feat: group observer project files by round

Files on the observer project detail page are now grouped by round
(e.g., "Application Intake", "Semi-Finals Document Submission") instead
of shown in a flat list. Uses FileViewer's existing groupedFiles prop.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

src/components/observer/observer-project-detail.tsx

@@ -929,41 +929,66 @@ export function ObserverProjectDetail({ projectId }: { projectId: string }) {
               </CardTitle>
             </CardHeader>
             <CardContent>
-              {project.files && project.files.length > 0 ? (
+              {project.files && project.files.length > 0 ? (() => {
-                <FileViewer
+                // Group files by round
-                  projectId={projectId}
+                type FileItem = (typeof project.files)[number]
-                  files={project.files.map((f) => ({
+                const roundMap = new Map<string, { roundId: string | null; roundName: string; sortOrder: number; files: FileItem[] }>()
-                    id: f.id,
+                for (const f of project.files) {
-                    fileName: f.fileName,
+                  const key = (f as any).roundId ?? '__none__'
-                    fileType: f.fileType as
+                  if (!roundMap.has(key)) {
-                      | 'EXEC_SUMMARY'
+                    const round = (f as any).round as { id: string; name: string; sortOrder: number } | null
-                      | 'PRESENTATION'
+                    roundMap.set(key, {
-                      | 'VIDEO'
+                      roundId: round?.id ?? null,
-                      | 'OTHER'
+                      roundName: round?.name ?? 'Other Files',
-                      | 'BUSINESS_PLAN'
+                      sortOrder: round?.sortOrder ?? 999,
-                      | 'VIDEO_PITCH'
+                      files: [],
-                      | 'SUPPORTING_DOC',
+                    })
-                    mimeType: f.mimeType,
+                  }
-                    size: f.size,
+                  roundMap.get(key)!.files.push(f)
-                    bucket: f.bucket,
+                }
-                    objectKey: f.objectKey,
+                const groups = Array.from(roundMap.values()).sort((a, b) => a.sortOrder - b.sortOrder)
-                    pageCount: f.pageCount,
+
-                    textPreview: f.textPreview,
+                return (
-                    detectedLang: f.detectedLang,
+                  <FileViewer
-                    langConfidence: f.langConfidence,
+                    projectId={projectId}
-                    analyzedAt: f.analyzedAt ? String(f.analyzedAt) : null,
+                    groupedFiles={groups.map((g) => ({
-                    requirementId: f.requirementId,
+                      roundId: g.roundId,
-                    requirement: f.requirement
+                      roundName: g.roundName,
-                      ? {
+                      sortOrder: g.sortOrder,
-                          id: f.requirement.id,
+                      files: g.files.map((f) => ({
-                          name: f.requirement.name,
+                        id: f.id,
-                          description: f.requirement.description,
+                        fileName: f.fileName,
-                          isRequired: f.requirement.isRequired,
+                        fileType: f.fileType as
-                        }
+                          | 'EXEC_SUMMARY'
-                      : null,
+                          | '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,
+                      })),
+                    }))}
+                  />
+                )
+              })() : (
                 <div className="flex flex-col items-center justify-center py-8 text-center">
                   <FileText className="h-12 w-12 text-muted-foreground/50" />
                   <p className="mt-2 text-sm text-muted-foreground">

src/server/routers/analytics.ts

@@ -1378,9 +1378,12 @@ export const analyticsRouter = router({
                 id: true, fileName: true, fileType: true, mimeType: true, size: true,
                 bucket: true, objectKey: true, pageCount: true, textPreview: true,
                 detectedLang: true, langConfidence: true, analyzedAt: true,
+                roundId: true,
+                round: { select: { id: true, name: true, roundType: true, sortOrder: true } },
                 requirementId: true,
                 requirement: { select: { id: true, name: true, description: true, isRequired: true } },
               },
+              orderBy: [{ round: { sortOrder: 'asc' } }, { createdAt: 'asc' }],
             },
             teamMembers: {
               include: {
@@ -1526,6 +1529,7 @@ export const analyticsRouter = router({
       return {
         project: {
           ...projectRaw,
+          files: projectRaw.files,
           projectTags,
           teamMembers: teamMembersWithAvatars,
         },