diff --git a/hclsyntax/expression_ops.go b/hclsyntax/expression_ops.go
index 23b307d8..4e537d72 100644
--- a/hclsyntax/expression_ops.go
+++ b/hclsyntax/expression_ops.go
@@ -41,7 +41,7 @@ var (
 				if rhs.IsKnown() && rhs.True() {
 					return cty.True
 				}
-				return cty.UnknownVal(cty.Bool)
+				return cty.UnknownVal(cty.Bool).RefineNotNull()
 			}
 
 			return cty.NilVal
@@ -60,7 +60,7 @@ var (
 				if rhs.IsKnown() && rhs.False() {
 					return cty.False
 				}
-				return cty.UnknownVal(cty.Bool)
+				return cty.UnknownVal(cty.Bool).RefineNotNull()
 			}
 			return cty.NilVal
 		},
diff --git a/hclsyntax/expression_test.go b/hclsyntax/expression_test.go
index 376073ad..d1dc35b9 100644
--- a/hclsyntax/expression_test.go
+++ b/hclsyntax/expression_test.go
@@ -1939,7 +1939,7 @@ EOT
 					"list":    cty.ListValEmpty(cty.Bool),
 				},
 			},
-			cty.UnknownVal(cty.Bool),
+			cty.UnknownVal(cty.Bool).RefineNotNull(),
 			0,
 		},
 		{
@@ -1968,7 +1968,7 @@ EOT
 					"list":    cty.ListValEmpty(cty.Bool),
 				},
 			},
-			cty.UnknownVal(cty.Bool),
+			cty.UnknownVal(cty.Bool).RefineNotNull(),
 			0,
 		},
 		{
@@ -3059,6 +3059,9 @@ func TestAllBoolExpressions(t *testing.T) {
 
 	for input, want := range inputs {
 		t.Run(input, func(t *testing.T) {
+			if !want.IsKnown() {
+				want = cty.UnknownVal(cty.Bool).RefineNotNull()
+			}
 			ctx := &hcl.EvalContext{
 				Variables: map[string]cty.Value{
 					"unknown": cty.UnknownVal(cty.DynamicPseudoType),
@@ -3077,6 +3080,10 @@ func TestAllBoolExpressions(t *testing.T) {
 				t.Fatalf("%q resulted in %#v, wanted %#v\n", input, got, want)
 			}
 			if !got.IsKnown() {
+				// this validates that the uknown refinements are correct too
+				if !got.RawEquals(want) {
+					t.Fatalf("wrong unknown, got:%#v, want:%#v\n", got, want)
+				}
 				// covered in known comparison
 				return
 			}