pfSense+ 23.09 Lenovo Thinkcentre M93P SFF Quadcore i7 dual Raid-ZFS 128GB-SSD 32GB-RAM PCI-Intel i350-t4 NIC, -Intel QAT 8950.
pfSense+ 23.09 VM-Proxmox, Dell Precision Xeon-W2155 Nvme 500GB-ZFS 128GB-RAM PCIe-Intel i350-t4, Intel QAT-8950, P-cloud.

Unless he disabled the antilock rule, once you enable ssh its in the antilock out rule to be allowed.

Maybe didn't actually enable it? Maybe he changed the port from 22? He is has a software firewall on the client he is running blocking it? His pfsense lan IP is not actually 192.168.1.1?

ssh didn't actually start for some reason?

Lots of possible reasons it could be timing out to connect.

edit:
I should test this - is it possible to create a floating rule that blocks the antilock out rule? Hmmm - be right back.

edit2: Nope even putting a floating rule to block doesn't stop antilockout - which is stated on the rules order link
https://docs.netgate.com/pfsense/en/latest/firewall/firewall-rule-processing-order.html

Internal automatic rules (pass and block for various items like lockout, snort, DHCP, etc.)

Are above floating even.. so seems only way you could firewall yourself from ssh on the lan would be to have disabled the antilockout.