diff --git a/frontend/src/views/CloudFolderView.vue b/frontend/src/views/CloudFolderView.vue
index 5594d66..dba3c15 100644
--- a/frontend/src/views/CloudFolderView.vue
+++ b/frontend/src/views/CloudFolderView.vue
@@ -443,6 +443,10 @@ function onFileOpen(file) {
  */
 async function onAnalyzeFile(file) {
   if (!file?.provider_item_id) return
+  // Re-analyze and Retry actions must bypass the already_current check (D-11).
+  const status = file.analysis_status
+  const needsForce = status === 'indexed' || status === 'already_current' ||
+    status === 'stale' || status === 'current' || status === 'failed' || status === 'partial'
   try {
     const estimate = await cloudStore.requestEstimate(connectionId.value, {
       scope: 'file',
@@ -453,6 +457,7 @@ async function onAnalyzeFile(file) {
       scope: 'file',
       provider_item_ids: [file.provider_item_id],
       recursive: false,
+      ...(needsForce ? { force: true } : {}),
     }
     // Show estimate modal — confirmed via onAnalysisConfirmed
     analysisEstimate.value = estimate