diff --git a/tslang/include/TypeScript/LowerToLLVM/UnaryBinLogicalOrHelper.h b/tslang/include/TypeScript/LowerToLLVM/UnaryBinLogicalOrHelper.h
index 4d0b119b3..a5dc95d2a 100644
--- a/tslang/include/TypeScript/LowerToLLVM/UnaryBinLogicalOrHelper.h
+++ b/tslang/include/TypeScript/LowerToLLVM/UnaryBinLogicalOrHelper.h
@@ -229,7 +229,10 @@ mlir::Value LogicOp(Operation *binOp, SyntaxKind op, mlir::Value left, mlir::Typ
                 return cmpOp;
             }
 
-            return LogicOp<StdIOpTy, V1, v1, StdFOpTy, V2, v2>(binOp, op, left, baseType, right, rightType, builder, typeConverter, compileOptions);
+            // the union is the right operand, so it is the right type that becomes its base type:
+            // passing the base type as the left type and the union again as the right one came
+            // straight back here, until the compiler's stack ran out (`opaque != (opaque | null)`)
+            return LogicOp<StdIOpTy, V1, v1, StdFOpTy, V2, v2>(binOp, op, left, leftType, right, baseType, builder, typeConverter, compileOptions);
         }
 
         // excluded string
diff --git a/tslang/test/tester/CMakeLists.txt b/tslang/test/tester/CMakeLists.txt
index f48ed6eed..40a5aa6b4 100644
--- a/tslang/test/tester/CMakeLists.txt
+++ b/tslang/test/tester/CMakeLists.txt
@@ -413,6 +413,7 @@ tslang_add_test(NAME test-compile-00-optional-number-compare COMMAND test-runner
 tslang_add_test(NAME test-compile-00-optional-loose-null COMMAND test-runner "${PROJECT_SOURCE_DIR}/test/tester/tests/00optional_loose_null.ts")
 tslang_add_test(NAME test-compile-00-union-nullable-array COMMAND test-runner "${PROJECT_SOURCE_DIR}/test/tester/tests/00union_nullable_array.ts")
 tslang_add_test(NAME test-compile-00-union-nullable-value COMMAND test-runner "${PROJECT_SOURCE_DIR}/test/tester/tests/00union_nullable_value.ts")
+tslang_add_test(NAME test-compile-00-opaque-nullable-compare COMMAND test-runner "${PROJECT_SOURCE_DIR}/test/tester/tests/00opaque_nullable_compare.ts")
 tslang_add_test(NAME test-compile-00-union-value-equality COMMAND test-runner "${PROJECT_SOURCE_DIR}/test/tester/tests/00union_value_equality.ts")
 tslang_add_test(NAME test-compile-00-strict-equals-mismatched-types COMMAND test-runner "${PROJECT_SOURCE_DIR}/test/tester/tests/00strict_equals_mismatched_types.ts")
 tslang_add_test(NAME test-compile-00-any-number-compare COMMAND test-runner "${PROJECT_SOURCE_DIR}/test/tester/tests/00any_number_compare.ts")
@@ -937,6 +938,7 @@ tslang_add_test(NAME test-jit-00-optional-number-compare COMMAND test-runner -ji
 tslang_add_test(NAME test-jit-00-optional-loose-null COMMAND test-runner -jit "${PROJECT_SOURCE_DIR}/test/tester/tests/00optional_loose_null.ts")
 tslang_add_test(NAME test-jit-00-union-nullable-array COMMAND test-runner -jit "${PROJECT_SOURCE_DIR}/test/tester/tests/00union_nullable_array.ts")
 tslang_add_test(NAME test-jit-00-union-nullable-value COMMAND test-runner -jit "${PROJECT_SOURCE_DIR}/test/tester/tests/00union_nullable_value.ts")
+tslang_add_test(NAME test-jit-00-opaque-nullable-compare COMMAND test-runner -jit "${PROJECT_SOURCE_DIR}/test/tester/tests/00opaque_nullable_compare.ts")
 tslang_add_test(NAME test-jit-00-union-value-equality COMMAND test-runner -jit "${PROJECT_SOURCE_DIR}/test/tester/tests/00union_value_equality.ts")
 tslang_add_test(NAME test-jit-00-strict-equals-mismatched-types COMMAND test-runner -jit "${PROJECT_SOURCE_DIR}/test/tester/tests/00strict_equals_mismatched_types.ts")
 tslang_add_test(NAME test-jit-00-any-number-compare COMMAND test-runner -jit "${PROJECT_SOURCE_DIR}/test/tester/tests/00any_number_compare.ts")
@@ -2178,6 +2180,7 @@ set(TSLANG_CORPUS
     typeGuardOfFormTypeOfBoolean.ts
     types_vs_interfaces.ts
     00any_number_compare.ts
+    00opaque_nullable_compare.ts
     )
 
 # the default model runs these ahead of time only, so the other models do too
diff --git a/tslang/test/tester/tests/00opaque_nullable_compare.ts b/tslang/test/tester/tests/00opaque_nullable_compare.ts
new file mode 100644
index 000000000..f94441f29
--- /dev/null
+++ b/tslang/test/tester/tests/00opaque_nullable_compare.ts
@@ -0,0 +1,61 @@
+// Comparing an Opaque with an `Opaque | null` overflowed the compiler's stack (0xC00000FD, no
+// message): the comparison's lowering kept calling itself with the same operand types.
+
+class State {
+    current: Opaque | null;
+
+    constructor() {
+        this.current = null;
+    }
+
+    set(next: Opaque): boolean {
+        if (next != this.current) {
+            this.current = next;
+            return true;
+        }
+
+        return false;
+    }
+}
+
+class Item {
+    id = 1;
+}
+
+function sameOpaque(a: Opaque, b: Opaque | null) {
+    return a == b;
+}
+
+function sameOpaqueReversed(a: Opaque | null, b: Opaque) {
+    return a == b;
+}
+
+function sameItem(a: Item, b: Item | null) {
+    return a === b;
+}
+
+function differentItem(a: Item, b: Item | null) {
+    return a !== b;
+}
+
+function main() {
+    const s = new State();
+    const h = <Opaque>new Item();
+    const g = <Opaque>new Item();
+
+    assert(s.set(h), "first set binds");
+    assert(!s.set(h), "same handle again is skipped");
+    assert(s.set(g), "another handle binds");
+
+    assert(sameOpaque(h, h), "h == h");
+    assert(!sameOpaque(h, g), "h == g");
+    assert(!sameOpaque(h, null), "h == null");
+    assert(sameOpaqueReversed(h, h), "h == h (union on the left)");
+
+    const item = new Item();
+    assert(sameItem(item, item), "item === item");
+    assert(!sameItem(item, null), "item === null");
+    assert(differentItem(item, new Item()), "item !== other");
+
+    print("done.");
+}