--- a/crates/jrsonnet-evaluator/src/obj/mod.rs
+++ b/crates/jrsonnet-evaluator/src/obj/mod.rs
@@ -231,6 +231,7 @@
 struct ObjValueInner {
 	cores: Vec<CcObjectCore>,
 	assertions_ran: Cell<bool>,
+	has_assertions: bool,
 	value_cache: RefCell<FxHashMap<(IStr, CoreIdx), CacheValue>>,
 }
 
@@ -258,6 +259,7 @@
 	static EMPTY_OBJ: ObjValue = ObjValue(Cc::new(ObjValueInner {
 		cores: vec![],
 		assertions_ran: Cell::new(true),
+		has_assertions: false,
 		value_cache: RefCell::default(),
 	}))
 }
@@ -475,10 +477,12 @@
 	pub fn extend_from(&self, sup: Self) -> Self {
 		let mut cores = sup.0.cores.clone();
 		cores.extend(self.0.cores.iter().cloned());
+		let has_assertions = sup.0.has_assertions || self.0.has_assertions;
 		ObjValue(Cc::new(ObjValueInner {
 			cores,
 			value_cache: RefCell::default(),
-			assertions_ran: Cell::new(false),
+			assertions_ran: Cell::new(!has_assertions),
+			has_assertions,
 		}))
 	}
 	// #[must_use]
--- a/crates/jrsonnet-evaluator/src/obj/oop.rs
+++ b/crates/jrsonnet-evaluator/src/obj/oop.rs
@@ -114,6 +114,7 @@
 #[allow(clippy::module_name_repetitions)]
 pub struct ObjValueBuilder {
 	sup: Vec<CcObjectCore>,
+	has_assertions: bool,
 
 	new: OopObject,
 	next_field_index: FieldIndex,
@@ -125,6 +126,7 @@
 	pub fn with_capacity(capacity: usize) -> Self {
 		Self {
 			sup: vec![],
+			has_assertions: false,
 			new: OopObject::new(FxHashMap::with_capacity(capacity), None),
 			next_field_index: FieldIndex::default(),
 		}
@@ -134,6 +136,7 @@
 		self
 	}
 	pub fn with_super(&mut self, super_obj: ObjValue) -> &mut Self {
+		self.has_assertions |= super_obj.0.has_assertions;
 		self.sup.clone_from(&super_obj.0.cores);
 		self
 	}
@@ -143,6 +146,7 @@
 			self.new.assertion.is_none(),
 			"one OopObject can only have one assertion"
 		);
+		self.has_assertions = true;
 		self.new.assertion = Some(CcObjectAssertion::new(assertion));
 		self
 	}
@@ -193,9 +197,11 @@
 		if self.sup.is_empty() {
 			return ObjValue::empty();
 		}
+		let has_assertions = self.has_assertions;
 		ObjValue(Cc::new(ObjValueInner {
 			cores: self.sup,
-			assertions_ran: Cell::new(false),
+			assertions_ran: Cell::new(!has_assertions),
+			has_assertions,
 			value_cache: RefCell::default(),
 		}))
 	}