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Looks like this will work

HttpsOnly = webApp.HttpsOnly.Apply(v => v!.Value),

but I'm still not sure why ClientAffinityEnabled and HttpsOnly behave differently?

That’s a very good question. The duality of nullable types in C# (value vs reference) is getting us here. Maybe we could improve this situation with an extra conversion. Do you mind creating a case in https://github.com/pulumi/pulumi ?

Thanks Mikhail here you go...