Trying to upgrade but "homeassistant" commands in the CLI are stuck on "Processing..."

I’m looking into upgrading HA running on my Pi, although when I run some commands the CLI is just stuck on “processing”.

core-ssh:~# hassio homeassistant check
⢿ Processing...
core-ssh:~# hassio homeassistant update
⢿ Processing...

Here’s my info dump if it helps:

core-ssh:~# hassio homeassistant info
arch: armhf
audio_input: null
audio_output: null
boot: true
image: homeassistant/raspberrypi-homeassistant
ip_address: XXX.XXX.XXX.XXX
last_version: 0.110.4
machine: YYYY
port: XXXX
ssl: true
version: 0.102.3
version_latest: 0.110.4
wait_boot: 600
watchdog: true

Is there any way to debug this? All I really want to do is update HA