I no longer have a Windows server on my net, but here are some ideas to try until a better one comes along:
You didn’t state whether the Windows servers you were logging into were using Active Directory based client login or some other form.
It probably happens because you get logged out of the far end server, and need to log back in. You would have to somehow store your credentials to do that, and if you are connecting to a Windows world they have various ways of doing that.
Here’s a somewhat dated, but probably accurate process. Not sure it still works on all Mac OS’s.
Map a network drive to Mac OS X that re-mounts after system reboot
This method allows you to reboot your Mac and have the mapped network drive / network share automatically connect and remount, appearing on the desktop of OS X or in the Finder sidebar. This is more persistent than the previous method and is helpful for network shares you connect to frequently:
From the Finder, hit Command+K
Enter the path to the network drive you want to map, ie: smb://networkcomputer/networkshare and click ‘Connect’
Enter your login credentials and click “OK”
The drive is now mounted, but continue on to map for system reboot persistence
Now enter into System Preferences, from the Apple menu
Click on ‘Accounts’
Click on “Login Items”
Click on the + button to add another login item
Locate the network drive you previously mounted and click “Add”
Exit out of System Preferences
Your network drive will now be mapped and automatically remounted when you reboot your Mac. Keep in mind that if you leave the network where the mapped share is located, the drive/share will not automatically reconnect until that network is joined again, and the Mac is either rebooted or manually reconnected to the desired network share.
Here is a utility you might want to explore.
https://www.lobotomo.com/products/WinShortcutter/index.html
Hope this helps.
Al