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Beginners • How should I properly setup my Raspberry Pi 5 headless?

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Since this article would have many questions, I'll 'contain' my questions inside of quotes.

I recently bought Raspberry Pi 5 and tried to use Raspberry Pi OS Lite, because it would contain many useful tools for configuring RPi.

My ultimate goal is to run many 'services' as Docker image running on headless Raspberry Pi 5.

My attempts are splitted with two different environments. One is 'Connected to internet via Wi-Fi' and the other one is 'Connected to internet via LAN'.

Case 01: Internet via Wi-Fi

I first tried using Raspberry Pi Imager and choose Raspberry Pi OS Lite x64. After filling all optional details about keyboard, region, account etc., including Wi-Fi AP information, I flashed the OS to DRAM-less NVMe SSD. After that, I connected the SSD to RPi, and booted it.

At that time, I didn't have any Micro HDMI cable or monitor, so I just had to pray for RPi has correctly configured and open SSH port automatically.

But I soon encountered a critical problem: SSH 'lags'. The screen doesn't get 'updated' (show new character typed) when I type words in SSH session. But after approx. 10 seconds, everything I've typed are suddenly appears, along with command execution result. This kind of problem happened quite often.

The CPU temperature was less than 50 C, so I don't think it wasn't throttling.
Why the problem (nothing is updated but everything suddenly updated at once) happened? Is it because of Wi-Fi?
Case 02: Internet via LAN

In this time, I've got Micro HDMI cable and LAN cable to connect to router, which my PC is also connected. So, RPi and my PC would be in same network.

Rather than relying on Raspberry Pi Imager, which requires me to detach DRAM-less NVMe SSD from RPi by dismantling RPi from its casing, I've decided to try PINN.

Since PINN offers me options for downloading OS image from internet, if connected to, it will free me from disassembling RPi and HAT, Casing etc. whenever I need to re-install the OS. It also provides OS backup feature, which is very awesome things to have.

But PINN does not provide any option for pre-config OS like setting Wi-Fi profile, enabling SSH service etc. So I connected Micro HDMI cable and USB Keyboard to it.

After successful initial boot, I've updated everything via APT. At the last time of upgrading the packages, a weird error spammed the console.
I don't remember much about the error, but I remember this: APT tried to delay something, but failed.
Is it safe to ignore such error?
I've also found weird problem.

Everything works fine when Micro HDMI cable is connected. I can connect RPi via SSH, too.

But when I disconnect Micro HDMI cable and reboot, I can't connect to it. My router sees RPi, but I can't connect to it. Internal IP address, '.local' address, nothing works.
Why RPi didn't properly boot when no monitor is detected?
I've found some article saying that putting 'hdmi_' stuff in 'config.txt', but I believe those are outdated guide, which won't work on RPi 5.

After that, I gave up using PINN and re-tried Raspberry Pi Imager once more. Just like how I did in first trial, I've filled everything. So, in normal state, it should be configure everything (and) SSH, then open port 22. But it didn't. Since it was connected to HDMI cable, I could see TUI for setting keyboard layout, and creating new account. But those things are already configured by Raspberry Pi Imager.
Does 'auto-configuration' only happens if no monitor is detected?
I've encountered so many problems that would require re-installing the OS, and this really make me exhausted...

Statistics: Posted by tetratheta — Tue Feb 24, 2026 5:40 pm — Replies 2 — Views 73



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