I am having a very weird problem with my Mikrotik 450G Router. My network setup is as follows:
Ether-1 → WAN Connection to ISP via PPOE-OUT
Ether 2,3,4,5 → Are bridged for Local LAN with DHCP Server running on the bridge interface.
I have a switch-cum-AP connected on Port Ether 2 for WiFi.
I have a Raspberry Pi connected on Port Ether 3 directly to the router running Pi-Hole which is used as my local DNS.
Now the problem is I am unable to SSH to the Pi, when it is connected to Ether 3 on the router. However, if I move the Pi to the switch that is connected to Ether 2 on the Router, everything works fine. I have verified that my SSH is configured properly, multiple times. The web interface and everything else works fine just the SSH will not connect when it is connected directly to the router on ether 3.
MacBook-Pro:~ Kushal$ ssh -v 192.168.88.221 -p1088
OpenSSH_7.7p1, OpenSSL 1.0.2o 27 Mar 2018
debug1: Reading configuration data /usr/local/etc/ssh/ssh_config
debug1: Connecting to 192.168.88.221 [192.168.88.221] port 1088.
debug1: connect to address 192.168.88.221 port 1088: Connection refused
ssh: connect to host 192.168.88.221 port 1088: Connection refused