diff --git a/flytepropeller/pkg/compiler/validators/typing.go b/flytepropeller/pkg/compiler/validators/typing.go
index 09268359dd..fc5cd368a6 100644
--- a/flytepropeller/pkg/compiler/validators/typing.go
+++ b/flytepropeller/pkg/compiler/validators/typing.go
@@ -356,5 +356,15 @@ func getTypeChecker(t *flyte.LiteralType) typeChecker {
 }
 
 func AreTypesCastable(upstreamType, downstreamType *flyte.LiteralType) bool {
-	return getTypeChecker(downstreamType).CastsFrom(upstreamType)
+	typeChecker := getTypeChecker(downstreamType)
+
+	// if upstream is a singular union we check if the downstream type is castable from the union variant
+	if upstreamType.GetUnionType() != nil && len(upstreamType.GetUnionType().GetVariants()) == 1 {
+		variants := upstreamType.GetUnionType().GetVariants()
+		if len(variants) == 1 && typeChecker.CastsFrom(variants[0]) {
+			return true
+		}
+	}
+
+	return typeChecker.CastsFrom(upstreamType)
 }
diff --git a/flytepropeller/pkg/compiler/validators/typing_test.go b/flytepropeller/pkg/compiler/validators/typing_test.go
index 8344339f09..146d314de2 100644
--- a/flytepropeller/pkg/compiler/validators/typing_test.go
+++ b/flytepropeller/pkg/compiler/validators/typing_test.go
@@ -326,6 +326,32 @@ func TestUnionCasting(t *testing.T) {
 		)
 		assert.False(t, castable, "Union types can only be cast to a union that contains a superset of variants")
 	})
+
+	t.Run("SingularUnionToUnderlyingType", func(t *testing.T) {
+		castable := AreTypesCastable(
+			&core.LiteralType{
+				Type: &core.LiteralType_UnionType{
+					UnionType: &core.UnionType{
+						Variants: []*core.LiteralType{
+							{
+								Type: &core.LiteralType_Simple{Simple: core.SimpleType_STRING},
+								Structure: &core.TypeStructure{
+									Tag: "string",
+								},
+							},
+						},
+					},
+				},
+			},
+			&core.LiteralType{
+				Type: &core.LiteralType_Simple{Simple: core.SimpleType_STRING},
+				Structure: &core.TypeStructure{
+					Tag: "string",
+				},
+			},
+		)
+		assert.True(t, castable, "Singular unions should be castable to their underlying type")
+	})
 }
 
 func TestCollectionCasting(t *testing.T) {