I have a late 2011 MacBook Pro. I've been running 10.8.x. I'm using the Apple branded dual-link DVI adapter to connect an external WQHD monitor (1440p). It was working great with 10.8.
I just installed the 10.9.2 update from the AppStore. During the upgrade, the machine wouldn't even boot with the DVI adapter connected. After figuring that out, the upgrade installed.
Now, when I connect the adapter, the laptop LCD screen goes black (but backlit, so it's not off) and the external monitor doesn't detect a signal. When I remove the thunderbolt cord to the adapter, the display remains black (it doesn't switch back).
If I boot the machine with the adapter connected, the dock never appears and CMD+TAB doesn't show anything. When I remove the adapter at that point, the dock appears.
System Information shows the adapter as detected, but the resolution is shown as "1×1".
EDIT: Here's some info from the system log:
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: Received display connect changed for display 0x4272dc2
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: Found 45 modes for display 0x04272dc2 [33, 12]
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: Received display connect changed for display 0x3f003f
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: build_mode_list_if_needed: No always available modes from IOGraphics [1, 1, 0, 0, 0, 0]
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: mode id 0x00003000, nominal [1 x 1], flags 0x00000000
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: Found 3 modes for display 0x003f003f [0, 0]
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: Display 0x003f003f changed state to online
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: MPSelectMode: Mode number 1 always unavailable for display 0x003f003f
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: complete_connect_change: Error selecting mode 1 for display 0x003f003f
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: Received display connect changed for display 0x3f0040
Mar 24 09:29:51 LM125892-CYTHOM WindowServer[106]: Found 1 modes for display 0x003f0040 [1, 0]
Mar 24 09:30:00 LM125892-CYTHOM com.apple.launchd.peruser.735236149[306] (com.qbix.CalendarStart[768]): Exited with code: 1
Mar 24 09:30:00 LM125892-CYTHOM com.apple.launchd.peruser.735236149[306] (com.qbix.CalendarStart): Throttling respawn: Will start in 10 seconds
Mar 24 09:30:10 LM125892-CYTHOM com.apple.launchd.peruser.735236149[306] (com.qbix.CalendarStart[824]): Exited with code: 1
Mar 24 09:30:12 LM125892-CYTHOM com.apple.launchd[1] (com.teamviewer.service): assertion failed: 13C64: launchd + 40562 [425516B6-9F3E-342F-87B3-EC461EBA6A1A]: 0x10000003
Mar 24 09:30:12 LM125892-CYTHOM WindowServer[106]: CGXGetConnectionProperty: Invalid connection 61699
Mar 24 09:30:12 --- last message repeated 19 times ---
Mar 24 09:30:12 LM125892-CYTHOM WindowServer[106]: CGXOrderWindowList: Invalid window 56 (index 0/1)
Mar 24 09:30:12 LM125892-CYTHOM WindowServer[106]: CGXGetConnectionProperty: Invalid connection 61699
Best Answer
I would probably install the old OS onto an external USB drive to be sure it's not a failure unrelated to the OS.
It's rare that the OS breaks an adapter that was working - even if the change happened at the same time as an OS update. Also, you can usually rule out software by updating to 10.9.3 (in your case) or to the next point update in case there was an error that was caught in the drivers or settings.