diff --git a/bvm/ballerina-runtime/src/main/java/io/ballerina/runtime/internal/TypeConverter.java b/bvm/ballerina-runtime/src/main/java/io/ballerina/runtime/internal/TypeConverter.java
index 6553c3628a52..eaa860e8e382 100644
--- a/bvm/ballerina-runtime/src/main/java/io/ballerina/runtime/internal/TypeConverter.java
+++ b/bvm/ballerina-runtime/src/main/java/io/ballerina/runtime/internal/TypeConverter.java
@@ -55,6 +55,7 @@
 
 import java.util.Collection;
 import java.util.HashMap;
+import java.util.HashSet;
 import java.util.Iterator;
 import java.util.List;
 import java.util.Map;
@@ -368,12 +369,12 @@ public static Type getConvertibleTypeInTargetUnionType(Object inputValue, BUnion
 
         for (Type memType : memberTypes) {
             if (TypeChecker.checkIsLikeType(inputValue, memType, false)) {
-                return getConvertibleType(inputValue, memType, varName, unresolvedValues, errors, false);
+                return getConvertibleType(inputValue, memType, varName, new HashSet<>(unresolvedValues), errors, false);
             }
         }
         for (Type memType : memberTypes) {
             Type convertibleTypeInUnion = getConvertibleType(inputValue, memType, varName,
-                    unresolvedValues, errors, allowNumericConversion);
+                    new HashSet<>(unresolvedValues), errors, allowNumericConversion);
             if (convertibleTypeInUnion != null) {
                 return convertibleTypeInUnion;
             }
@@ -391,7 +392,7 @@ private static Type getConvertibleStructuredTypeInUnion(Object inputValue, Strin
         for (Type memType : memberTypes) {
             initialErrorCount = errors.size();
             Type convertibleTypeInUnion = getConvertibleType(inputValue, memType, varName,
-                    unresolvedValues, errors, allowNumericConversion);
+                    new HashSet<>(unresolvedValues), errors, allowNumericConversion);
             currentErrorListSize = errors.size();
             if (convertibleTypeInUnion != null) {
                 errors.subList(initialErrorListSize - 1, currentErrorListSize).clear();
diff --git a/langlib/langlib-test/src/test/resources/test-src/valuelib_test.bal b/langlib/langlib-test/src/test/resources/test-src/valuelib_test.bal
index f7d4dc94ede4..5196d05deab3 100644
--- a/langlib/langlib-test/src/test/resources/test-src/valuelib_test.bal
+++ b/langlib/langlib-test/src/test/resources/test-src/valuelib_test.bal
@@ -2351,6 +2351,89 @@ function testCloneWithTypeWithAmbiguousUnion() {
     <string>checkpanic err.detail()["message"]);
 }
 
+public type CodingExtension record {|
+    *Element;
+
+    uri url;
+    Coding valueCoding;
+|};
+
+public type Coding record {|
+    *Element;
+
+    string id?;
+    Extension[] extension?;
+    uri system?;
+    string 'version?;
+    code code?;
+    string display?;
+    boolean userSelected?;
+|};
+
+public type code string;
+
+public type uri string;
+
+public type ElementReadOnlyCyclic record {|
+    string id?;
+    Extension[] extension?;
+    ((ElementReadOnlyCyclic & readonly)|())...;
+|};
+
+public type Element record {|
+    string id?;
+    Extension[] extension?;
+    Element...;
+|};
+
+public type ExtensionExtension record {|
+    *Element;
+
+    uri url;
+    Extension[] extension?;
+|};
+
+public type CodeableConceptExtension record {|
+    *Element;
+
+    uri url;
+    CodeableConcept valueCodeableConcept;
+|};
+
+public type CodeableConcept record {|
+    *Element;
+
+    string id?;
+    Extension[] extension?;
+    Coding[] coding?;
+    string text?;
+|};
+
+public type ExtensionExtension2 record {|
+    *ElementReadOnlyCyclic;
+
+    uri url;
+    Extension[] extension?;
+|};
+
+public type CodeableConceptExtension2 record {|
+    *ElementReadOnlyCyclic;
+
+    uri url;
+    CodeableConcept valueCodeableConcept;
+|};
+
+public type CodingExtension2 record {|
+    *ElementReadOnlyCyclic;
+
+    uri url;
+    Coding valueCoding;
+|};
+
+public type Extension CodeableConceptExtension|ExtensionExtension|CodingExtension;
+
+public type Extension2 CodeableConceptExtension2|ExtensionExtension2|CodingExtension2;
+
 function testCloneWithTypeToUnion() {
     int|float|[string, string] unionVar = 2;
     float|decimal|[string, int]|error tupleValue = unionVar.cloneWithType(UnionTypedesc);
@@ -2359,6 +2442,31 @@ function testCloneWithTypeToUnion() {
     assertFalse(tupleValue is decimal);
     assertFalse(tupleValue is [string, int]);
     assertFalse(tupleValue is error);
+
+    json extCoding = {
+        "valueCoding": {
+            "system": "http://loinc.org",
+            "code": "LA29518-0",
+            "display": "he/him/his/himself"
+        },
+        "url": "http://open.epic.com/FHIR/StructureDefinition/extension/calculated-pronouns-to-use-for-text"
+    };
+
+    Extension ext = checkpanic extCoding.cloneWithType();
+    assertEquality(ext, <Extension>{
+        "url":
+    "http://open.epic.com/FHIR/StructureDefinition/extension/calculated-pronouns-to-use-for-text",
+        "valueCoding": {"system": "http://loinc.org", "code": "LA29518-0", "display": "he/him/his/himself"}
+    });
+    assertEquality((typeof ext).toString(), "typedesc CodingExtension");
+
+    Extension2 ext2 = checkpanic extCoding.cloneWithType();
+    assertEquality(ext2, <Extension2>{
+        "url":
+    "http://open.epic.com/FHIR/StructureDefinition/extension/calculated-pronouns-to-use-for-text",
+        "valueCoding": {"system": "http://loinc.org", "code": "LA29518-0", "display": "he/him/his/himself"}
+    });
+    assertEquality((typeof ext2).toString(), "typedesc CodingExtension2");
 }
 
 type UnionTypedesc typedesc<float|decimal|[string, int]>;