diff --git a/cqf-fhir-cr/src/main/java/org/opencds/cqf/fhir/cr/questionnaireresponse/extract/ProcessDefinitionItem.java b/cqf-fhir-cr/src/main/java/org/opencds/cqf/fhir/cr/questionnaireresponse/extract/ProcessDefinitionItem.java
index bab9243e4..3e9012dac 100644
--- a/cqf-fhir-cr/src/main/java/org/opencds/cqf/fhir/cr/questionnaireresponse/extract/ProcessDefinitionItem.java
+++ b/cqf-fhir-cr/src/main/java/org/opencds/cqf/fhir/cr/questionnaireresponse/extract/ProcessDefinitionItem.java
@@ -230,21 +230,23 @@ private void processChild(
             IBaseBackboneElement childItem,
             String path) {
         var answers = request.resolvePathList(childItem, "answer", IBaseBackboneElement.class);
-        var answerValue = answers.isEmpty() ? null : request.resolvePath(answers.get(0), "value");
-        if (answerValue != null) {
-            // Check if answer type matches path types available and transform if necessary
-            var pathDefinition = (BaseRuntimeDeclaredChildDefinition) resourceDefinition.getChildByName(path);
-            if (pathDefinition instanceof RuntimeChildChoiceDefinition) {
-                var choices = ((RuntimeChildChoiceDefinition) pathDefinition).getChoices();
-                if (!choices.contains(answerValue.getClass())) {
+        var pathDefinition = (BaseRuntimeDeclaredChildDefinition) resourceDefinition.getChildByName(path);
+        List<Class<? extends IBase>> choices = pathDefinition instanceof RuntimeChildChoiceDefinition
+                ? ((RuntimeChildChoiceDefinition) pathDefinition).getChoices()
+                : new ArrayList<>();
+        answers.stream().forEach(answer -> {
+            var answerValue = request.resolvePath(answer, "value");
+            if (answerValue != null) {
+                // Check if answer type matches path types available and transform if necessary
+                if ((pathDefinition instanceof RuntimeChildChoiceDefinition
+                                && !choices.contains(answerValue.getClass()))
+                        || (pathDefinition instanceof RuntimeChildCompositeDatatypeDefinition
+                                && !pathDefinition.getField().getType().equals(answerValue.getClass()))) {
                     answerValue = transformValueToResource(request.getFhirVersion(), answerValue);
                 }
-            } else if (pathDefinition instanceof RuntimeChildCompositeDatatypeDefinition
-                    && !pathDefinition.getField().getType().equals(answerValue.getClass())) {
-                answerValue = transformValueToResource(request.getFhirVersion(), answerValue);
+                request.getModelResolver().setValue(resource, path, answerValue);
             }
-            request.getModelResolver().setValue(resource, path, answerValue);
-        }
+        });
     }
 
     private String getDefinition(
diff --git a/cqf-fhir-cr/src/test/java/org/opencds/cqf/fhir/cr/questionnaireresponse/extract/ProcessDefinitionItemTests.java b/cqf-fhir-cr/src/test/java/org/opencds/cqf/fhir/cr/questionnaireresponse/extract/ProcessDefinitionItemTests.java
index 637a1465d..cf8e13a45 100644
--- a/cqf-fhir-cr/src/test/java/org/opencds/cqf/fhir/cr/questionnaireresponse/extract/ProcessDefinitionItemTests.java
+++ b/cqf-fhir-cr/src/test/java/org/opencds/cqf/fhir/cr/questionnaireresponse/extract/ProcessDefinitionItemTests.java
@@ -1,6 +1,7 @@
 package org.opencds.cqf.fhir.cr.questionnaireresponse.extract;
 
 import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertInstanceOf;
 import static org.junit.jupiter.api.Assertions.assertThrows;
 import static org.mockito.ArgumentMatchers.any;
 import static org.mockito.ArgumentMatchers.eq;
@@ -21,11 +22,14 @@
 import org.hl7.fhir.r4.model.Condition;
 import org.hl7.fhir.r4.model.Expression;
 import org.hl7.fhir.r4.model.Extension;
+import org.hl7.fhir.r4.model.Patient;
 import org.hl7.fhir.r4.model.Questionnaire;
 import org.hl7.fhir.r4.model.Questionnaire.QuestionnaireItemComponent;
 import org.hl7.fhir.r4.model.QuestionnaireResponse;
+import org.hl7.fhir.r4.model.QuestionnaireResponse.QuestionnaireResponseItemAnswerComponent;
 import org.hl7.fhir.r4.model.QuestionnaireResponse.QuestionnaireResponseItemComponent;
 import org.hl7.fhir.r4.model.Reference;
+import org.hl7.fhir.r4.model.StringType;
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.extension.ExtendWith;
@@ -175,4 +179,30 @@ void testItemWithContextExtensionWithMultipleResources() {
         assertEquals(expectedCondition1, resources.get(0));
         assertEquals(expectedCondition2, resources.get(1));
     }
+
+    @Test
+    void testItemWithContextExtensionWithMultipleAnswers() {
+        var fhirVersion = FhirVersionEnum.R4;
+        var patientId = "patient1";
+        var item = new QuestionnaireItemComponent().setLinkId("1");
+        item.setDefinition("http://hl7.org/fhir/Patient#Patient.name.given");
+        var responseItem = new QuestionnaireResponseItemComponent().setLinkId("1");
+        responseItem.addAnswer(new QuestionnaireResponseItemAnswerComponent().setValue(new StringType("test1")));
+        responseItem.addAnswer(new QuestionnaireResponseItemAnswerComponent().setValue(new StringType("test2")));
+        var questionnaire = new Questionnaire().setItem(Arrays.asList(item));
+        var extension =
+                new Extension(Constants.SDC_QUESTIONNAIRE_ITEM_EXTRACTION_CONTEXT).setValue(new CodeType("Patient"));
+        questionnaire.addExtension(extension);
+        var response = new QuestionnaireResponse().setItem(Arrays.asList(responseItem));
+        var request = newExtractRequestForVersion(fhirVersion, libraryEngine, response, questionnaire);
+        var resources = new ArrayList<IBaseResource>();
+        var subjectId = Ids.newId(fhirVersion, "Patient", patientId);
+        var itemPair = new ItemPair(null, null);
+        fixture.processDefinitionItem(request, itemPair, resources, new Reference(subjectId));
+        assertEquals(1, resources.size());
+        assertInstanceOf(Patient.class, resources.get(0));
+        var patient = (Patient) resources.get(0);
+        assertEquals("test1", patient.getNameFirstRep().getGiven().get(0).asStringValue());
+        assertEquals("test2", patient.getNameFirstRep().getGiven().get(1).asStringValue());
+    }
 }