RasPi Imager V2.0 + HA + Migration from microSD to SSD Problems / Loop

Installation
1

I need help.

:bulb:in case it’s relevant, please note that it is January 2026.

Using Raspberry Pi 5, always been fine with HA via 256GB microSD (ror about a year now). Attempting to migrate to SSD with Argon board/case and Inland (Microcenter brand, reputable) SSD stick.

I’m flashing to SSD from MacBook Pro using latest v2.0 Raspberry Pi imager (which has no advanced options and was dropped in late 2025…this ALREADY has me a little spooked as the potential culprit). Using a Sabrent USB NVMe enclosure.

I boot via SSD, it’s very fast, CLI looks normasl on my TV (mini HDMI from the pi → TV) and, on my Mac, at :8123, I’m stuck on a loop for days after a random sea of logged junk:

{datetime from 10 months ago} INFO (MainThread) [supervisor.updater] No Supervisor connectivity, delaying version fetch
{datetime from 10 months ago} WARNING (MainThread) [supervisor.homeassistant.core] Error on Home Assistant installation. Retrying in 30sec

It loops those forever. No, it’s not a “wait longer” thing.

I’m plugged in via Ethernet, my Eero network sees the Pi, it hands me a different IP than I had on the microSD, naturally, I can see the UI/log on my Mac via :8123, and I have the CLI up on a TV. I can provide full log if it helps, but note that this is happening on January 14, 2026 and the date in my logs is sometime last June for some reason. I don’t know if there is some date mismatch that is breaking some cert - or, if that is the case, if it’s just a thing that is gonna happen until updates deploy since we’re now in 2026 and the system may very well be saying “WHOA, HOLD UP, IT’S NOT THE FUTURE, SOMETHING IS UP.”

I have been at this for a full day and I really need a hand, alternatives, any wisdom, and maybe a shot of tequila.

2

This triggers some memories of hardware incompatabilities with some SSDs.

Your MAC should not have changed, regardless of what operating system is loaded. You may wish to configure a static IP address reservation on your router in the DHCP section.

From numerous reports on installations hanging, my guess, supported by a lot of observations, is NTP Time or mDNS has not updated at that point in the installation cycle, and this is interfering with installation software and certificate dates being invalid. This may be a faulty sequencing issue with the installation software, or a certificate issue, or a dependency on a network connection too early in the process.

I suspect this is a faulty CORE bundle dependancy that everybody downloads using the Raspberry Pi imager, but I am not in a position to carefully debug this issue.

I have also observed that rebooting and re-trying seems to sometimes pick up the current time, and then you get a network connection, and it seems to continue to successful completion.

Preserve the logs, report it on GitHub as a CORE INSTALLATION PROBLEM, and retry booting after you have allocated a static IP Address on your router.

Others will comment, I’m sure.