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I inherited a badly out-of-date Drupal 6 multi-site instance. There is only the production instance. (yeah, that gives me a warm-fuzzy!)

Many modules are several versions behind and the core is several versions behind.

Does the order in which I perform the updates matter? I'm thinking update core first, then update the modules, but I'm just not sure.

Anyone care to advise?

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Order does matter.

Sadly, it's hard to tell exactly how it will matter in your situation. If you can, make a dev copy of this site and experiment on it. I would either go with core-first or with all at once. But that's my intuition, and actual tests on a copy of actual site matters much more.

Usually it's OK to jump all versions in-between the one you have and most recent one. For modules, sometimes, rarely, it's good to use most-recent minor version and don't install next major version at all (if both are maintained), or install most-recent minor and then update major. Sadly, it's different for each module, so fastest thing would be to update everything straight to the recent version, and see if / what broke. Of course, this is only feasible on a dev copy, not production.

  • Thanks - that is what I was thinking too. A follow-on related question would be if I should apply the most-recent CORE update (even though there are about 9 versions in-between) or should I apply each core update separately until it's completely up to date? – MzEllie Sep 25 '15 at 20:25
  • @MzEllie feel free to edit this into your question, and I'll add this part to my answer. – Mołot Sep 25 '15 at 21:07

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