The Canyon ReviewThe deadlines your stack hits in the next twelve months, ranked by pain
EOLs, ESU cliffs and certificate deadlines between now and next August, in one table you can tape to the wall. Check it against your estate this week.
No ranking this week. A calendar, because the next twelve months are unusually dated, and every line below is the kind that costs triple when discovered late.
The table
| Date | What happens | Who feels it |
|---|---|---|
| Oct 13, 2026 | Windows 10 consumer ESU ends; enterprise ESU year two pricing doubles | any fleet still on 10 |
| Nov 2026 | .NET 8 LTS support ends (lifecycle) | services pinned to the 2023 LTS |
| Jan 12, 2027 | Windows Server 2016 extended support ends | the servers everyone forgot |
| Mar 2027 | TLS max certificate lifetime steps down again on the published slide from 398 to 47 days | anyone renewing by hand |
| ongoing | Postgres 13 is already out of support (versioning); 14 follows in Nov 2026 | that one RDS instance |
How to use it
One hour, this week: grep the estate for each row. Not the CMDB, the estate; the difference between those two lists is where the incidents live. For every hit, write one of three words next to it: upgrade, replace, or accept, with a name and a month. "Accept" is a legitimate answer when someone senior signs it; a blank is not.
The pattern across every row: none of these dates is a surprise. All of them were published years out, which means every one that becomes an emergency was a filing failure, not a technology event. The vendors did their part. The wall calendar does the rest.
Prices move, dates mostly don't. When one does, we will correct this page and say so. Tape it up.