Share Mac Files (Yosemite) with Windows

I had a similar issue and this post solved it for me:

https://discussions.apple.com/message/26964292#26964292

It may be the same discussion that Tetsujin references, but the setting to use is NOT "Send LM & NTLM - use NTLMv2 session security if negotiated" -- you should use "Send NTLMv2 response only". After I made that change, I connected to the share, put in my Mac username & pwd, and it connected.

The Windows machine generates this error -
logon failure: unknown username or password OS X
& re-presents the login page. No amount of credential-checking/switching seems to work.

It appears that there is a Console error generated on the Mac at the same time as the Windows machine tries to connect -
od failed with 2 proto=ntlmv1-with-v2-session

Things to try...

• (a) turn samba off and on again in sharing…

  System Prefs > Sharing > File Sharing > Options…

  

• (b) change the local security policy on your PC.

  1. Click Start
  2. Click Control Panel
  3. Click System and Maintenance
  4. Click Administrative Tools
  5. Double-Click Local Security Policy
  6. In the left pane, click the triangle next to Local Policy
  7. In the left pane, click Security Options
  8. In the right pane near the bottom, double-click "Network security: LAN manager authentication level"

  Then try one or both of these options. The 2nd worked for me.

  9. Click the drop-down box, and try either
     "Send LM & NTLM - use NTLMv2 session security if negotiated" or
     "Send NTLMv2 response only"
  10. Click OK

Sources:
https://discussions.apple.com/thread/6613032
http://www.jimmah.com/vista/net/ntlm.aspx

I have exactly the same error you described and have been trying to fix sharing files between Windows XP and Mac Yosemite for a week. I will share my findings with you hoping we might find the answer.

Error Message:
This is what appears in the Mac's console every time a Windows XP machine tries to access it. It then asks for the password again and again showing the same error.

 digest-request: init request
 digest-request: init return domain: [Mac] server: [Mac] indomain was: <NULL>
 digest-request: uid=0
 digest-request: od failed with 2 proto=ntlmv1-with-v2-session
 digest-request: user=[Mac]\[User]
 digest-request: kdc failed with 36150275 proto=unknown
 digest-request: guest failed with -1561745590 proto=ntlmv1-with-v2-session

Probable Cause:
When Apple released Mac OSX 10.10 Yosemite it changed the default file sharing protocol to SMB3 but they say that they still support AFP, SMB2 and SMB1 (Windows XP only uses SMB1). In order to have done this they must have fixed their previous buggy implementation of SMB and therefore must have changed lots of code, probably messing up the Windows XP file sharing in the process.

Things I Have Tried:
You may try them as well and see if you get a different result.

• Turning sharing On and Off from the Mac
• Creating a new Administrator User and Sharing Only User
• Repairing permissions with Disk Utility
• Turning off all firewalls (Windows and Mac)
• Activating Windows File Sharing in Sharing Options
• Deactivating AFP File Sharing in Sharing Options
• Changing the Local Security Policy to "Send LM & NTLM - use NTLMv2 session security if negotiated"
• Connecting using IP address
• Changing the Mac's NetBIOS Name
• Setting the Mac's WINS Workgroup Name in Network Settings

Things I Have Not Tried:
I really do not want to do this but will have to if I don't find any other solution.

• Reinstalling Mac OSX 10.10 Yosemite
• Installing custom SMB Server: http://eduo.info/apps/smbup

I hope this helps you and that we can find a solution for the problem. Please let me know if you make any progress.