Youre trying to do something, what we're not quite sure - you've made a classic XY problem mistake.. You have some task, like "implement auto login expiry if it's on in the prefs table" and you've devised this broken solution (use a computed column/IIF) and have sought help to know why it's broken.. It's not solving the actual core problem.
In transitioning from your current state to one where you're solving the problem, you can consider:
As a view:
CREATE VIEW yourtable_withexpiry AS
SELECT
*,
CASE WHEN [ExpiryDate] IS NULL OR config.[Value] = 1 AND SysDateTimeOffset() < [ExpiryDate] THEN 1 ELSE 0 END AS IsValid
FROM
yourtable
LEFT JOIN
config
ON config.property = 'AutomaticExpiry'
As a trigger:
CREATE TRIGGER trg_withexpiry ON yourtable
AFTER INSERT OR UPDATE
AS
IF NOT EXISTS(select * from Config where Property = 'AutomaticExpiry' and Value = 1)
RETURN;
UPDATE yourtable SET [ExpiryDate] = DATE_ADD(..some current time and suitable offset here..)
FROM yourtable y INNER JOIN inserted i ON y.pk = i.pk;
END;
But honestly, you should be doing this in your front end app. It should be responsible for reading/writing session data and keeping things up to date and kicking users out if they're over time etc.. Using the database for this is, to a large extent, putting business logic/decision processing into a system that shouldn't be concerned with it..
Have your front end language implement a code that looks up user info upon some regular event (like page navigation or other activity) and refreshes the expiry date as a consequence of the activity, only if the expiry date isn't passed. For sure too keep the thing valid if the expiry is set to null if you want a way to have people active forever (or whatever)