I have done a bit of research on this and it might be something that has been around for a while. Is this still a known bug when using widgets and a dedicated server model?
If it is not something that is already being addressed, I would be happy to share the test project that generated it.
[2015.03.18-17.59.55:226][ 0]LogLinker:Warning: Can't find file '/Script/UMGEditor'
[2015.03.18-17.59.55:226][ 0]LogUObjectGlobals:Warning: Failed to load '/Script/UMGEditor': Can't find file '/Script/UMGEditor'
[2015.03.18-17.59.55:227][ 0]LogLinker:Warning: Can't find file for asset '/Script/UMGEditor' while loading NULL.
[2015.03.18-17.59.55:227][ 0]LogUObjectGlobals:Warning: Failed to load '/Script/UMGEditor': Can't find file for asset '/Script/UMGEditor' while loading NULL.
[2015.03.18-17.59.55:228][ 0]LogLinker:Warning: Can't find file '/Script/UMGEditor'
[2015.03.18-17.59.55:228][ 0]LogUObjectGlobals:Warning: Failed to load '/Script/UMGEditor': Can't find file '/Script/UMGEditor'
[2015.03.18-17.59.55:229][ 0]LogLinker:Warning: Can't find file for asset '/Script/UMGEditor' while loading NULL.
[2015.03.18-17.59.55:229][ 0]LogUObjectGlobals:Warning: Failed to load '/Script/UMGEditor': Can't find file for asset '/Script/UMGEditor' while loading NULL.
[2015.03.18-17.59.55:230][ 0]LogLinker:Warning: Can't find file '/Script/UMGEditor'
[2015.03.18-17.59.55:230][ 0]LogUObjectGlobals:Warning: Failed to load '/Script/UMGEditor': Can't find file '/Script/UMGEditor'
[2015.03.18-17.59.55:230][ 0]LogLinker:Warning: Can't find file for asset '/Script/UMGEditor' while loading NULL.
[2015.03.18-17.59.55:231][ 0]LogUObjectGlobals:Warning: Failed to load '/Script/UMGEditor': Can't find file for asset '/Script/UMGEditor' while loading NULL.
[2015.03.18-17.59.55:231][ 0]LogLinker:Warning: Can't find file '/Script/UMGEditor'
[2015.03.18-17.59.55:232][ 0]LogUObjectGlobals:Warning: Failed to load '/Script/UMGEditor': Can't find file '/Script/UMGEditor'
[2015.03.18-17.59.55:232][ 0]LogLinker:Warning: Can't find file for asset '/Script/UMGEditor' while loading NULL.
[2015.03.18-17.59.55:233][ 0]LogUObjectGlobals:Warning: Failed to load '/Script/UMGEditor': Can't find file for asset '/Script/UMGEditor' while loading NULL.
[2015.03.18-17.59.55:233][ 0]LogWindows:Error: Windows GetLastError: The operation completed successfully. (0)
[2015.03.18-17.59.57:915][ 0]LogWindows: === Critical error: ===
Assertion failed: Object [File:D:\BuildFarm\buildmachine_++depot+UE4-Releases+4.7\Engine\Source\Runtime\CoreUObject\Public\UObject\UObjectAnnotation.h] [Line: 573]