@D-C 

I made some small changes in the switch configuration like you mentioned. I have 3 AP's, located on the switch on ports 21, 22 and 23. These ports have the MGMT network (10.10.10.x as VLAN 1 untagged, with PVID set to 1) and the other 3 networks, LAN(20), IOT(60) and GUEST(99) are set as tagged. So far so good.

A little bit more detailed info: 

- The omada controller is located virtually (I know, to make it even more difficult to get setup correctly :/) and is connected to the MGMT (management) network (10.10.10.x) 

- The AP was first connected to the LAN network (10.10.20.x) 

At this stage, even though they aren't both in the same network, they could "see" each other in the omada controller(green - CONNECTED) and I can configure the AP.

When I then make the changes in the omada wireless settings and then connect one of the AP's to port 21, the omada controller first gives an error "heartbeat missed", followed bu "disconnected" a little while later. 

To make things even more strange, when I swapped the AP's cable to port 21, It actually worked for a few minutes, I got a IP address in the 10.10.99.x range, I even could browse the web, but after a few minutes, all wireless SSID's are gone. I assume at the same time that the omada controller changes the state of the AP to "disconnected".

I think I am still missing something?

If you need some screenshots, or any more info, please let me know.

  @Houseofdreams_, assuming that you're using DHCP, if you can plug a computer into port 21, do you get a 10.10.10.x address?

  @D-C 

When I use a static 10.10.10.x address I'm connected (lan/internet) when I use DHCP, I don't get a IP address. Strange... This is my "networks" setup in the omada controller. 

Edit: I'm now connected with a patch cable to one of the ports on the switch that are in the MGMT 10.10.10.x network (port 7 on the switch) and also there, with a direct connection, I don't seem to get a IP address from the MGMT network. I'm trying to find out why I don't get DCHP from that network. It's enabled in PFSense, all other networks do get DHCP, so it's not the DCHP service that's buggy.

Strange.

@Houseofdreams_ DHCP services on pfSense are unique to each interface so don't assume it's running on your 10.10.10.x network based on it working on other networks. Most likely it's an issue with the VLAN 1 configuration somewhere between pfSense and the AP.  On the Omada devices that support it, I use DHCP and set the fallback ip so a DHCP issue will not cause problems.

  @D-C 

Got some time to test some things....

Made a ubuntu VM on the esxi box, gave it a MGMT network card, installed it and without a problem, it gets an IP of 10.10.10.100 

So on the esxi box, the DHCP works, I can see it in the DHCP leases table in PFsense. But still, when I connect a laptop for example to one of the 2 assigned MGMT ports on one of the 2 switches (windows laptop, not that this would make any difference) I can do ipconfig / release - ipconfig / renew and it just sits there and after a while it just says that there is no ip address assigned.

From what I can see, the port settings on the switches are also correct. Port 18 on switch 2 is assigned as a untagged System-VLAN (1) with PVID set to 1. The same is done n switch 1 on port 7.

I assume this is correct?

Is there any way that I can "debug" the switch?