The second reboot is weird, it looks like it’s going back in time.
But it also sounds like the boot loader tools are not working correctly on the second partition. Can you add a state script, ArtifactReboot_Enter_00_Debug and ArtifactReboot_Leave_00_Debug where you execute grub-mender-grubenv-print, so that we can see what the environment is before and after the reboot?
Apart from that debugging, here are a few other things to try:
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In general using an old server with a new client is not supported, only the opposite is (new server and old client). Try upgrading the server to the latest version.
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Can you try installing a file update before you install a full rootfs-image update? Just install a dummy file in
/tmpfor example.