SSH (publickey) error on Pihole

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MikeAqua

7773 posts

Uber Geek

#320277 25-Jul-2025 14:31

I have a new pihole set up and running as of last week. When I first wrote the image (Pi Lite 64bit), I cocked up the SSH key side of things. So I overwrote the image, this time stipulating password validation for SSH connection.

The installation and initiation all went well. Ads are being blocked, but ....

If I try and connect by SSH I get the following error message

Permission denied (publickey)

I went into the SSH config file and turned password connection on. I found and deleted some password keys on the pi. I deleted password keys on my PC.

I'm still getting the error. Does anyone have any suggestions?

Do I need to format the SD card and start again?

Edit: I'm trying to SSH from

C:\Users\[username]>

Mike

kyhwana2

2566 posts

Uber Geek

#3397073 25-Jul-2025 14:43

Did you restart the ssh service on the pi after you changed the sshd_config file?

MikeAqua

7773 posts

Uber Geek

#3397304 26-Jul-2025 16:05

I did. But maybe not after I deleted the SSH keys that I found. I'll try that.

Mike

marpada

475 posts

Ultimate Geek

#3397360 26-Jul-2025 22:59

It can be a number of things. I assume you are using the right remote user, like `ssh pi@X.X.X.X`, also on MacOS/Linux the permissions of the private key are important, not sure in Windows.

`ssh -v` might give you a hint of what's is wrong. If not check the logs of the sshd server, if you still have access to the pihole.

timmmay

20575 posts

Uber Geek

Trusted

Lifetime subscriber

#3397374 27-Jul-2025 08:34

How about starting again, getting Raspian working with password and key login, then installing Pi Hole docker? That way you can easily run other things on the Pi. Right now my Pi Hole is running Home Assistant, AppDaemon (works with HA), influxdb, grafana, uptime kuma, cloudflare daemon, nginx, pi hole, postgresql, restic for backup, syncthing, trilium-next (like Evernote), file browser (like a basic dropbox which works with cloudflare tunnel for private file sharing), and watchtower.

I can provide a docker-compose file, Nginx config, and I have snippets of code for things like setting up ssh keys for standard users and root. It'd still take a bit of time to get it all working.

mentalinc

3226 posts

Uber Geek

Trusted

#3397375 27-Jul-2025 08:45

Also wondering if it's configured for the key, and failing there, instead of moving on to prompt for a password.

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