MacOS – How to fix things when Catalina will not connect to smb shares

If you can't get SMB working, try AFP. You can run both side-by-side, and use SMB on your Windows and AFP on OS X.

To set up AFP on your Raspberry Pi, you can use the following command:

sudo apt-get install netatalk

This will install Netatalk on your RPi, and following successful installation, the RPi should automatically show in the Shared section in Finder and the Network neighbourhood (⌘⇧K):

^{If not, you can connect manually by pressing ⌘K and typing afp:// followed by the IP address of your RPi.}

Not certain I understand the context of your question, so let's try this first:

This has worked for me:

1. Mount the SMB/CIFS share using Finder's Go, Connect to Server....
2. If prompted for credentials, and given the option, store those credentials in the Keychain
3. Open System Preferences, Users and Groups; select the Login Items tab near the top
4. Click the + button at the bottom of the list of login items to "add" an item.
5. This will produce a new Finder window that allows you to select an item. Simply navigate to the mounted SMB/CIFS share from the Sidebar, select/highlight the SMB/CIFS share of interest, then click the Add button in the bottom right of the Finder window.

This should dismiss the Finder window, and now the share should be mounted at each login. Let us know if this doesn't work/isn't what you needed.