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Can't relate with that... I'm still hosting some WordPress websites for clients from a few years ago. I'm afraid to upgrade PHP versions because many things broke in the past. True, it's not the WordPress core but the plugins that usually break, but I can't think of a single client of mine that doesn't have at least 3 plugins installed.

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Ditto. I just did a project upgrading hosted websites to the latest PHP from PHP 5.6. These are already sites that vetted past the obvious issues of the mysql and mcrypt APIs going away, and these sites were all maintained in at least the last 4 years (I host sites that haven't been touched for over a decade, they aren't getting upgrades).

Even with these "cherry picked sites", we had about a 30% failure rate dealing with the new PHP. Ranging from total non-function of some random CMS, to mostly errors printing all over every page due to some deprecated or change of code behavior in the site templates.

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