diff --git a/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/constants/CodeTransformChatItems.kt b/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/constants/CodeTransformChatItems.kt
index bab116949c0..79eddf16a24 100644
--- a/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/constants/CodeTransformChatItems.kt
+++ b/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/constants/CodeTransformChatItems.kt
@@ -347,8 +347,8 @@ fun buildUserInputSQLConversionMetadataChatContent() = CodeTransformChatMessageC
     type = CodeTransformChatMessageType.FinalizedAnswer,
 )
 
-fun buildUserInputCustomDependencyVersionsChatContent() = CodeTransformChatMessageContent(
-    message = message("codemodernizer.chat.message.custom_dependency_upgrades_prompt"),
+fun buildUserInputCustomDependencyVersionsChatContent(message: String) = CodeTransformChatMessageContent(
+    message = message,
     buttons = listOf(
         confirmCustomDependencyVersionsButton,
         continueTransformationButton,
diff --git a/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/controller/CodeTransformChatController.kt b/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/controller/CodeTransformChatController.kt
index 3c9709f9fef..0bb237c9bda 100644
--- a/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/controller/CodeTransformChatController.kt
+++ b/plugins/amazonq/codetransform/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codemodernizer/controller/CodeTransformChatController.kt
@@ -465,7 +465,13 @@ class CodeTransformChatController(
     }
 
     private suspend fun promptForCustomYamlFile() {
-        codeTransformChatHelper.addNewMessage(buildUserInputCustomDependencyVersionsChatContent())
+        val sourceJdk = codeModernizerManager.codeTransformationSession?.sessionContext?.sourceJavaVersion?.name
+        val targetJdk = codeModernizerManager.codeTransformationSession?.sessionContext?.targetJavaVersion?.name
+        var message = message("codemodernizer.chat.message.custom_dependency_upgrades_prompt_library_upgrade")
+        if (sourceJdk != targetJdk) {
+            message = message("codemodernizer.chat.message.custom_dependency_upgrades_prompt_jdk_upgrade")
+        }
+        codeTransformChatHelper.addNewMessage(buildUserInputCustomDependencyVersionsChatContent(message))
         val sampleYAML = """
 name: "dependency-upgrade"
 description: "Custom dependency version management for Java migration from JDK 8/11/17 to JDK 17/21"
diff --git a/plugins/core/resources/resources/software/aws/toolkits/resources/MessagesBundle.properties b/plugins/core/resources/resources/software/aws/toolkits/resources/MessagesBundle.properties
index 45c4caea56b..7eaa9e89585 100644
--- a/plugins/core/resources/resources/software/aws/toolkits/resources/MessagesBundle.properties
+++ b/plugins/core/resources/resources/software/aws/toolkits/resources/MessagesBundle.properties
@@ -648,7 +648,8 @@ codemodernizer.chat.message.choose_objective=I can help you with the following t
 codemodernizer.chat.message.choose_objective_placeholder=Enter "language upgrade" or "sql conversion"
 codemodernizer.chat.message.custom_dependency_upgrades_continue=Ok, I will continue the transformation without additional dependency upgrade information.
 codemodernizer.chat.message.custom_dependency_upgrades_invalid=I wasn't able to parse the dependency upgrade file. Check that it's configured properly and try again. For an example of the required dependency upgrade file format, see the [documentation](https://docs.aws.amazon.com/amazonq/latest/qdeveloper-ug/code-transformation.html#dependency-upgrade-file).
-codemodernizer.chat.message.custom_dependency_upgrades_prompt=Would you like to provide a dependency upgrade file? You can specify first-party dependencies to upgrade in a YAML file, and I will upgrade them during the JDK upgrade (for example, Java 8 to 17). You can initiate a separate transformation (17 to 17 or 21 to 21) after the initial JDK upgrade to transform third-party dependencies.\n\nWithout a YAML file, I can perform a minimum JDK upgrade, and then you can initiate a separate transformation to upgrade all third-party dependencies as part of a maximum transformation. For an example dependency upgrade file, see the [documentation](https://docs.aws.amazon.com/amazonq/latest/qdeveloper-ug/code-transformation.html#dependency-upgrade-file).
+codemodernizer.chat.message.custom_dependency_upgrades_prompt_jdk_upgrade=Would you like to provide a dependency upgrade file? You can specify first party dependencies and their versions in a YAML file, and I will upgrade them during the JDK upgrade transformation. For an example dependency upgrade file, see the [documentation](https://docs.aws.amazon.com/amazonq/latest/qdeveloper-ug/code-transformation.html#dependency-upgrade-file).
+codemodernizer.chat.message.custom_dependency_upgrades_prompt_library_upgrade=Would you like to provide a dependency upgrade file? You can specify third party dependencies and their versions in a YAML file, and I will only upgrade these dependencies during the library upgrade transformation. For an example dependency upgrade file, see the [documentation](https://docs.aws.amazon.com/amazonq/latest/qdeveloper-ug/code-transformation.html#dependency-upgrade-file).
 codemodernizer.chat.message.custom_dependency_upgrades_valid=The dependency upgrade file looks good. I will use this information to upgrade the dependencies you specified.
 codemodernizer.chat.message.download_failed_client_instructions_expired=Your transformation is not available anymore. Your code and transformation summary are deleted 24 hours after the transformation completes. Please try starting the transformation again.
 codemodernizer.chat.message.download_failed_invalid_artifact=Sorry, I was unable to find your {0}. Artifacts are deleted after 24 hours. Please try starting the transformation again.