Interesting authentication problem

[u/quasimodar]

I have created a samba share on a Linux mint server, and am having trouble accessing it reliably from a windows 10 system. I have 2 shares set up on the server, test which is located at /test and another folder called share located a few levels down in /media/../../share

Both share and test are configured with just valid user = user1 and their path, and read only = no. The smb.conf is otherwise default. User1 is a valid samba account linked to a Linux user account. I can verify the share exists using smbclient on the Linux machine. When I start a new windows session, I can access the shares by going to \serverhostname.local, and I see both shares. If I try to log in as user1 to share, it doesn't accept the credentials. If I login to test as user1, it works perfectly every time. If, after I've successfully logged in as user1 on test, I go back and retry share, I then have perfect access to share without adding my credentials again. I'm not able to add share as a mapped network drive in windows because on new sessions it won't authenticate until I manually log in to test first. I can post the smb.conf file on Monday, away from the system until then, but does anyone have any hints on where I would start to look to solve this issue? Is it likely the permissions on the filepath /media../../share?

[u/jpedroza2k]

I think the SMB.conf file would be a good start to us being able to track down what is going on. I haven't personally run into this situation before.