diff --git a/packages/amazonq/.changes/next-release/Bug Fix-316fb610-0ea9-40d1-bdb7-d371a6be4a4e.json b/packages/amazonq/.changes/next-release/Bug Fix-316fb610-0ea9-40d1-bdb7-d371a6be4a4e.json
new file mode 100644
index 00000000000..1a9e5c32e6d
--- /dev/null
+++ b/packages/amazonq/.changes/next-release/Bug Fix-316fb610-0ea9-40d1-bdb7-d371a6be4a4e.json	
@@ -0,0 +1,4 @@
+{
+	"type": "Bug Fix",
+	"description": "Let Enter invoke auto completion more consistently"
+}
diff --git a/packages/amazonq/src/app/inline/completion.ts b/packages/amazonq/src/app/inline/completion.ts
index f6e080453f0..9020deac824 100644
--- a/packages/amazonq/src/app/inline/completion.ts
+++ b/packages/amazonq/src/app/inline/completion.ts
@@ -241,6 +241,12 @@ export class AmazonQInlineCompletionItemProvider implements InlineCompletionItem
             return []
         }
 
+        const isAutoTrigger = context.triggerKind === InlineCompletionTriggerKind.Automatic
+        if (isAutoTrigger && !CodeSuggestionsState.instance.isSuggestionsEnabled()) {
+            // return early when suggestions are disabled with auto trigger
+            return []
+        }
+
         // yield event loop to let the document listen catch updates
         await sleep(1)
         // prevent user deletion invoking auto trigger
@@ -254,12 +260,6 @@ export class AmazonQInlineCompletionItemProvider implements InlineCompletionItem
         try {
             const t0 = performance.now()
             vsCodeState.isRecommendationsActive = true
-            const isAutoTrigger = context.triggerKind === InlineCompletionTriggerKind.Automatic
-            if (isAutoTrigger && !CodeSuggestionsState.instance.isSuggestionsEnabled()) {
-                // return early when suggestions are disabled with auto trigger
-                return []
-            }
-
             // handling previous session
             const prevSession = this.sessionManager.getActiveSession()
             const prevSessionId = prevSession?.sessionId
diff --git a/packages/amazonq/src/app/inline/documentEventListener.ts b/packages/amazonq/src/app/inline/documentEventListener.ts
index 4e60b595ce2..36f65dc7331 100644
--- a/packages/amazonq/src/app/inline/documentEventListener.ts
+++ b/packages/amazonq/src/app/inline/documentEventListener.ts
@@ -21,6 +21,11 @@ export class DocumentEventListener {
                     this.lastDocumentChangeEventMap.clear()
                 }
                 this.lastDocumentChangeEventMap.set(e.document.uri.fsPath, { event: e, timestamp: performance.now() })
+                // The VS Code provideInlineCompletionCallback may not trigger when Enter is pressed, especially in Python files
+                // manually make this trigger. In case of duplicate, the provideInlineCompletionCallback is already debounced
+                if (this.isEnter(e) && vscode.window.activeTextEditor) {
+                    void vscode.commands.executeCommand('editor.action.inlineSuggest.trigger')
+                }
             }
         })
     }
@@ -47,4 +52,18 @@ export class DocumentEventListener {
             this.documentChangeListener.dispose()
         }
     }
+
+    private isEnter(e: vscode.TextDocumentChangeEvent): boolean {
+        if (e.contentChanges.length !== 1) {
+            return false
+        }
+        const str = e.contentChanges[0].text
+        if (str.length === 0) {
+            return false
+        }
+        return (
+            (str.startsWith('\r\n') && str.substring(2).trim() === '') ||
+            (str[0] === '\n' && str.substring(1).trim() === '')
+        )
+    }
 }