diff --git a/pkg/apis/pipeline/v1/when_types.go b/pkg/apis/pipeline/v1/when_types.go
index dfd6948ce73..66e7164a779 100644
--- a/pkg/apis/pipeline/v1/when_types.go
+++ b/pkg/apis/pipeline/v1/when_types.go
@@ -105,10 +105,7 @@ type WhenExpressions []WhenExpression
 // if the Task should be skipped.
 func (wes WhenExpressions) AllowsExecution(evaluatedCEL map[string]bool) bool {
 	for _, we := range wes {
-		if we.CEL != "" {
-			return evaluatedCEL[we.CEL]
-		}
-		if !we.isTrue() {
+		if !we.isTrue() || (we.CEL != "" && !evaluatedCEL[we.CEL]) {
 			return false
 		}
 	}
diff --git a/pkg/apis/pipeline/v1/when_types_test.go b/pkg/apis/pipeline/v1/when_types_test.go
index 22fe919d9fa..7d706a4b303 100644
--- a/pkg/apis/pipeline/v1/when_types_test.go
+++ b/pkg/apis/pipeline/v1/when_types_test.go
@@ -96,7 +96,36 @@ func TestAllowsExecution(t *testing.T) {
 		},
 		evaluatedCEL: map[string]bool{"'foo'!='foo'": false},
 		expected:     false,
-	}}
+	},
+		{
+			name: "multiple expressions - 1. CEL is true 2. In Op is false, expect false",
+			whenExpressions: WhenExpressions{
+				{
+					CEL: "'foo'=='foo'",
+				},
+				{
+					Input:    "foo",
+					Operator: selection.In,
+					Values:   []string{"bar"},
+				},
+			},
+			evaluatedCEL: map[string]bool{"'foo'=='foo'": true},
+			expected:     false,
+		},
+		{
+			name: "multiple expressions - 1. CEL is true 2. CEL is false, expect false",
+			whenExpressions: WhenExpressions{
+				{
+					CEL: "'foo'!='foo'",
+				},
+				{
+					CEL: "'xxx'!='xxx'",
+				},
+			},
+			evaluatedCEL: map[string]bool{"'foo'=='foo'": true, "'xxx'!='xxx'": false},
+			expected:     false,
+		},
+	}
 	for _, tc := range tests {
 		t.Run(tc.name, func(t *testing.T) {
 			got := tc.whenExpressions.AllowsExecution(tc.evaluatedCEL)
diff --git a/pkg/apis/pipeline/v1beta1/when_types.go b/pkg/apis/pipeline/v1beta1/when_types.go
index 8cea2f5ebf1..f792ec199c8 100644
--- a/pkg/apis/pipeline/v1beta1/when_types.go
+++ b/pkg/apis/pipeline/v1beta1/when_types.go
@@ -105,10 +105,7 @@ type WhenExpressions []WhenExpression
 // if the Task should be skipped.
 func (wes WhenExpressions) AllowsExecution(evaluatedCEL map[string]bool) bool {
 	for _, we := range wes {
-		if we.CEL != "" {
-			return evaluatedCEL[we.CEL]
-		}
-		if !we.isTrue() {
+		if !we.isTrue() || (we.CEL != "" && !evaluatedCEL[we.CEL]) {
 			return false
 		}
 	}
diff --git a/pkg/apis/pipeline/v1beta1/when_types_test.go b/pkg/apis/pipeline/v1beta1/when_types_test.go
index 914040d48d8..a7a75a2a635 100644
--- a/pkg/apis/pipeline/v1beta1/when_types_test.go
+++ b/pkg/apis/pipeline/v1beta1/when_types_test.go
@@ -96,7 +96,36 @@ func TestAllowsExecution(t *testing.T) {
 		},
 		evaluatedCEL: map[string]bool{"'foo'!='foo'": false},
 		expected:     false,
-	}}
+	},
+		{
+			name: "multiple expressions - 1. CEL is true 2. In Op is false, expect false",
+			whenExpressions: WhenExpressions{
+				{
+					CEL: "'foo'=='foo'",
+				},
+				{
+					Input:    "foo",
+					Operator: selection.In,
+					Values:   []string{"bar"},
+				},
+			},
+			evaluatedCEL: map[string]bool{"'foo'=='foo'": true},
+			expected:     false,
+		},
+		{
+			name: "multiple expressions - 1. CEL is true 2. CEL is false, expect false",
+			whenExpressions: WhenExpressions{
+				{
+					CEL: "'foo'!='foo'",
+				},
+				{
+					CEL: "'xxx'!='xxx'",
+				},
+			},
+			evaluatedCEL: map[string]bool{"'foo'=='foo'": true, "'xxx'!='xxx'": false},
+			expected:     false,
+		},
+	}
 	for _, tc := range tests {
 		t.Run(tc.name, func(t *testing.T) {
 			got := tc.whenExpressions.AllowsExecution(tc.evaluatedCEL)