Linux

okay I tried that, using -i to specify private key. I get the same thing: blank / blinking cursor. When I use verbose -v flag, I see that in all cases (using -i, the config file, and originally) it ends with these two lines (after about 50 lines) :

debug1: Offering public key: /home/username/.ssh/id_rsa RSA SHA256:j3MUkYzhTrjC6PHkIbre3O(etc) agent
debug1: Server accepts key: /home/username/.ssh/id_rsa RSA SHA256:j3MUkYzhTrjC6PHkIbre3OT(etc) agent

where (etc) is some redacted text. It seems the server is ACCEPTING the key, which is nice. But then it's still a blinking cursor...

FWIW, I've found that the -v flag often doesn't say why it's not using your key, just that it isn't using your key and it has fallen back to password authentication.

It's usually not terribly helpful for figuring out why it's not using your key, just that it's not using your key, which you kind of already know if it's prompting you for a password. lol

The whole point of ssh-agent is to remember your passphrase.

replace passphrase with private key and you're very correct.

passphrases used to login to servers using PasswordAuthentication are not stored in the agent. i might be wrong with technical details on how the private key is actually stored in RAM by the agent, but in the context of ssh passphrases that could be directly used for login to servers, saying the agent stores passphrases is at least a bit misleading.

what you want is:

• use Key authentication, not passwords
• disable passwordauthentication on the server when you have setup and secured (some sort of backup) ssh access with keys instead of passwords.
• if you always want to provide a short password for login, then don't use an agent, i.e. unset that environment variable and check ssh_config
• give your private key a password that fits your needs (average time it shoulf take attackers to guess that password vs your time you need overall to exchange the pubkey on all your servers)
• change the privatekey every time immediately after someone might have had access to the password protected privkey file
• do not give others access to your account on your pc to not have to change your private key too often.

also an idea:

• use a token that stores the private key AND is PIN protected as in it would lock itself upon a few tries with a wrong pin. this way the "password" needed to enter for logins can be minimal while at the same time protecting the private key from beeing copied. but even then one should not let others have access to the same machine (of course not as root) or account (as user, but better not at all) as an unlocked token could also possibly be used to place a second attacker provided key on the server you wanted to protect.

all depends on the level of security you want to achieve. additional TOTP could improve security too (but beware that some authenticator providers might have "sharing" features which could compromise the TOTP token even before its first use.

Not OP but everytime I used the verbose output of ssh it didn't help me one bit. Even adding outrageous verbosity I was still quite confused on what step failed and which didn't.

I'm probably just bad at understanding SSH but i don't know it seems like ssh workflow includes many trial and error until it finds a way to connect.

Imo the verbose output of SSH is often not very helpful if you don't know very well ssh in the first place. Obviously it is still worth a shot and a good advice but don't expect ssh to clearly state what is going on :)