diff --git a/src/app/(admin)/admin/projects/[id]/page.tsx b/src/app/(admin)/admin/projects/[id]/page.tsx
index e376cd6..a02c368 100644
--- a/src/app/(admin)/admin/projects/[id]/page.tsx
+++ b/src/app/(admin)/admin/projects/[id]/page.tsx
@@ -816,33 +816,48 @@ function ProjectDetailContent({ projectId }: { projectId: string }) {
             />
           </div>
 
-          {/* All Files list */}
+          {/* All Files list — grouped by round */}
           {files && files.length > 0 && (
             <>
               <Separator />
               <FileViewer
                 projectId={projectId}
-                files={files.map((f) => ({
-                  id: f.id,
-                  fileName: f.fileName,
-                  fileType: f.fileType,
-                  mimeType: f.mimeType,
-                  size: f.size,
-                  bucket: f.bucket,
-                  objectKey: f.objectKey,
-                  pageCount: f.pageCount,
-                  textPreview: f.textPreview,
-                  detectedLang: f.detectedLang,
-                  langConfidence: f.langConfidence,
-                  analyzedAt: f.analyzedAt ? String(f.analyzedAt) : null,
-                  requirementId: f.requirementId,
-                  requirement: f.requirement ? {
-                    id: f.requirement.id,
-                    name: f.requirement.name,
-                    description: f.requirement.description,
-                    isRequired: f.requirement.isRequired,
-                  } : null,
-                }))}
+                groupedFiles={(() => {
+                  const groups = new Map<string, { roundId: string | null; roundName: string; sortOrder: number; files: typeof mappedFiles }>()
+                  const mappedFiles = files.map((f) => ({
+                    id: f.id,
+                    fileName: f.fileName,
+                    fileType: f.fileType as 'EXEC_SUMMARY' | 'PRESENTATION' | 'VIDEO' | 'OTHER' | 'BUSINESS_PLAN' | 'VIDEO_PITCH' | 'SUPPORTING_DOC',
+                    mimeType: f.mimeType,
+                    size: f.size,
+                    bucket: f.bucket,
+                    objectKey: f.objectKey,
+                    pageCount: f.pageCount,
+                    textPreview: f.textPreview,
+                    detectedLang: f.detectedLang,
+                    langConfidence: f.langConfidence,
+                    analyzedAt: f.analyzedAt ? String(f.analyzedAt) : null,
+                    requirementId: f.requirementId,
+                    requirement: f.requirement ? {
+                      id: f.requirement.id,
+                      name: f.requirement.name,
+                      description: f.requirement.description,
+                      isRequired: f.requirement.isRequired,
+                    } : null,
+                  }))
+                  for (const f of files) {
+                    const roundId = f.requirement?.roundId ?? null
+                    const roundName = f.requirement?.round?.name ?? 'General'
+                    const sortOrder = f.requirement?.round?.sortOrder ?? -1
+                    const key = roundId ?? '_general'
+                    if (!groups.has(key)) {
+                      groups.set(key, { roundId, roundName, sortOrder, files: [] })
+                    }
+                    const mapped = mappedFiles.find((m) => m.id === f.id)!
+                    groups.get(key)!.files.push(mapped)
+                  }
+                  return Array.from(groups.values())
+                })()}
               />
             </>
           )}
diff --git a/src/server/routers/file.ts b/src/server/routers/file.ts
index 3d39cfe..b36b202 100644
--- a/src/server/routers/file.ts
+++ b/src/server/routers/file.ts
@@ -358,7 +358,11 @@ export const fileRouter = router({
             },
           },
         },
-        orderBy: [{ fileType: 'asc' }, { createdAt: 'asc' }],
+        orderBy: [
+          { requirement: { round: { sortOrder: 'asc' } } },
+          { fileType: 'asc' },
+          { createdAt: 'asc' },
+        ],
       })
     }),