2

It appears Raspbian 9 can't automatically update to Raspbian 10.

Is the OS still getting security updates?

What advantages and disadvantages are there in staying on Raspbian 9?

When will it approach its EoL?

3

There's some level of support for Raspbian Stretch still, but it is not an LTS release. All new development is on Raspbian Buster, all support for RPi4 is exclusively on Buster.

What's preventing you from upgrading?

It is possible to do an upgrade from Stretch to Buster, although it is not recommended. Six of my 17 raspberries got upgraded that way.

There's no announced date when support ends.

1

Debian 9 (which is the basis of Raspbian Stretch) has an End of life date ~2020 so its continued use should be OK until mid 2020 (exact date unspecified).

See https://wiki.debian.org/DebianReleases

There is an unofficial LTS beyond this, but it is doubtful that the Foundation will be providing updates for Raspbian Stretch.

Raspbian Buster is preferred, but still has some outstanding issues, and a number of packages have not been ported to Buster.

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