Apple Watch issues again

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21

A different wireless network on your own setup? Is this additional Wifi setup to use Pihole? If it is, can you temporarily change that Wifi configuration to use another DNS besides Pihole (like 9.9.9.9 or 1.1.1.1), then renew the watch/phone DHCP lease?

We really need to know whether or not Pihole is a factor in this issue in order to provide useful help. The way to do that is test with Pihole involved (which you've already done) and test with Pihole completely bypassed.

As for whether DNS cache is impacting the issue, changing DNS servers on the client as previously suggested would remove the possibility that DNS cache is the cause.

22

I have a strange setup where I have a raspberry pi running Network Manager with Ethernet set to shared

So I can connect to the main router with no pihole or connect to my access point after the raspberry pi that uses pihole

There two completely different subnets

23

I got a new iPhone and since then have not had this issue

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Takes it about 20-30 seconds but it does work 99% of the time now

It must have not liked my old iPhone 11

25

so the solution was to upgrade my phone, no idea why it worked but I also ended up factory resetting my apple watch in the process of setting up my new iPhone so that might have helped

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