Erroneous Results from COUNTROWS() in Context-transition

Unless I'm missing something, I'm pretty sure this isn't supposed to happen:

EVALUATE
CALCULATETABLE (
    CALCULATETABLE (
        ADDCOLUMNS (
            VALUES ( Users[User ID] ),
            "Test Expression 1 - CORRECT",
                CALCULATE (
                    CONCATENATEX (
                        FILTER (
                            VALUES ( 'Privilege Conflicts'[Privilege 2 ID] ),
                            'Privilege Conflicts'[Privilege 2 ID]
                                IN VALUES ( Privileges[Privilege ID] )
                        ),
                        'Privilege Conflicts'[Privilege 2 ID],
                        " | "
                    )
                ),
            "Test Expression 2 - INCORRECT",
                CALCULATE (
                    COUNTROWS (
                        FILTER (
                            VALUES ( 'Privilege Conflicts'[Privilege 2 ID] ),
                            'Privilege Conflicts'[Privilege 2 ID]
                                IN VALUES ( Privileges[Privilege ID] )
                        )
                    )
                )
        ),
        CROSSFILTER ( 'Users and Privileges'[Privilege ID], Privileges[Privilege ID], BOTH )
    ),
    Users[User ID] IN { 102, 103 }
)

Results:

Notice how, for User ID = 102, the results in the test expressions are inconsistent, despite the fact that they are semantically basically the same.

For reference, note that the following produces expected results:

EVALUATE
CALCULATETABLE(
    CALCULATETABLE(
        {
            ( 
	            
	            -- Test Expression 1 - CORRECT
	            
	            CALCULATE(
	                CONCATENATEX(
	                    FILTER(
	                        VALUES( 'Privilege Conflicts'[Privilege 2 ID] ),
	                        'Privilege Conflicts'[Privilege 2 ID]
	                            IN VALUES( Privileges[Privilege ID] )
	                    ),
	                    'Privilege Conflicts'[Privilege 2 ID],
	                    " | "
	                ),
	                Users[User ID] = 102
	            ),
	            
	            -- Test Expression 2 - CORRECT (inconsistent with prior query)
	            
	            CALCULATE(
	                COUNTROWS(
	                    FILTER(
	                        VALUES( 'Privilege Conflicts'[Privilege 2 ID] ),
	                        'Privilege Conflicts'[Privilege 2 ID]
	                            IN VALUES( Privileges[Privilege ID] )
	                    )
	                ),
	                Users[User ID] = 102
	            ) 
            )
        },
        CROSSFILTER ( 'Users and Privileges'[Privilege ID], Privileges[Privilege ID], BOTH )
    ),
    Users[User ID] IN { 102, 103 }
)

Results:

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It appears that something might not be functioning correctly between the context-transition and COUNTROWS(), but not fully sure.

marcorusso Jeffreywang 

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Power BI version: 2.139.2054.0

Data model: