diff --git a/hclsyntax/expression_test.go b/hclsyntax/expression_test.go
index 6768ea86..39d261ca 100644
--- a/hclsyntax/expression_test.go
+++ b/hclsyntax/expression_test.go
@@ -2914,3 +2914,167 @@ func TestParseExpression_incompleteFunctionCall(t *testing.T) {
 		})
 	}
 }
+
+func TestAllBoolExpressions(t *testing.T) {
+	inputs := map[string]cty.Value{
+		// truth table for all boolean expressions
+		"true && true":       cty.True,
+		"true || true":       cty.True,
+		"true && false":      cty.False,
+		"true || false":      cty.True,
+		"true && unknown":    cty.DynamicVal,
+		"true || unknown":    cty.True,
+		"false && true":      cty.False,
+		"false || true":      cty.True,
+		"false && false":     cty.False,
+		"false || false":     cty.False,
+		"false && unknown":   cty.False,
+		"false || unknown":   cty.DynamicVal,
+		"unknown && true":    cty.DynamicVal,
+		"unknown || true":    cty.True,
+		"unknown && false":   cty.False,
+		"unknown || false":   cty.DynamicVal,
+		"unknown && unknown": cty.DynamicVal,
+		"unknown || unknown": cty.DynamicVal,
+
+		// truth table for all possible combinations 3 part boolean expressions
+		"true && true && true":          cty.True,
+		"true || true && true":          cty.True,
+		"true || true || true":          cty.True,
+		"true && true || true":          cty.True,
+		"true && true && false":         cty.False,
+		"true || true && false":         cty.True,
+		"true || true || false":         cty.True,
+		"true && true || false":         cty.True,
+		"true && true && unknown":       cty.DynamicVal,
+		"true || true && unknown":       cty.True,
+		"true || true || unknown":       cty.True,
+		"true && true || unknown":       cty.True,
+		"true && false && true":         cty.False,
+		"true || false && true":         cty.True,
+		"true || false || true":         cty.True,
+		"true && false || true":         cty.True,
+		"true && false && false":        cty.False,
+		"true || false && false":        cty.True,
+		"true || false || false":        cty.True,
+		"true && false || false":        cty.False,
+		"true && false && unknown":      cty.False,
+		"true || false && unknown":      cty.True,
+		"true || false || unknown":      cty.True,
+		"true && false || unknown":      cty.DynamicVal,
+		"true && unknown && true":       cty.DynamicVal,
+		"true || unknown && true":       cty.True,
+		"true || unknown || true":       cty.True,
+		"true && unknown || true":       cty.True,
+		"true && unknown && false":      cty.False,
+		"true || unknown && false":      cty.True,
+		"true || unknown || false":      cty.True,
+		"true && unknown || false":      cty.DynamicVal,
+		"true && unknown && unknown":    cty.DynamicVal,
+		"true || unknown && unknown":    cty.True,
+		"true || unknown || unknown":    cty.True,
+		"true && unknown || unknown":    cty.DynamicVal,
+		"false && true && true":         cty.False,
+		"false || true && true":         cty.True,
+		"false || true || true":         cty.True,
+		"false && true || true":         cty.True,
+		"false && true && false":        cty.False,
+		"false || true && false":        cty.False,
+		"false || true || false":        cty.True,
+		"false && true || false":        cty.False,
+		"false && true && unknown":      cty.False,
+		"false || true && unknown":      cty.DynamicVal,
+		"false || true || unknown":      cty.True,
+		"false && true || unknown":      cty.DynamicVal,
+		"false && false && true":        cty.False,
+		"false || false && true":        cty.False,
+		"false || false || true":        cty.True,
+		"false && false || true":        cty.True,
+		"false && false && false":       cty.False,
+		"false || false && false":       cty.False,
+		"false || false || false":       cty.False,
+		"false && false || false":       cty.False,
+		"false && false && unknown":     cty.False,
+		"false || false && unknown":     cty.False,
+		"false || false || unknown":     cty.DynamicVal,
+		"false && false || unknown":     cty.DynamicVal,
+		"false && unknown && true":      cty.False,
+		"false || unknown && true":      cty.DynamicVal,
+		"false || unknown || true":      cty.True,
+		"false && unknown || true":      cty.True,
+		"false && unknown && false":     cty.False,
+		"false || unknown && false":     cty.False,
+		"false || unknown || false":     cty.DynamicVal,
+		"false && unknown || false":     cty.False,
+		"false && unknown && unknown":   cty.False,
+		"false || unknown && unknown":   cty.DynamicVal,
+		"false || unknown || unknown":   cty.DynamicVal,
+		"false && unknown || unknown":   cty.DynamicVal,
+		"unknown && true && true":       cty.DynamicVal,
+		"unknown || true && true":       cty.True,
+		"unknown || true || true":       cty.True,
+		"unknown && true || true":       cty.True,
+		"unknown && true && false":      cty.False,
+		"unknown || true && false":      cty.DynamicVal,
+		"unknown || true || false":      cty.True,
+		"unknown && true || false":      cty.DynamicVal,
+		"unknown && true && unknown":    cty.DynamicVal,
+		"unknown || true && unknown":    cty.DynamicVal,
+		"unknown || true || unknown":    cty.True,
+		"unknown && true || unknown":    cty.DynamicVal,
+		"unknown && false && true":      cty.False,
+		"unknown || false && true":      cty.DynamicVal,
+		"unknown || false || true":      cty.True,
+		"unknown && false || true":      cty.True,
+		"unknown && false && false":     cty.False,
+		"unknown || false && false":     cty.DynamicVal,
+		"unknown || false || false":     cty.DynamicVal,
+		"unknown && false || false":     cty.False,
+		"unknown && false && unknown":   cty.False,
+		"unknown || false && unknown":   cty.DynamicVal,
+		"unknown || false || unknown":   cty.DynamicVal,
+		"unknown && false || unknown":   cty.DynamicVal,
+		"unknown && unknown && true":    cty.DynamicVal,
+		"unknown || unknown && true":    cty.DynamicVal,
+		"unknown || unknown || true":    cty.True,
+		"unknown && unknown || true":    cty.True,
+		"unknown && unknown && false":   cty.False,
+		"unknown || unknown && false":   cty.DynamicVal,
+		"unknown || unknown || false":   cty.DynamicVal,
+		"unknown && unknown || false":   cty.DynamicVal,
+		"unknown && unknown && unknown": cty.DynamicVal,
+		"unknown || unknown && unknown": cty.DynamicVal,
+		"unknown || unknown || unknown": cty.DynamicVal,
+		"unknown && unknown || unknown": cty.DynamicVal,
+	}
+
+	for input, want := range inputs {
+		t.Run(input, func(t *testing.T) {
+			ctx := &hcl.EvalContext{
+				Variables: map[string]cty.Value{
+					"unknown": cty.UnknownVal(cty.DynamicPseudoType),
+				},
+			}
+			expr, diags := ParseExpression([]byte(input), "", hcl.Pos{Line: 1, Column: 1, Byte: 0})
+			if diags.HasErrors() {
+				t.Fatal(diags.Error())
+			}
+			got, diags := expr.Value(ctx)
+			if diags.HasErrors() {
+				t.Fatal(diags.Error())
+			}
+
+			if got.IsKnown() != want.IsKnown() {
+				t.Fatalf("%q resulted in %#v, wanted %#v\n", input, got, want)
+			}
+			if !got.IsKnown() {
+				// covered in known comparison
+				return
+			}
+
+			if got.Equals(want).False() {
+				t.Fatalf("%q resulted in %#v, wanted %#v\n", input, got, want)
+			}
+		})
+	}
+}