Licensing & payments · Extending your trial and free offers
Why can't I extend my trial a second time?
Short answer: Extensions are allowed once per Mac and once per email, and only when one is on offer, so the option disappears after you've used it.
Trial extensions are limited — often to just one — and counted per Mac and per email address together, so once you've used them the option no longer appears. It also only shows when an extension is currently being offered.
If you need longer to decide, you can still pick a plan, apply a coupon, or activate a code you've been given — all from the same trial-ended screen.