Given this scenario: Dev1 and Dev2 working on Lib.cs. Dev1 checks in Lib.cs to TFS with his changes. A week later Dev2 (w/o Getting Latest) checks in his changes to Lib.cs and is not prompted to fix conflicts. I would assume that because Dev2 did not get the fix conflicts tab that TFS was able to merge the two files. However, we see that Lib.cs was overwritten with Dev2 changes and it looks like no merge was attempted.
Could this be because Dev2 did not perform Get Latest more frequently?