Why does the Basic filter editor sometimes disable itself?

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The basic editor can only represent a subset of OData v4 syntax (comparisons, the supported string functions, parentheses, and/or). If you write or import an expression that uses constructs outside that subset, the editor preserves the expression but disables Basic mode because round-tripping would silently drop information. Simplify the expression in the OData editor to re-enable Basic. See Filter rows.