Can't SSH into macOS machine until I VNC

I have several M1 Mac Minis running on MacStadium. They are all remotely manageable, so I can SSH and VNC into them with the auth I was given.

From time to time, the following happens:

1. I suddenly notice I cannot SSH into a machine anymore, but I have services running on it, so I know it is up and running.
2. I VNC into the machine, and I’m greeted with the macOS screen requesting my password.
3. I input the password and log in.
4. At this point, I am able to SSH in again into the machine.

After a while, this will happen again, so if I want to recover SSH control over the machine I am forced to repeat the manual VNC login steps.

This is how SSH fails when it does:

OpenSSH_8.1p1, LibreSSL 2.7.3
debug1: Reading configuration data /Users/alexboboc/.ssh/config
debug1: /Users/alexboboc/.ssh/config line 1: Applying options for *
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 47: Applying options for *
debug2: resolve_canonicalize: hostname 207.254.39.221 is address
debug2: ssh_connect_direct
debug1: Connecting to 207.254.39.221 [207.254.39.221] port 22.
debug1: Connection established.
debug1: identity file /Users/alexboboc/.ssh/id_rsa type 0
debug1: identity file /Users/alexboboc/.ssh/id_rsa-cert type -1
debug1: Local version string SSH-2.0-OpenSSH_8.1
debug1: Remote protocol version 2.0, remote software version OpenSSH_8.1
debug1: match: OpenSSH_8.1 pat OpenSSH* compat 0x04000000
debug2: fd 3 setting O_NONBLOCK
debug1: Authenticating to 207.254.39.221:22 as 'administrator'
debug3: hostkeys_foreach: reading file "/Users/alexboboc/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /Users/alexboboc/.ssh/known_hosts:654
debug3: load_hostkeys: loaded 1 keys from 207.254.39.221
debug3: order_hostkeyalgs: prefer hostkeyalgs: [email protected],[email protected],[email protected],ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521
debug3: send packet: type 20
debug1: SSH2_MSG_KEXINIT sent
debug3: receive packet: type 20
debug1: SSH2_MSG_KEXINIT received
debug2: local client KEXINIT proposal
debug2: KEX algorithms: curve25519-sha256,[email protected],ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group16-sha512,diffie-hellman-group18-sha512,diffie-hellman-group14-sha256,diffie-hellman-group14-sha1,ext-info-c
debug2: host key algorithms: [email protected],[email protected],[email protected],ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521,[email protected],[email protected],[email protected],[email protected],ssh-ed25519,rsa-sha2-512,rsa-sha2-256,ssh-rsa
debug2: ciphers ctos: [email protected],aes128-ctr,aes192-ctr,aes256-ctr,[email protected],[email protected]
debug2: ciphers stoc: [email protected],aes128-ctr,aes192-ctr,aes256-ctr,[email protected],[email protected]
debug2: MACs ctos: [email protected],[email protected],[email protected],[email protected],[email protected],[email protected],[email protected],hmac-sha2-256,hmac-sha2-512,hmac-sha1
debug2: MACs stoc: [email protected],[email protected],[email protected],[email protected],[email protected],[email protected],[email protected],hmac-sha2-256,hmac-sha2-512,hmac-sha1
debug2: compression ctos: none,[email protected],zlib
debug2: compression stoc: none,[email protected],zlib
debug2: languages ctos:
debug2: languages stoc:
debug2: first_kex_follows 0
debug2: reserved 0
debug2: peer server KEXINIT proposal
debug2: KEX algorithms: curve25519-sha256,[email protected],ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group16-sha512,diffie-hellman-group18-sha512,diffie-hellman-group14-sha256,diffie-hellman-group14-sha1
debug2: host key algorithms: rsa-sha2-512,rsa-sha2-256,ssh-rsa,ecdsa-sha2-nistp256,ssh-ed25519
debug2: ciphers ctos: [email protected],aes128-ctr,aes192-ctr,aes256-ctr,[email protected],[email protected]
debug2: ciphers stoc: [email protected],aes128-ctr,aes192-ctr,aes256-ctr,[email protected],[email protected]
debug2: MACs ctos: [email protected],[email protected],[email protected],[email protected],[email protected],[email protected],[email protected],hmac-sha2-256,hmac-sha2-512,hmac-sha1
debug2: MACs stoc: [email protected],[email protected],[email protected],[email protected],[email protected],[email protected],[email protected],hmac-sha2-256,hmac-sha2-512,hmac-sha1
debug2: compression ctos: none,[email protected]
debug2: compression stoc: none,[email protected]
debug2: languages ctos:
debug2: languages stoc:
debug2: first_kex_follows 0
debug2: reserved 0
debug1: kex: algorithm: curve25519-sha256
debug1: kex: host key algorithm: ecdsa-sha2-nistp256
debug1: kex: server->client cipher: [email protected] MAC: <implicit> compression: none
debug1: kex: client->server cipher: [email protected] MAC: <implicit> compression: none
debug3: send packet: type 30
debug1: expecting SSH2_MSG_KEX_ECDH_REPLY
debug3: receive packet: type 31
debug1: Server host key: ecdsa-sha2-nistp256 SHA256:1pG80bFeaYfya3iiGhW5tqBuh4Bb26ODlbM2+dbbJpY
debug3: hostkeys_foreach: reading file "/Users/alexboboc/.ssh/known_hosts"
debug3: record_hostkey: found key type ECDSA in file /Users/alexboboc/.ssh/known_hosts:654
debug3: load_hostkeys: loaded 1 keys from 207.254.39.221
debug1: Host '207.254.39.221' is known and matches the ECDSA host key.
debug1: Found key in /Users/alexboboc/.ssh/known_hosts:654
debug3: send packet: type 21
debug2: set_newkeys: mode 1
debug1: rekey out after 134217728 blocks
debug1: SSH2_MSG_NEWKEYS sent
debug1: expecting SSH2_MSG_NEWKEYS
debug3: receive packet: type 21
debug1: SSH2_MSG_NEWKEYS received
debug2: set_newkeys: mode 0
debug1: rekey in after 134217728 blocks
debug1: Will attempt key: /Users/alexboboc/.ssh/id_rsa RSA SHA256:+Wqv4oTz/Sp/OXsfoLWZEhS0DbJB0dTxB14d+5ND1sU explicit agent
debug2: pubkey_prepare: done
debug3: send packet: type 5
debug3: receive packet: type 7
debug1: SSH2_MSG_EXT_INFO received
debug1: kex_input_ext_info: server-sig-algs=<ssh-ed25519,ssh-rsa,rsa-sha2-256,rsa-sha2-512,ssh-dss,ecdsa-sha2-nistp256,ecdsa-sha2-nistp384,ecdsa-sha2-nistp521>
debug3: receive packet: type 6
debug2: service_accept: ssh-userauth
debug1: SSH2_MSG_SERVICE_ACCEPT received
debug3: send packet: type 50
debug3: receive packet: type 51
debug1: Authentications that can continue: publickey,password,keyboard-interactive
debug3: start over, passed a different list publickey,password,keyboard-interactive
debug3: preferred publickey,keyboard-interactive,password
debug3: authmethod_lookup publickey
debug3: remaining preferred: keyboard-interactive,password
debug3: authmethod_is_enabled publickey
debug1: Next authentication method: publickey
debug1: Offering public key: /Users/alexboboc/.ssh/id_rsa RSA SHA256:+Wqv4oTz/Sp/OXsfoLWZEhS0DbJB0dTxB14d+5ND1sU explicit agent
debug3: send packet: type 50
debug2: we sent a publickey packet, wait for reply
debug3: receive packet: type 60
debug1: Server accepts key: /Users/alexboboc/.ssh/id_rsa RSA SHA256:+Wqv4oTz/Sp/OXsfoLWZEhS0DbJB0dTxB14d+5ND1sU explicit agent
debug3: sign_and_send_pubkey: RSA SHA256:+Wqv4oTz/Sp/OXsfoLWZEhS0DbJB0dTxB14d+5ND1sU
debug3: sign_and_send_pubkey: signing using rsa-sha2-512
debug3: send packet: type 50
Connection closed by 207.254.39.221 port 22

It appears that, for some reason, the SSH daemon stops running at some point.