diff --git a/pkg/runner/run_context.go b/pkg/runner/run_context.go
index f0cd0c5..43ec4d5 100644
--- a/pkg/runner/run_context.go
+++ b/pkg/runner/run_context.go
@@ -314,7 +314,7 @@ func (rc *RunContext) EvalBool(expr string) (bool, error) {
 		joined := strings.Join(evaluatedParts, " ")
 		v, _, err := rc.ExprEval.Evaluate(fmt.Sprintf("Boolean(%s)", joined))
 		if err != nil {
-			return false, nil
+			return false, err
 		}
 		log.Debugf("expression '%s' evaluated to '%s'", expr, v)
 		return v == "true", nil
diff --git a/pkg/runner/run_context_test.go b/pkg/runner/run_context_test.go
index fd9de7e..01dab5e 100644
--- a/pkg/runner/run_context_test.go
+++ b/pkg/runner/run_context_test.go
@@ -2,13 +2,14 @@ package runner
 
 import (
 	"fmt"
-	"github.com/nektos/act/pkg/model"
-	a "github.com/stretchr/testify/assert"
 	"os"
 	"regexp"
 	"strings"
 	"testing"
 
+	"github.com/nektos/act/pkg/model"
+	a "github.com/stretchr/testify/assert"
+
 	"github.com/sirupsen/logrus/hooks/test"
 )
 
@@ -129,6 +130,8 @@ func TestRunContext_EvalBool(t *testing.T) {
 		// The special ACT flag
 		{in: "${{ env.ACT }}", out: true},
 		{in: "${{ !env.ACT }}", out: false},
+		// Invalid expressions should be reported
+		{in: "INVALID_EXPRESSION", wantErr: true},
 	}
 
 	updateTestIfWorkflow(t, tables, rc)