Possible to upgrade directly from V3.2.1 to latest?

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I have an RPI3 equipped with an old version of pi-hole (V3.2.1) that I would like to upgrade to the latest version. The RPI3 is running Raspbian GNU/Linux 9 (stretch) and pi-hole's DHCP service replaces the router's (disabled) DHCP service.

Can I update directly using pihole -up or is it, and/or the OS version, too old?

If not possible then is the only recourse a complete replacement of the OS and a fresh installation of pi-hole?

Lastly, I think I know the answer to this one but just to confirm, is pi-hole's DHCP server simply stretch's DHCP server? In other words, even if the latest version of pi-hole can be installed on stretch, the version of DHCP will still be stretch's version?

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Pi-hole is probably incompatible with Debian Stretch.

The support was dropped more than one year ago: Upcoming Pi-hole changes – Pi-hole and Bye Bye Debian Stretch :: Looking for testers

Also, the there are 5 and a half years between v3.2.1 (Dec 22, 2017) and the current v5.17.1 version (May 30, 2023).

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OK thanks. I figured it was unreasonable to assume that I could jump versions so far and with an outdated OS, but I needed confirmation.

Looks like I have a bit of work to do.

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The RaspberryPi Foundation discourages in-place release ugrades anyway.

Even assuming that you would be able to upgrade from Stretch to Buster, and then from Buster to Bullseye (and maybe from Bullseye to Bookworm) - that'd be likely far more time consuming than flashing the most recent RPi OS, installing Pi-hole and importing a Teleporter backup.

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Actually, my goal was to simply upgrade pi-hole, not the OS.

I'm aware of the requirement to replace major OS versions (not upgrade in place). That's why I was hoping it wouldn't be required.

In this case, starting from scratch won't be all that fast due to the need for re-installing (and re-configuring) other things that also run on the same RPi (NUT, CUPS, log2RAM, etc).

Anyway, it's something that eventually needed to be done and now it's overdue.

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UPDATE

Fresh installation and now running the latest of everything.

Operating System: Raspbian GNU/Linux 11 (bullseye)
          Kernel: Linux 6.1.21-v7+

Pi-hole version is v5.17.1 (Latest: v5.17.1)
AdminLTE version is v5.20.1 (Latest: v5.20.1)
FTL version is v5.23 (Latest: v5.23)

FWIW, I carried over the following file from the old host:
/etc/dnsmasq.d/04-pihole-static-dhcp.conf

All running smoothly so far. Now I have some reading to do to learn about the many new features (since 2018).

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