I presume you're trying to find out why a share in CMN does not show as mounted, even though it is mounted, right?

So for CMN to identify a mount as the mount you've setup in CMN it will look for server name (name of IP address), username, and path.
You can see this info in Terminal when entering the command "mount". It will list a few lines (some of those are local disk which usually with /dev/disk), and the last lines (if any) will list the network share.

For example:

~ $ mount
/dev/disk3s3s1 on / (apfs, sealed, local, read-only, journaled)
devfs on /dev (devfs, local, nobrowse)
/dev/disk3s6 on /System/Volumes/VM (apfs, local, noexec, journaled, noatime, nobrowse)
/dev/disk3s4 on /System/Volumes/Preboot (apfs, local, journaled, nobrowse)
/dev/disk3s2 on /System/Volumes/Update (apfs, local, journaled, nobrowse)
/dev/disk1s2 on /System/Volumes/xarts (apfs, local, noexec, journaled, noatime, nobrowse)
/dev/disk1s1 on /System/Volumes/iSCPreboot (apfs, local, journaled, nobrowse)
/dev/disk1s3 on /System/Volumes/Hardware (apfs, local, journaled, nobrowse)
/dev/disk3s1 on /System/Volumes/Data (apfs, local, journaled, nobrowse, protect)
map auto_home on /System/Volumes/Data/home (autofs, automounted, nobrowse)
//admin@192.168.1.100/Someshare on /Volumes/Someshare (smbfs, nodev, nosuid, mounted by hans)
//admin@192.168.1.101/AnotherShare on /Volumes/AnotherShare (smbfs, nodev, nosuid, mounted by hans)

Here the last 2 lines identify user (admin), server name (192.168.1.100 and 192.168.1.101) and paths (Someshare and Anothershare).

These values should match your share definitions for CMN to recognize them as such.
Do you see any discrepancies between mount output and CMN share definitions?

Please note that other applications may mount shares as well - for example Finder and such.

Feel free to post the mount output and matching CMN share definitions here. (mask passwords)

Well, actually there are several issues I'm trying to solve, but let's start with this one first:

• Clicking on this entry in the CMN menu successfully mounts the drive, but the does not display as connected
• In the Share definitions, the "Test Mount" button is enabled, the "Test Unmount" button is disabled

I'm assuming that both symptoms are because CMN does not detect/recognize the mount.

The mount command displays as the last line:

//michael@magnas/backup_macbook on /Users/michael/MountPoints/backup_macbook (smbfs, nodev, nosuid, mounted by michael)

It is defined in CMN as:

Server Address: magnas

Path: backup_macbook

Domain: (empty)

Your assumption is correct. Both issues happen because CMN for some reason does not recognize the mount.

I assume server address, path, and username are all identical (spelled with all small characters)?
Can you test this by replacing the servername (magnas) for its IP address (eg. 192.168.1.100 or something like that)?

Kind-a odd that CMN doesn't detect this.

Replaced magnas by it's IP address and confirmed that username and path are in lowercase. The same behavior persists.

We must be overlooking something simple. Let's see if we can find out 😊 

Alright, before you mount you share, could you open the log window (*), click "Clear", and mount the share?
Also: you'll find a "Tools" button in the log window, which opens a menu. There you can select "List Share Details" - "All Shares".

Right click the log window, and select "Copy All".

You can now paste this in a text editor, and if needed remove sensitive information (maybe change/remove passwords or entries that could be accessed from the Internet, like a webserver for example).

Either post it here as an attachment, or a code (use the "<>" button here).

* you can open the log by opening the share definitions, at the bottom there will be an "Open Log" button.

Log window after pressing [Test Mount]:

12:27:06 │ Mount requested for: "MagNas Backup"
12:27:06 │ - Max Attempts  = 1
         │   Attempts Left = -1
         │   Last Attempt  = n/a
12:27:06 │ - Doing default short mount delay (1 second)
12:27:07 │ - Starting mount background task
12:27:07 │ - RETRY MOUNT TIMER: Started 1 minute timer for remount attempts
12:27:07 │ - Enabled timer for potential extra mount attempts
12:27:07 │ - Thread started

12:27:09 │ Mount status update:
         │ Mount/Open Networkshare feedback (SystemDefault): 
         │ Mount attempt with Calling Apple NetFS API:
         │ 
         │ - LOGIN: Username and Password known - User login with hidden window
         │   URL: smb://192.168.1.80/backup_macbook
         │   Mount directory: macOS will mount against a mount directory in "/Users/michael/MountPoints"
         │ - Mount succesfull - API did not return an Error code, wait for confirmation

12:27:09 │ Thread - Calling for forced status update (only shows results if something changed)

12:27:09 │ System Mount Callback: "/Users/michael/MountPoints/backup_macbook"

12:27:09 │ Thread - Calling for forced status update (only shows results if something changed)

12:27:09 │ -- STATUS UPDATE - THREAD CALLBACK ------------------------------------------------
         │ 
12:27:09 │ Update type
         │  - Initial read     : -
         │  - Timed Interval   : -
         │  - Get Network info : -
         │  - Forced Update    : YES
         │ 
         │ Status Interval     : 10000 milliseconds
         │ Interval Interrupts : 500 milliseconds
         │ Failed mount after  : 30000 milliseconds
         │ 
         │ Default gateway     : 192.168.1.1 (MAC: 00:00:00:00:00:0000:00:00:00:00:00)
         │ 
12:27:09 │ - Mount Status Updated: Counted 1 active share(s)
12:27:09 │ - Matched 0 Network shares. (1 unknown)
12:27:09 │ 
         │ -- STATUS UPDATE - COMPLETED ------------------------------------------------------
12:27:09 │ - RETRY MOUNT TIMER: Stopping timer
12:27:09 │ - RETRY MOUNT TIMER: Quiting, nothing left to retry, and no Fallback servers left either
12:27:09 │ - Updating "Mount onAppear" list
12:27:09 │ - Updating "Mount onAppear" list

12:27:09 │ Updating Tray Menu

12:29:29 │ Updating Tray Menu

12:29:42 │ NETWORK SHARE "MagNas Backup"
         │ -----------------------------
         │ ShareGUID           : {EB002F84-78BA-411F-C241-34A91DB336B0}
         │ Enabled             : TRUE
         │ AutoMenuTitle       : FALSE
         │ 
         │ ShareType           : SMB
         │ RevealOnMount       : FALSE
         │ 
         │ URL                 : 192.168.1.80
         │ RemotePath          : backup_macbook
         │ Port                : 0
         │ 
         │ MountStyle          : SystemDefault
         │ UseCustomPath       : Yes
         │ CustomMountPath     : /Users/michael/MountPoints
         │ CustomIsMountPoint  : Yes
         │ 
         │ Domain              : 
         │ CMDOptions          : 
         │ WebDavUseSSL        : TRUE
         │ 
         │ UseLogin            : TRUE
         │ Username            : *****
         │ Password            : *****
         │ 
         │ UseFallbackServer   : No
         │ FallbackServerGUID  : N/A
         │ 
         │ AutoMountOptions    : At App Startup     : TRUE
         │                       On Network Change  : TRUE
         │                       On Server Appeared : FALSE
         │ AutoMountGateway    : TRUE
         │ AutoMountGatewayIP  : 192.168.2.254
         │ AutoMountGatewayMAC : 7C:16:89:E7:25:07
         │ 
         │ MountAttempts       : 1
         │ MountAttemptsLeft   : 0
         │ LastMountAttempt    : 12:27:06
         │ 
         │ AutoMountForceStop  : FALSE
         │ UseMountDelay       : No
         │ MountDelay          : 30 seconds
         │ UseAutoRunScript    : No
         │ AutoRunScript       : N/A
         │ PingBeforeMount     : TRUE
         │ 
         │ WakeOnLAN           : FALSE
         │ WOLMac              : 00:00:00:00:00:00
         │ WOLBroadcast        : 255.255.255.255
         │ WOLDelay            : 10 seconds
         │ WOLPort             : 9
         │ 
         │ Mounted             : FALSE
         │ WasMounted          : FALSE
         │ MountedPath         : 
         │ MountedBeforeSleep  : FALSE
         │ PID (SSH)           : N/A
         │ 

12:32:27 │ Log window: Hiding

12:32:27 │ Log window: Hiding

12:32:27 │ Updating Tray Menu

12:32:30 │ Updating Tray Menu

12:32:30 │ Log window: Showing

12:32:30 │ Updating Tray Menu

The mount is successful however the  [Test Unmount] button remains disabled and the icon in the dropdown also remains unchanged (displaying unmounted).

I have to say that I have not found a reason yet why this doesn't work on your setup.

Can you do the same, and in the log window use Tools - Terminal Tools - Show "mount" output?

Show show a "mount" dump

It's weird that CMN isn't picking it up. 🤯 
I really would like to figure out what is causing this though.

Again apologies for the late reply.

TERMINAL:

/dev/disk3s1s1 on / (apfs, sealed, local, read-only, journaled)
devfs on /dev (devfs, local, nobrowse)
/dev/disk3s6 on /System/Volumes/VM (apfs, local, noexec, journaled, noatime, nobrowse)
/dev/disk3s2 on /System/Volumes/Preboot (apfs, local, journaled, nobrowse)
/dev/disk3s4 on /System/Volumes/Update (apfs, local, journaled, nobrowse)
/dev/disk1s2 on /System/Volumes/xarts (apfs, local, noexec, journaled, noatime, nobrowse)
/dev/disk1s1 on /System/Volumes/iSCPreboot (apfs, local, journaled, nobrowse)
/dev/disk1s3 on /System/Volumes/Hardware (apfs, local, journaled, nobrowse)
/dev/disk3s5 on /System/Volumes/Data (apfs, local, journaled, nobrowse, protect)
map auto_home on /System/Volumes/Data/home (autofs, automounted, nobrowse)
/dev/disk4s1 on /Volumes/VERBATIM (exfat, local, nodev, nosuid, noowners)
//michael@192.168.1.80/backup_macbook on /Users/michael/MountPoints/backup_macbook (smbfs, nodev, nosuid, mounted by michael)

Could you try this:

Mount the share and then go to the Log window:

• Click the "Clear" button
• Click the "Tools" button, and select "Raw status dumps in log" (so its checked)
• Click the "Tools" button again, and select "Force one time status update"
• Now right click the log window and click "Copy All" and paste it here (ideally formatted as code by using the "<>" in the editor here)

I'm curious what the raw data will show (I had completely forgotten that I had build that in 😣 ).

Also worth a try, but not required; Since you're using the "Commandline" mount style, could you try and see if this happens with the "System Call" mount style (under Advanced Options of the share definition)?

p.s. thanks again for offering remote debugging. Unfortunately, I'd have to install most of my dev tools as well and code.

13:34:53 │ -- STATUS UPDATE - THREAD CALLBACK ------------------------------------------------
         │ 
13:34:53 │ - RAW DUMP:  -> Server     : 192.168.1.80 (//michael@192.168.1.80/backup_macbook)
         │     Port       : (default)
         │     Path       : /backup_macbook
         │     User       : michael
         │     Mountpoint : /Users/michael/MountPoints/backup_macbook
         │     MountType  : SMB (smbfs - 24)
         │   RAW mntfromname : //michael@192.168.1.80/backup_macbook
         │   RAW mountpoint  : /Users/michael/MountPoints/backup_macbook
         │   RAW fstypename  : smbfs
         │ 
13:34:53 │ Update type
         │  - Initial read     : -
         │  - Timed Interval   : YES
         │  - Get Network info : -
         │  - Forced Update    : -
         │ 
         │ Status Interval     : 10000 milliseconds
         │ Interval Interrupts : 500 milliseconds
         │ Failed mount after  : 30000 milliseconds
         │ 
         │ Network             : No network available
         │ 
13:34:53 │ - Mount Status Updated: Counted 1 active share(s)
13:34:53 │ - Looking for a match for:
         │     Share type : stSMB
         │     Server     : 192.168.1.80
         │     Port       : 
         │     Full path  : 
         │     Path       : /backup_macbook
         │     User       : *****
         │     Mountpoint : /Users/michael/MountPoints/backup_macbook
         │     PID        : 0
13:34:53 │ - Matched 0 Network shares. (1 unknown)
13:34:53 │ 
         │ -- STATUS UPDATE - COMPLETED ------------------------------------------------------
13:34:53 │ - Updating "Mount onAppear" list

13:34:53 │ Updating Tray Menu

13:35:12 │ Thread - Calling for forced status update (only shows results if something changed)

13:35:12 │ -- STATUS UPDATE - THREAD CALLBACK ------------------------------------------------
         │ 
13:35:12 │ - RAW DUMP:  -> Server     : 192.168.1.80 (//michael@192.168.1.80/backup_macbook)
         │     Port       : (default)
         │     Path       : /backup_macbook
         │     User       : michael
         │     Mountpoint : /Users/michael/MountPoints/backup_macbook
         │     MountType  : SMB (smbfs - 24)
         │   RAW mntfromname : //michael@192.168.1.80/backup_macbook
         │   RAW mountpoint  : /Users/michael/MountPoints/backup_macbook
         │   RAW fstypename  : smbfs
         │ 
13:35:12 │ Update type
         │  - Initial read     : -
         │  - Timed Interval   : -
         │  - Get Network info : -
         │  - Forced Update    : YES
         │ 
         │ Status Interval     : 10000 milliseconds
         │ Interval Interrupts : 500 milliseconds
         │ Failed mount after  : 30000 milliseconds
         │ 
         │ Network             : No network available
         │ 
13:35:12 │ - Mount Status Updated: Counted 1 active share(s)
13:35:12 │ - Looking for a match for:
         │     Share type : stSMB
         │     Server     : 192.168.1.80
         │     Port       : 
         │     Full path  : 
         │     Path       : /backup_macbook
         │     User       : *****
         │     Mountpoint : /Users/michael/MountPoints/backup_macbook
         │     PID        : 0
13:35:12 │ - Matched 0 Network shares. (1 unknown)
13:35:12 │ 
         │ -- STATUS UPDATE - COMPLETED ------------------------------------------------------
13:35:12 │ - Updating "Mount onAppear" list

13:35:12 │ Updating Tray Menu

The Mount Style is actually set to "System Call". I have now set it to "Commandline" but do not see a difference.

Honestly, I'm a little on a loss here ... I've got no clue why its not picking this up ... welllll ... now I see the "Network : No network available" message. Now I did see in another message that you default gateway had an IP of 0.0.0.0, which is definitely not "standard", and suggests CMN doesn't see a network. I think you mentioned using a VPN? Not sure how that relates to the issue.

If you run this in Terminal, what do you get as a response?

ifconfig | grep -m 1 "status: active"

It should say something like this: (meaning: it found the first line that had this text in it)

	status: active

If you do not get this, then maybe you could paste the "ifconfig" here?
Or: test and see if the share is recognized when the Mac is connected to a regular network (ethernet or WiFi, just not over a VPN).

At the moment I am NOT connected to a VPN and the command indeed shows "status: active".

The issues occur when I am NOT on VPN. When I connect to VPN, I cannot access my local network so, as expected, CMN reports a network change and the option to "Disconnect all".

Ah OK - sorry, I wasn't aware.
P.s. with a VPN connection, depending how you configured it, you can still set it up to see devices in your local network (if connected).

Anyhoo ... I was curious why CMN says that there is no network. It will say that when there is no default gateway, which can be found like so:

route -n get default

... it should say something like this in your case (of course that last "1" can be a different number)

   route to: default
destination: default
       mask: default
    gateway: 192.168.1.1
  interface: en7
      flags: <UP,GATEWAY,DONE,STATIC,PRCLONING,GLOBAL>
 recvpipe  sendpipe  ssthresh  rtt,msec    rttvar  hopcount      mtu     expire
       0         0         0         0         0         0      1500         0 

However, for some reasons CMN gets a blank result back. can you try this?

So, the icon does not appear when booting your Mac connected to your home network, before or after you've used VPN?
I'm so not getting it haha - but I do want to find out!

Command output:

   route to: default
destination: default
       mask: default
    gateway: 192.168.1.1
  interface: en9
      flags: <UP,GATEWAY,DONE,STATIC,PRCLONING,GLOBAL>
 recvpipe  sendpipe  ssthresh  rtt,msec    rttvar  hopcount      mtu     expire
       0         0         0         0         0         0      1500         0

I have never seen the icon showing as "connected' and I have never seen the [Test Unmount] button (on the share definitions screen) enabled.