diff --git a/connector/connect/client/jvm/src/test/resources/TestHelloV2_2.12.jar b/connector/connect/client/jvm/src/test/resources/TestHelloV2_2.12.jar
new file mode 100644
index 000000000000..d89cf6543a20
Binary files /dev/null and b/connector/connect/client/jvm/src/test/resources/TestHelloV2_2.12.jar differ
diff --git a/connector/connect/client/jvm/src/test/resources/TestHelloV2_2.13.jar b/connector/connect/client/jvm/src/test/resources/TestHelloV2_2.13.jar
new file mode 100644
index 000000000000..6dee8fcd9c95
Binary files /dev/null and b/connector/connect/client/jvm/src/test/resources/TestHelloV2_2.13.jar differ
diff --git a/connector/connect/client/jvm/src/test/scala/org/apache/spark/sql/application/ReplE2ESuite.scala b/connector/connect/client/jvm/src/test/scala/org/apache/spark/sql/application/ReplE2ESuite.scala
index 61959234c879..720f66680ee1 100644
--- a/connector/connect/client/jvm/src/test/scala/org/apache/spark/sql/application/ReplE2ESuite.scala
+++ b/connector/connect/client/jvm/src/test/scala/org/apache/spark/sql/application/ReplE2ESuite.scala
@@ -17,12 +17,15 @@
 package org.apache.spark.sql.application
 
 import java.io.{PipedInputStream, PipedOutputStream}
+import java.nio.file.Paths
 import java.util.concurrent.{Executors, Semaphore, TimeUnit}
 
+import scala.util.Properties
+
 import org.apache.commons.io.output.ByteArrayOutputStream
 import org.scalatest.BeforeAndAfterEach
 
-import org.apache.spark.sql.connect.client.util.RemoteSparkSession
+import org.apache.spark.sql.connect.client.util.{IntegrationTestUtils, RemoteSparkSession}
 
 class ReplE2ESuite extends RemoteSparkSession with BeforeAndAfterEach {
 
@@ -35,6 +38,11 @@ class ReplE2ESuite extends RemoteSparkSession with BeforeAndAfterEach {
   private var ammoniteIn: PipedInputStream = _
   private val semaphore: Semaphore = new Semaphore(0)
 
+  private val scalaVersion = Properties.versionNumberString
+    .split("\\.")
+    .take(2)
+    .mkString(".")
+
   private def getCleanString(out: ByteArrayOutputStream): String = {
     // Remove ANSI colour codes
     // Regex taken from https://stackoverflow.com/a/25189932
@@ -96,7 +104,10 @@ class ReplE2ESuite extends RemoteSparkSession with BeforeAndAfterEach {
 
   def assertContains(message: String, output: String): Unit = {
     val isContain = output.contains(message)
-    assert(isContain, "Ammonite output did not contain '" + message + "':\n" + output)
+    assert(
+      isContain,
+      "Ammonite output did not contain '" + message + "':\n" + output +
+        s"\nError Output: ${getCleanString(errorStream)}")
   }
 
   test("Simple query") {
@@ -151,4 +162,33 @@ class ReplE2ESuite extends RemoteSparkSession with BeforeAndAfterEach {
     assertContains("Array[java.lang.Long] = Array(0L, 2L, 4L, 6L, 8L)", output)
   }
 
+  test("Client-side JAR") {
+    // scalastyle:off classforname line.size.limit
+    val sparkHome = IntegrationTestUtils.sparkHome
+    val testJar = Paths
+      .get(
+        s"$sparkHome/connector/connect/client/jvm/src/test/resources/TestHelloV2_$scalaVersion.jar")
+      .toFile
+
+    assert(testJar.exists(), "Missing TestHelloV2 jar!")
+    val input = s"""
+        |import java.nio.file.Paths
+        |def classLoadingTest(x: Int): Int = {
+        |  val classloader =
+        |    Option(Thread.currentThread().getContextClassLoader).getOrElse(getClass.getClassLoader)
+        |  val cls = Class.forName("com.example.Hello$$", true, classloader)
+        |  val module = cls.getField("MODULE$$").get(null)
+        |  cls.getMethod("test").invoke(module).asInstanceOf[Int]
+        |}
+        |val classLoaderUdf = udf(classLoadingTest _)
+        |
+        |val jarPath = Paths.get("${testJar.toString}").toUri
+        |spark.addArtifact(jarPath)
+        |
+        |spark.range(5).select(classLoaderUdf(col("id"))).as[Int].collect()
+      """.stripMargin
+    val output = runCommandsInShell(input)
+    assertContains("Array[Int] = Array(2, 2, 2, 2, 2)", output)
+    // scalastyle:on classforname line.size.limit
+  }
 }
diff --git a/connector/connect/server/src/main/scala/org/apache/spark/sql/connect/artifact/SparkConnectArtifactManager.scala b/connector/connect/server/src/main/scala/org/apache/spark/sql/connect/artifact/SparkConnectArtifactManager.scala
index 0a91c6b95502..9fd8e367e4aa 100644
--- a/connector/connect/server/src/main/scala/org/apache/spark/sql/connect/artifact/SparkConnectArtifactManager.scala
+++ b/connector/connect/server/src/main/scala/org/apache/spark/sql/connect/artifact/SparkConnectArtifactManager.scala
@@ -133,7 +133,7 @@ class SparkConnectArtifactManager(sessionHolder: SessionHolder) extends Logging
       Files.move(serverLocalStagingPath, target)
       if (remoteRelativePath.startsWith(s"jars${File.separator}")) {
         jarsList.add(target)
-        jarsURI.add(artifactURI + "/" + target.toString)
+        jarsURI.add(artifactURI + "/" + remoteRelativePath.toString)
       } else if (remoteRelativePath.startsWith(s"pyfiles${File.separator}")) {
         sessionHolder.session.sparkContext.addFile(target.toString)
         val stringRemotePath = remoteRelativePath.toString