Perhaps you are having problems, because you keep trying to start daemon from the web interface, instead of clicking the big (shiny) connect button?
Most of the suggestions below are simply steps to get you back to default settings
Restart jail
Open gtkui on your windows10 host, connect to deluged in your jail.
Go to Preferences and check that under "Plugins" WebUI is NOT checked. If checked, remove the checkbox.
Go to Preferences and under Daemon change the Daemon port back to default 58846.
You will lose the connection from your gtkui client to deluged on freenas jail.
Restart jail.
Open Connection manager in your gtkui client. Click Add and enter freenas jail ip, username and password for deluged. You don't even have to connect, as the light will turn green and under version you will see 1.3.15.
You can remove the old entry in gtkui clients Connection Manager
Open web-browser on your w10 host and open the web interface on your jail (default jail-ip:8112). Login with the password for deluge-web.
Open "Connection Manager" and click on "Add"
Under Host enter: 127.0.0.1
Under port enter the port that deluged is listening on=58846.
If under status you now see "Online", click on host and then click Connect.
Done.
P.S.
If you don't see Stauts:Online, open "Connection Manager" and click on "Add" again, but this time:
Host 127.0.0.1, port 58846, username: "your username for deluged", password:"your password for deluged"
Deluged allows clients that are running on the same host and under the same user/settings to connect without user/pass.
In your case, deluged and deluge-web are running in the same jail and under the same user, so unless you removed the localhost:yyxxzz:10 line from auth, deluge-web can connect to deluged without user:pass.
I'm gonna write some simplified deluge stuff below (which you probably already know), so forgive me if it comes off arrogant/boring.
Also you don't have to read it.
Deluge is made of:
Deluge Daemon: does everything and allows clients to connect and manage it. All the "torrenting" happens here.
-It is mostly called
deluged
-It talks to clients on port 58846 (default port)
-It talks to peers and trackers and does bittorrent stuff on port 6881 (default port) but we don't care about that right now.
Deluge Clients: They connect to
deluged and manage it. With a client, you can add/remove torrents from deluged, change some deluged setting, etc.
-Clients can connect to deluged from anywhere (over the network).
-One client is a gui client, also called gtkui. You have that working and it connects from your pc to deluged.
-It has it's own settings (gtkui/preferences/Interface)
-There are other clients, like deluge-console but we don't care right now.
Deluge Web Interface:
-It's mostly called deluge-web
-It can run on the same machine/host/jail as deluged or on a different host.
-It's just another client. As long as it knows where deluged is (ip address) and what port it is running on, it can connect.
-It has it's own settings (web interface/preferences/Interface)
P.P.S.
Sorry for spamming this wall of text instead of just helping, but I had 30 minuts to kill
