SWITCH on Conditional DATETIME selection help

Hi, 5000 

Thanks for Ritaf1983's concern about this issue.

May I ask what your dataset looks like?
Since you didn't give the dataset for conducting the test, I assumed some data for my own test:

In my tests, your Measure is working fine:

Maybe you can refer to my Measure for modification:

PIT Status2 =
VAR CurrentPIT =
    IFERROR ( SELECTEDVALUE ( 'Z_Point In Time'[PIT Date], TODAY () ), TODAY () )
RETURN
    SWITCH (
        TRUE (),
        CurrentPIT = TODAY (), [Order Line Status1],
        [Order Line Status1] = "Open"
            && CurrentPIT > [Create Date], "Open",
        [Order Line Status1] = "Open"
            && CurrentPIT <= [Create Date], "",
        [Order Line Status1] = "Shipped"
            && CurrentPIT > [Actual Date], "Shipped",
        [Order Line Status1] = "Shipped"
            && CurrentPIT <= [Actual Date]
            && CurrentPIT > [Create Date], "Open",
        [Order Line Status1] = "Shipped"
            && CurrentPIT <= [Actual Date]
            && CurrentPIT <= [Create Date], "",
        "NOT"
    )

I have attached the pbix file below for your reference, I hope it helps.

I hope my suggestions give you good ideas, if you have any more questions, please clarify in a follow-up reply.
Best Regards,
Fen Ling,
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