diff --git a/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/CodeModernizerSession.kt b/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/CodeModernizerSession.kt
index 973ac136ed5..50ec1a935d5 100644
--- a/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/CodeModernizerSession.kt
+++ b/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/CodeModernizerSession.kt
@@ -61,6 +61,7 @@ import java.net.ConnectException
 import java.net.SocketTimeoutException
 import java.net.UnknownHostException
 import java.nio.file.Path
+import java.time.Duration
 import java.time.Instant
 import java.util.Base64
 import java.util.concurrent.CancellationException
@@ -408,8 +409,10 @@ class CodeModernizerSession(
                 UnknownHostException::class,
                 SocketTimeoutException::class,
                 HttpRequests.HttpStatusException::class,
-                ConnectException::class
-            )
+                ConnectException::class,
+                IOException::class,
+            ),
+            maxDuration = Duration.ofMinutes(5)
         ) {
             clientAdaptor.uploadArtifactToS3(
                 createUploadUrlResponse.uploadUrl(),
diff --git a/plugins/amazonq/codetransform/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/codemodernizer/CodeWhispererCodeModernizerSessionTest.kt b/plugins/amazonq/codetransform/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/codemodernizer/CodeWhispererCodeModernizerSessionTest.kt
index bf0edb78620..4623edb2ff5 100644
--- a/plugins/amazonq/codetransform/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/codemodernizer/CodeWhispererCodeModernizerSessionTest.kt
+++ b/plugins/amazonq/codetransform/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/codemodernizer/CodeWhispererCodeModernizerSessionTest.kt
@@ -67,7 +67,6 @@ import software.aws.toolkits.jetbrains.utils.rules.HeavyJavaCodeInsightTestFixtu
 import software.aws.toolkits.jetbrains.utils.rules.addFileToModule
 import java.io.File
 import java.io.FileInputStream
-import java.io.IOException
 import java.net.ConnectException
 import java.util.Base64
 import java.util.zip.ZipFile
@@ -478,13 +477,13 @@ class CodeWhispererCodeModernizerSessionTest : CodeWhispererCodeModernizerTestBa
     }
 
     @Test
-    fun `CodeModernizer cannot upload payload due to unknown issue`() = runTest {
+    fun `CodeModernizer cannot upload payload due to unknown client-side issue`() = runTest {
         doReturn(ZipCreationResult.Succeeded(File("./tst-resources/codemodernizer/test.txt")))
             .whenever(testSessionContextSpy).createZipWithModuleFiles(any())
         doReturn(exampleCreateUploadUrlResponse).whenever(clientAdaptorSpy).createGumbyUploadUrl(any())
-        doAnswer { throw IOException("mock exception") }.whenever(clientAdaptorSpy).uploadArtifactToS3(any(), any(), any(), any(), any())
+        doAnswer { throw Exception("mock client-side exception") }.whenever(clientAdaptorSpy).uploadArtifactToS3(any(), any(), any(), any(), any())
         val result = testSessionSpy.createModernizationJob(MavenCopyCommandsResult.Success(File("./mock/path/")))
-        assertEquals(CodeModernizerStartJobResult.ZipUploadFailed(UploadFailureReason.OTHER("mock exception")), result)
+        assertEquals(CodeModernizerStartJobResult.ZipUploadFailed(UploadFailureReason.OTHER("mock client-side exception")), result)
         verify(testSessionStateSpy, times(1)).putJobHistory(any(), eq(TransformationStatus.FAILED), any(), any())
         assertEquals(testSessionStateSpy.currentJobStatus, TransformationStatus.FAILED)
     }