diff --git a/hapi-fhir-jpaserver-base/src/main/java/ca/uhn/fhir/jpa/patch/FhirPatch.java b/hapi-fhir-jpaserver-base/src/main/java/ca/uhn/fhir/jpa/patch/FhirPatch.java
index 3e66965339c..15de32b78f4 100644
--- a/hapi-fhir-jpaserver-base/src/main/java/ca/uhn/fhir/jpa/patch/FhirPatch.java
+++ b/hapi-fhir-jpaserver-base/src/main/java/ca/uhn/fhir/jpa/patch/FhirPatch.java
@@ -369,14 +369,7 @@ public class FhirPatch {
 		// Find newly inserted items
 		while (targetIndex < targetValues.size()) {
 			String path = theTargetPath + "." + elementName;
-
-
-			IBase operation = ParametersUtil.addParameterToParameters(myContext, theDiff, "operation");
-			ParametersUtil.addPartCode(myContext, operation, "type", "insert");
-			ParametersUtil.addPartString(myContext, operation, "path", path);
-			ParametersUtil.addPartInteger(myContext, operation, "index", targetIndex);
-			ParametersUtil.addPart(myContext, operation, "value", targetValues.get(targetIndex));
-
+			addInsertItems(theDiff, targetValues, targetIndex, path, theChildDef);
 			targetIndex++;
 		}
 
@@ -393,6 +386,36 @@ public class FhirPatch {
 		theSourceEncodePath.popPath();
 	}
 
+	private void addInsertItems(IBaseParameters theDiff, List<? extends IBase> theTargetValues, int theTargetIndex, String thePath, BaseRuntimeChildDefinition theChildDefinition) {
+		IBase operation = ParametersUtil.addParameterToParameters(myContext, theDiff, "operation");
+		ParametersUtil.addPartCode(myContext, operation, "type", "insert");
+		ParametersUtil.addPartString(myContext, operation, "path", thePath);
+		ParametersUtil.addPartInteger(myContext, operation, "index", theTargetIndex);
+
+		IBase value = theTargetValues.get(theTargetIndex);
+		BaseRuntimeElementDefinition<?> valueDef = myContext.getElementDefinition(value.getClass());
+
+		/*
+		 * If the value is a Resource or a datatype, we can put it into the part.value and that will cover
+		 * all of its children. If it's an infrastructure element though, such as Patient.contact we can't
+		 * just put it into part.value because it isn't an actual type. So we have to put all of its
+		 * childen in instead.
+		 */
+		if (valueDef.isStandardType()) {
+			ParametersUtil.addPart(myContext, operation, "value", value);
+		} else {
+			for (BaseRuntimeChildDefinition nextChild : valueDef.getChildren()) {
+				List<IBase> childValues = nextChild.getAccessor().getValues(value);
+				for (int index = 0; index < childValues.size(); index++) {
+					boolean childRepeatable = theChildDefinition.getMax() != 1;
+					String elementName = nextChild.getChildNameByDatatype(childValues.get(index).getClass());
+					String targetPath = thePath + (childRepeatable ? "[" + index + "]" : "") + "." + elementName;
+					addInsertItems(theDiff, childValues, index, targetPath, nextChild);
+				}
+			}
+		}
+	}
+
 	private void addValueToDiff(IBase theOperationPart, IBase theOldValue, IBase theNewValue) {
 
 		if (myIncludePreviousValueInDiff) {
diff --git a/hapi-fhir-jpaserver-base/src/test/java/ca/uhn/fhir/jpa/patch/FhirPatchApplyR4Test.java b/hapi-fhir-jpaserver-base/src/test/java/ca/uhn/fhir/jpa/patch/FhirPatchApplyR4Test.java
index 35b9e95f977..d48e1ee9f84 100644
--- a/hapi-fhir-jpaserver-base/src/test/java/ca/uhn/fhir/jpa/patch/FhirPatchApplyR4Test.java
+++ b/hapi-fhir-jpaserver-base/src/test/java/ca/uhn/fhir/jpa/patch/FhirPatchApplyR4Test.java
@@ -12,6 +12,7 @@ import org.hl7.fhir.r4.model.Patient;
 import org.hl7.fhir.r4.model.StringType;
 import org.junit.Test;
 
+import javax.annotation.Nullable;
 import java.util.stream.Collectors;
 
 import static org.junit.Assert.assertEquals;
@@ -170,9 +171,13 @@ public class FhirPatchApplyR4Test {
 		return ((IPrimitiveType) part.getValue()).getValueAsString();
 	}
 
+	@Nullable
 	public static <T extends IBase> T extractPartValue(Parameters theDiff, int theIndex, String theParameterName, String thePartName, Class<T> theExpectedType) {
 		Parameters.ParametersParameterComponent component = theDiff.getParameter().stream().filter(t -> t.getName().equals(theParameterName)).collect(Collectors.toList()).get(theIndex);
-		Parameters.ParametersParameterComponent part = component.getPart().stream().filter(t -> t.getName().equals(thePartName)).findFirst().orElseThrow(() -> new IllegalArgumentException());
+		Parameters.ParametersParameterComponent part = component.getPart().stream().filter(t -> t.getName().equals(thePartName)).findFirst().orElse(null);
+		if (part == null) {
+			return null;
+		}
 
 		if (IBaseResource.class.isAssignableFrom(theExpectedType)) {
 			return (T) part.getResource();
diff --git a/hapi-fhir-jpaserver-base/src/test/java/ca/uhn/fhir/jpa/patch/FhirPatchDiffR4Test.java b/hapi-fhir-jpaserver-base/src/test/java/ca/uhn/fhir/jpa/patch/FhirPatchDiffR4Test.java
index 11b643942d5..6d3f80de0d5 100644
--- a/hapi-fhir-jpaserver-base/src/test/java/ca/uhn/fhir/jpa/patch/FhirPatchDiffR4Test.java
+++ b/hapi-fhir-jpaserver-base/src/test/java/ca/uhn/fhir/jpa/patch/FhirPatchDiffR4Test.java
@@ -1,9 +1,11 @@
 package ca.uhn.fhir.jpa.patch;
 
 import ca.uhn.fhir.context.FhirContext;
+import org.hl7.fhir.instance.model.api.IBase;
 import org.hl7.fhir.r4.model.BooleanType;
 import org.hl7.fhir.r4.model.DateTimeType;
 import org.hl7.fhir.r4.model.Extension;
+import org.hl7.fhir.r4.model.HumanName;
 import org.hl7.fhir.r4.model.Identifier;
 import org.hl7.fhir.r4.model.Parameters;
 import org.hl7.fhir.r4.model.Patient;
@@ -319,6 +321,30 @@ public class FhirPatchDiffR4Test {
 		validateDiffProducesSameResults(oldValue, newValue, svc, diff);
 	}
 
+	@Test
+	public void testInsertContact() {
+		Patient oldValue = new Patient();
+
+		Patient newValue = new Patient();
+		newValue.addContact().getName().setFamily("My Family");
+
+		FhirPatch svc = new FhirPatch(ourCtx);
+		Parameters diff = (Parameters) svc.diff(oldValue, newValue);
+
+		ourLog.info(ourCtx.newJsonParser().setPrettyPrint(true).encodeResourceToString(diff));
+
+		assertEquals(2, diff.getParameter().size());
+		assertEquals("insert", extractPartValuePrimitive(diff, 0, "operation", "type"));
+		assertEquals("Patient.contact", extractPartValuePrimitive(diff, 0, "operation", "path"));
+		assertEquals(null, extractPartValue(diff, 0, "operation", "value", IBase.class));
+		assertEquals("insert", extractPartValuePrimitive(diff, 1, "operation", "type"));
+		assertEquals("Patient.contact[0].name", extractPartValuePrimitive(diff, 1, "operation", "path"));
+		assertEquals("My Family", extractPartValue(diff, 1, "operation", "value", HumanName.class).getFamily());
+
+		validateDiffProducesSameResults(oldValue, newValue, svc, diff);
+	}
+
+
 	@Test
 	public void testIgnoreElementComposite_Resource() {
 		Patient oldValue = new Patient();