Anonymous access to SMB share hosted on Server 2008 R2 Enterprise

You did everything correct with the exception of the local account accessing the share cannot be on both systems. Essentially, if the non-domain account running your application is called "administrator" then you must not have a local account on the domain server named "administrator".

If the username you are using the login with exists on the server but has a different password it will always prompt for the password no matter what guest and anonymous settings you have created.

Try logging in with a username that does not exist anywhere on the server or it's domain.

The other option is the make the password on the stand alone server exactly the same as it is on the identical named user on the domain.

How about mapping a network drive, and utilizing a persistent connection syntax would be something like this.

net use H: \path\to\server\ PASSWORD_CLEAR_TXT /user:domain\user /persistent:yes

if at any time you want to delete it net use h: /delete

Possibly temp workaround . You can create local user account(an give share\ntfs permissions) on the "share server" with same name & password as account used on your "test server" for running app accessing shares.