are running with CiviCRM 5.20.0. Can I upgrade from CiviCRM 5.20.0 directly to the latest 5.41.2 or do I need to upgrade to one or more interim versions to get to 5.41.2?

If I need interim upgrades, what would those versions be and do I need to upgrade Wordpress along the way?

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I think you should be able to do it in one go, but you should definitely clone the server and do a test upgrade first particularly with that many versions (and of course back everything up first before doing the upgrade of the live site). I don't think you need to upgrade WordPress, but personally I would do this to the latest version immediately before or after.

Something I would check is the version of MySQL as I got caught out by that and version 5.7.5 is recommended. Version 5.6 needed setting changes that I couldn't make on my shareed hosting service, but 5.7 had the necessary settings by default.

Worth a look at the installation requirements at https://docs.civicrm.org/installation/en/latest/general/requirements/

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Our advice would be to try a full upgrade on a test/staging site first. This is the only way you'll be sure. Remember you'll need to upgrade extensions too as thats approx 21 months of upgrade being applied.

If a full upgrade fails then you can try it in parts i.e. going to 5.30.x first then up to the latest etc.

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