diff --git a/.changes/next-release/bugfix-8abe8650-ac4a-40ea-9243-071fd3104029.json b/.changes/next-release/bugfix-8abe8650-ac4a-40ea-9243-071fd3104029.json
new file mode 100644
index 00000000000..ea1937bbd8c
--- /dev/null
+++ b/.changes/next-release/bugfix-8abe8650-ac4a-40ea-9243-071fd3104029.json
@@ -0,0 +1,4 @@
+{
+  "type" : "bugfix",
+  "description" : "Amazon Q /dev: Fix additional retry attempt required on entering a prompt"
+}
\ No newline at end of file
diff --git a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/controller/FeatureDevControllerExtensions.kt b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/controller/FeatureDevControllerExtensions.kt
index ccd52ed5fd0..949e1ca42ec 100644
--- a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/controller/FeatureDevControllerExtensions.kt
+++ b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/controller/FeatureDevControllerExtensions.kt
@@ -50,7 +50,7 @@ suspend fun FeatureDevController.onCodeGeneration(
             message = message("amazonqFeatureDev.chat_message.requesting_changes"),
             messageType = FeatureDevMessageType.AnswerStream,
         )
-        val state = session.sessionState
+        var state = session.sessionState
 
         var remainingIterations: Int? = state.codeGenerationRemainingIterationCount
         var totalIterations: Int? = state.codeGenerationTotalIterationCount
@@ -64,6 +64,8 @@ suspend fun FeatureDevController.onCodeGeneration(
 
         session.send(message) // Trigger code generation
 
+        state = session.sessionState
+
         var filePaths: List<NewFileZipInfo> = emptyList()
         var deletedFiles: List<DeletedFileInfo> = emptyList()
         var references: List<CodeReferenceGenerated> = emptyList()