diff --git a/src/lib/ae_events/ae_events__event_file.ts b/src/lib/ae_events/ae_events__event_file.ts
index 3fc0ed15..d2b9e1be 100644
--- a/src/lib/ae_events/ae_events__event_file.ts
+++ b/src/lib/ae_events/ae_events__event_file.ts
@@ -372,27 +372,59 @@ export async function delete_ae_obj_id__event_file({
 }: {
     api_cfg: any;
     event_file_id: string;
-    // Providing hosted_file_id enables full cleanup: removes the hosted_file_link,
-    // then deletes the hosted_file record and physical file if no other links remain.
-    // Must be done BEFORE deleting the event_file record so the backend can still
-    // resolve the link_to_id via Redis.
+    // Providing hosted_file_id enables full cleanup of the physical file and
+    // hosted_file record. The /links fetch is done first because it calls
+    // get_id_random() on each linked object, which populates Redis. Without
+    // this pre-fetch, redis_lookup_id_random('event_file', id) raises 404
+    // in the delete handler — the cleanup is silently skipped.
     hosted_file_id?: string;
     params?: key_val;
     try_cache?: boolean;
     log_lvl?: number;
 }) {
     if (hosted_file_id) {
-        await api.delete_hosted_file({
-            api_cfg,
-            hosted_file_id,
-            link_to_type: 'event_file',
-            link_to_id: event_file_id,
-            rm_orphan: true,
-            params: { method: 'delete' },
-            log_lvl
-        });
+        // Step 1: Fetch links — populates Redis for all linked object IDs.
+        let file_links: { link_to_type: string; link_to_id_random: string | null }[] = [];
+        try {
+            const links_result = await api.get_object({
+                api_cfg,
+                endpoint: `/v3/action/hosted_file/${hosted_file_id}/links`,
+                log_lvl: 0
+            });
+            file_links = links_result?.data ?? links_result ?? [];
+        } catch (e) {
+            if (log_lvl) console.warn('[delete_event_file] /links fetch failed:', e);
+        }
+
+        // Step 2: Remove each link. rm_orphan=true on the last one triggers
+        // physical file + hosted_file record cleanup if nothing else uses it.
+        if (file_links.length > 0) {
+            for (let i = 0; i < file_links.length; i++) {
+                const lnk = file_links[i];
+                const is_last = i === file_links.length - 1;
+                await api.delete_hosted_file({
+                    api_cfg,
+                    hosted_file_id,
+                    link_to_type: lnk.link_to_type,
+                    link_to_id: lnk.link_to_id_random ?? undefined,
+                    rm_orphan: is_last,
+                    params: { method: 'delete' },
+                    log_lvl
+                });
+            }
+        } else {
+            // No links recorded — attempt direct orphan cleanup.
+            await api.delete_hosted_file({
+                api_cfg,
+                hosted_file_id,
+                rm_orphan: true,
+                params: { method: 'delete' },
+                log_lvl
+            });
+        }
     }
 
+    // Step 3: Delete the event_file record after the hosted_file cleanup.
     const result = await api.delete_ae_obj({
         api_cfg,
         obj_type: 'event_file',
diff --git a/src/routes/core/files/+page.svelte b/src/routes/core/files/+page.svelte
index b40c7c1e..101bfcb7 100644
--- a/src/routes/core/files/+page.svelte
+++ b/src/routes/core/files/+page.svelte
@@ -18,6 +18,7 @@ import {
     RefreshCw,
     Search,
     Trash2,
+    Unlink,
     X
 } from '@lucide/svelte';
 
@@ -336,6 +337,53 @@ function fmt_date(val: string | Date | null | undefined) {
 }
 
 let total_size = $derived(results.reduce((sum, f) => sum + (f.size ?? 0), 0));
+
+// ── Orphan check ──────────────────────────────────────────────────────────────
+// A file is a confirmed orphan once links_map has been populated for it AND the
+// links array is empty. links_map is a SvelteMap so this derived stays reactive.
+let orphan_checking = $state(false);
+let orphan_filter = $state(false);
+
+let orphan_ids = $derived(
+    new Set(
+        results
+            .filter((f) => links_map.has(f.hosted_file_id) && (links_map.get(f.hosted_file_id)?.length ?? 1) === 0)
+            .map((f) => f.hosted_file_id)
+    )
+);
+
+let displayed_results = $derived(
+    orphan_filter ? results.filter((f) => orphan_ids.has(f.hosted_file_id)) : results
+);
+
+async function check_all_for_orphans() {
+    orphan_checking = true;
+    orphan_filter = false;
+    // Fetch links for all visible results in parallel; skip already-cached entries.
+    await Promise.all(
+        results.map(async (file) => {
+            const id = file.hosted_file_id;
+            if (links_map.has(id)) return;
+            links_loading.set(id, true);
+            try {
+                const result = await api.get_object({
+                    api_cfg: $ae_api,
+                    endpoint: `/v3/action/hosted_file/${id}/links`,
+                    log_lvl: 0
+                });
+                links_map.set(id, result?.data ?? result ?? []);
+                // Also resolve nav URLs for any links found
+                await Promise.all((result?.data ?? result ?? []).map((lnk: any) => resolve_link_url(lnk.link_to_type, lnk.link_to_id_random)));
+            } catch {
+                links_map.set(id, []);
+            } finally {
+                links_loading.delete(id);
+            }
+        })
+    );
+    orphan_filter = true;
+    orphan_checking = false;
+}
 </script>
 
 <div class="space-y-6">
@@ -460,15 +508,45 @@ let total_size = $derived(results.reduce((sum, f) => sum + (f.size ?? 0), 0));
     {#if results.length > 0}
         <div class="card preset-tonal-surface border-surface-500/10 border shadow-xl">
 
-            <div class="border-surface-500/20 flex items-center justify-between border-b px-4 py-2">
+            <div class="border-surface-500/20 flex flex-wrap items-center justify-between gap-2 border-b px-4 py-2">
                 <span class="text-xs font-bold opacity-60">
-                    {results.length} file{results.length !== 1 ? 's' : ''}
+                    {#if orphan_filter}
+                        <span class="text-warning-600 dark:text-warning-400">
+                            {orphan_ids.size} orphan{orphan_ids.size !== 1 ? 's' : ''} of {results.length}
+                        </span>
+                    {:else}
+                        {results.length} file{results.length !== 1 ? 's' : ''}
+                    {/if}
                     {#if results.length === page_limit}
-                        <span class="opacity-50"> (may be more — increase per-page or paginate)</span>
+                        <span class="opacity-50"> (may be more)</span>
                     {/if}
                     · <span class="tabular-nums">{fmt_size(total_size)}</span> total
                 </span>
-                <div class="flex items-center gap-2">
+                <div class="flex flex-wrap items-center gap-2">
+                    <!-- Orphan check -->
+                    {#if orphan_filter}
+                        <button
+                            type="button"
+                            class="btn btn-sm preset-tonal-warning text-xs"
+                            onclick={() => { orphan_filter = false; }}
+                            title="Show all files">
+                            <Unlink size={12} class="mr-1" />
+                            {orphan_ids.size} orphan{orphan_ids.size !== 1 ? 's' : ''} — Show All
+                        </button>
+                    {:else}
+                        <button
+                            type="button"
+                            class="btn btn-sm preset-tonal-surface text-xs"
+                            onclick={check_all_for_orphans}
+                            disabled={orphan_checking}
+                            title="Check all visible files for missing links (orphan detection)">
+                            {#if orphan_checking}
+                                <LoaderCircle size={12} class="mr-1 animate-spin" /> Checking…
+                            {:else}
+                                <Unlink size={12} class="mr-1" /> Check Orphans
+                            {/if}
+                        </button>
+                    {/if}
                     {#if page_offset > 0}
                         <button
                             type="button"
@@ -544,7 +622,7 @@ let total_size = $derived(results.reduce((sum, f) => sum + (f.size ?? 0), 0));
                         </tr>
                     </thead>
                     <tbody>
-                        {#each results as file (file.hosted_file_id)}
+                        {#each displayed_results as file (file.hosted_file_id)}
                             <tr
                                 class="border-surface-500/10 hover:bg-surface-500/5 border-b transition-colors duration-200"
                                 class:opacity-50={!file.enable}>
@@ -560,6 +638,11 @@ let total_size = $derived(results.reduce((sum, f) => sum + (f.size ?? 0), 0));
                                         {#if file.hide}
                                             <span class="badge preset-tonal-surface ml-1 text-[9px]">hidden</span>
                                         {/if}
+                                        {#if orphan_ids.has(file.hosted_file_id)}
+                                            <span class="badge preset-tonal-warning ml-1 text-[9px]" title="No links found — safe to delete">
+                                                <Unlink size={9} class="mr-0.5" /> orphan
+                                            </span>
+                                        {/if}
                                     </div>
                                 </td>
                                 <td class="px-3 py-2 tabular-nums">{fmt_size(file.size)}</td>