How to run bulk WordPress updates without breaking client sites
Updating forty sites in one click sounds risky. With a fixed order, a health check and a rollback plan it is safer than updating by hand.
Sanne de Vries
Most agencies delay updates because a single broken checkout page costs more than a month of maintenance revenue. The answer is not to update less often, but to make every update boring and repeatable.
Start by grouping sites by risk. Brochure sites can be updated first, shops and membership sites last. Run the low-risk group in the morning, check the result, then let the rest follow.
Always take a database backup right before an update run and verify that the backup actually finished. A backup you never checked is not a backup.
After every site is updated, hit the front page and one deep page automatically. A 200 response with the expected page title catches ninety percent of failures within seconds.
Finally, log everything. When a client asks why a plugin version changed on a Tuesday, you want a timestamped answer, not a guess.