Is the contractor who wrote your system retiring? Don't ask them for documentation. Have whoever takes over build, release and restore the system with them before their last day. The questions that come up are what no document captures.

Restoring the database is not the whole SQL Server upgrade. Agent jobs, SSIS packages, Reporting Services reports, linked servers and logins sit outside it and do not come across on restore. List them first.

.NET Framework 4.6.2 stops getting security fixes on 12 January 2027. Versions 4.7 to 4.8.1 remain supported for as long as the Windows version they run on. Worth knowing which one your older apps target.

Paying for bespoke software does not make you its owner. In the UK, copyright stays with the supplier unless a written, signed agreement assigns it to you. Worth checking before you need to change supplier.

An older business system rarely costs more because of its code. The cost rises around it: support fees, old licences, oversized servers, staff time on workarounds. List every cost against the part of the system it pays for. Some may pay for things nobody uses.

Umbraco 13 stops getting security fixes on 14 December 2026. If your website or portal runs on it, plan the move to Umbraco 17 now rather than in the last fortnight before Christmas.

Today, 13 October 2026, Office and Access 2021 reach end of support. Paid Extended Security Updates for Windows Server 2012 and 2012 R2 end today too, and Windows Server 2022 leaves mainstream support.

Slow business software is rarely fixed for long by a bigger server. A query scanning a growing table keeps getting slower. Measure where the time goes first: the database usually shows a few queries cause most of the waiting.

"The search should be fast" is not an acceptance criterion. Nobody can say whether it passed. "Results appear within two seconds for 50,000 customers" is one. Agree them before the build, not at delivery.

Windows Server 2016 stops getting free security updates on 12 January 2027. Before planning the upgrade, list everything else that runs on that server: scheduled jobs, file shares, links to other systems.