Should i upgrade to stretch?

Does Pi-hole now support stretch?

Im running on dedicated Pi2, alongside OpenVpn.

Should I upgrade to Stretch lite?

A previous discussion lead me to not upgrade on older version of PiHole

The RPF doesn't suggest an in place upgrade for major releases, so your best option would be to save the settings of the Pi-hole, flash a new SDCard with Stretch lite on it and import your saved settings. But there are no issues on Stretch now that should cause you problems.

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hmm, that's interesting as I didn't come across this when I upgraded my Pi3 from Jessie Lite to Stretch Lite.
I guess it makes sense as the way you describe is cleaner.
Im thinking id need to back up more than the Pi-Hole native 'teleporter' does?
What in particular should I look out for.

The only reason im reluctant to do it this way is I had a lot of trouble when initially setting up Pi-hole...it wasn't blocking on Android devices being one issue, not blocking when connected to VPN another.

All of those niggles are now ironed out, but im concerned I may face similar problems?

I'm personally a fan of "if it's not broke, don't mess with it"? As in: do you specifically need a feature that Stretch has added?

Raspbian Jessie will enter LTS May 2018, after which point Raspbian will probably not continue to offer support: Support timeline for Jessie - Raspberry Pi Forums

However, as long as your device isn't offering public service (:flushed:), has no known or zero-day exploits on any service facing the LAN (:crossed_fingers:),and your LAN has no hostile actors looking for known or zero-day exploits (:crossed_fingers:) you ought to be fine just leaving well enough alone. If the first or last of those are true, you've got enough problems on your plate as it is.

Newer isn't always better...but in the case of Debian it usually is :wink:

I still have a Windows XP install or two that I protect from "the internet"...as long as no one can talk into or out of them, they're perfectly content purring along by themselves in peace...

Where does the line between 'roll your own processor' and 'blindly execute code that's traveled over dirty pipes' lie? :man_shrugging: Do you get any tangible benefit from the effort expended? :man_shrugging:

What an odd reply.... condescending almost :thinking:
I'm also of the "if it ain't broke don't fix it" philosophy. However, I was under the impression that with Stretch came various performance improvements and security enhancements?

My pihole is not open to the internet, nor offers any public service....why would it?
Zero-day exploits?
Hostile actors?
Let's just pretend we aren't all as intelligent as you and I'll say...."eh?"....given this means nothing to me, I'm gonna go ahead and assume they are bad, but I do not suffer (?) from / haven't fallen victim to such problems.

Agreed, newer doesn't always mean better, but in most cases with most things in life, in generally does.

Windows XP machines.... irrelevant.

Just my personal opinion regarding "should I upgrade to stretch", and I wanted to explain why my opinion is such that it is! Everyone's use case is different, and I can't even guess at yours :slight_smile: