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According to this the site process is risky: https://support.stripe.com/questions/upgrade-openssl-to-support-tls-1-2

10.04 LTS (Lucid), you will need to upgrade to at least Ubuntu 12.04 (Precise). We recommend rebuilding your server, as the upgrade process is risky

Is that really the case or are they being over cautious?

d786b09987n
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    I don't know how risky the upgrade process from 10.04 to 12.04 is, but it seems risky to run either 10.04 or 12.04 as both have been EOL for years. 12.04 is (as the date code 12.04 indicates) from the year 2012. You ought to look at upgrading to 20.04, instead. – Håkan Lindqvist Apr 25 '20 at 16:36
  • for 20.04 it would probablty mean a reinstall, else upgrading through all the intermediate LTS versions. – Jasen Apr 26 '20 at 21:58

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Stripe is a payment processor who likely realized that the only way to get their customers on a modern TLS implementation is to make it extremely obvious they need to upgrade. TLS 1.2 is not the only criteria for a good software platform, it also needs to continue to get security updates and support. For Ubuntu, 14.04 or older is overdue for an upgrade.

As administrator, it is your job to accomplish such an upgrade. Test upgrades versus rebuilds in your environments. Customize an upgrade project to fit your needs.

Try it yourself. Read documentation on upgrading the OS. Upgrade the test servers. Try your applications.

General purpose OS distributions have experienced quite a bit of change in the past 10 years. Including Linux based, who constantly seem to be replacing components. In theory there is an upgrade path to keep the same OS instance, but in reality there will be tricky steps. Perhaps multiple tricky steps, due to the upgrade tools and software dependencies. Some paths may not be supported at all.

So if a new install is easier in the end, why not make one big leap and be up to date for a while? Ubuntu 20.04 is just out, new versions of things and several years of security updates.

John Mahowald
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  • I totally agree that upgrade should be done to the up to date version. For OP, there are some threads mentioning that since your version is not supported at the moment you will have to do a clean install. https://askubuntu.com/questions/1118584/upgrading-from-ubuntu-10-04-no-upgrades-available – Stuka Apr 25 '20 at 21:28