diff --git a/app/features/ytdlp/utils.py b/app/features/ytdlp/utils.py
index 745f98fc..50e1ab2f 100644
--- a/app/features/ytdlp/utils.py
+++ b/app/features/ytdlp/utils.py
@@ -37,9 +37,7 @@ class _DATA:
         {
             "quiet": "-q, --quiet",
             "no_warnings": "--no-warnings",
-            "skip_download": "--skip-download",
             "forceprint": "-O, --print",
-            "simulate": "--simulate",
             "noprogress": "--no-progress",
             "wait_for_video": "--wait-for-video",
             "progress_delta": " --progress-delta",
diff --git a/app/library/ItemDTO.py b/app/library/ItemDTO.py
index f4ef3d85..91c5b211 100644
--- a/app/library/ItemDTO.py
+++ b/app/library/ItemDTO.py
@@ -381,6 +381,8 @@ class ItemDTO:
     """ The archive ID of the item. """
     sidecar: dict = field(default_factory=dict)
     """ Sidecar data associated with the item. """
+    download_skipped: bool = False
+    """ True when yt-dlp intentionally skips the primary media download. """
 
     # yt-dlp injected fields.
     tmpfilename: str | None = None
diff --git a/app/library/downloads/core.py b/app/library/downloads/core.py
index 7dcf3907..ef18e746 100644
--- a/app/library/downloads/core.py
+++ b/app/library/downloads/core.py
@@ -92,9 +92,11 @@ class Download:
         download using yt-dlp.
         """
         cookie_file: Path | None = None
+        params: dict[str, Any] = {}
+        download_skipped = False
 
         try:
-            params: dict = (
+            params = (
                 self.info.get_ytdlp_opts()
                 .add(
                     config={
@@ -116,6 +118,7 @@ class Download:
                 )
                 .get_all()
             )
+            download_skipped = bool(params.get("skip_download") or params.get("simulate"))
 
             params.update(
                 {
@@ -212,7 +215,7 @@ class Download:
 
                 signal.signal(signal.SIGUSR1, mark_cancelled)
 
-            self.status_queue.put({"id": self.id, "status": "downloading"})
+            self.status_queue.put({"id": self.id, "status": "downloading", "download_skipped": download_skipped})
 
             if isinstance(self.info_dict, dict) and len(self.info_dict) > 1:
                 self.logger.debug(f"Downloading '{self.info.url}' using pre-info.")
@@ -232,14 +235,35 @@ class Download:
                 self.logger.debug(f"Downloading using url: {self.info.url}")
                 ret = cls.download(url_list=[self.info.url])
 
-            self.status_queue.put({"id": self.id, "status": "finished" if 0 == ret else "error"})
+            self.status_queue.put(
+                {
+                    "id": self.id,
+                    "status": "finished" if 0 == ret else "error",
+                    "download_skipped": download_skipped,
+                }
+            )
         except yt_dlp.utils.ExistingVideoReached as exc:
             self.logger.error(exc)
-            self.status_queue.put({"id": self.id, "status": "skip", "msg": "Item has already been downloaded."})
+            self.status_queue.put(
+                {
+                    "id": self.id,
+                    "status": "skip",
+                    "msg": "Item has already been downloaded.",
+                    "download_skipped": download_skipped,
+                }
+            )
         except Exception as exc:
             self.logger.exception(exc)
             self.logger.error(exc)
-            self.status_queue.put({"id": self.id, "status": "error", "msg": str(exc), "error": str(exc)})
+            self.status_queue.put(
+                {
+                    "id": self.id,
+                    "status": "error",
+                    "msg": str(exc),
+                    "error": str(exc),
+                    "download_skipped": download_skipped,
+                }
+            )
         finally:
             self.status_queue.put(Terminator())
             if cookie_file and cookie_file.exists():
diff --git a/app/library/downloads/status_tracker.py b/app/library/downloads/status_tracker.py
index edd248d8..d7a10748 100644
--- a/app/library/downloads/status_tracker.py
+++ b/app/library/downloads/status_tracker.py
@@ -128,6 +128,8 @@ class StatusTracker:
         self.tmpfilename = status.get("tmpfilename")
 
         self.info.status = status.get("status", self.info.status)
+        if "download_skipped" in status:
+            self.info.download_skipped = bool(status.get("download_skipped"))
         self.info.msg = status.get("msg")
         self.info.postprocessor = status.get("postprocessor", None)
 
diff --git a/app/tests/test_download.py b/app/tests/test_download.py
index f32a7d8a..2faf5193 100644
--- a/app/tests/test_download.py
+++ b/app/tests/test_download.py
@@ -272,6 +272,58 @@ class TestDownloadStale:
 
 
 class TestDownloadFlow:
+    def test_download_pushes_download_skipped_flag(self, monkeypatch: pytest.MonkeyPatch) -> None:
+        class Cfg:
+            debug = False
+            ytdlp_debug = False
+            max_workers = 1
+            temp_keep = False
+            temp_disabled = True
+            download_info_expires = 3600
+
+            @staticmethod
+            def get_instance():
+                return Cfg
+
+        monkeypatch.setattr("app.library.downloads.core.Config", Cfg)
+
+        download = Download(
+            info=make_item(),
+            info_dict={"id": "test-id", "url": "http://u", "formats": [{"format_id": "18"}]},
+        )
+        download.status_queue = cast(Any, DummyQueue())
+        download._hook_handlers = Mock(
+            progress_hook=Mock(),
+            postprocessor_hook=Mock(),
+            post_hook=Mock(),
+        )
+        download.info.get_ytdlp_opts = Mock(
+            return_value=Mock(
+                add=Mock(
+                    return_value=Mock(
+                        get_all=Mock(return_value={"skip_download": True}),
+                    )
+                )
+            )
+        )
+
+        class FakeYTDLP:
+            def __init__(self, params):
+                self.params = params
+                self._download_retcode = 0
+                self._interrupted = False
+
+            def process_ie_result(self, ie_result, download):
+                return ie_result, download
+
+        monkeypatch.setattr("app.library.downloads.core.YTDLP", FakeYTDLP)
+
+        download._download()
+
+        queue = cast(DummyQueue, download.status_queue)
+        assert queue.items[0]["download_skipped"] is True
+        assert queue.items[1]["download_skipped"] is True
+
     @pytest.mark.asyncio
     async def test_download_flow_inline_process(self, monkeypatch: pytest.MonkeyPatch, tmp_path: Path) -> None:
         class Cfg:
@@ -724,6 +776,14 @@ class TestStatusTracker:
         await st.process_status_update(status)
         assert st.info.status == "downloading", "Should update info status"
 
+    @pytest.mark.asyncio
+    async def test_process_status_update_sets_download_skipped(self, mock_config: dict) -> None:
+        st = StatusTracker(**mock_config)
+        status = {"id": "test-id", "status": "downloading", "download_skipped": True}
+
+        await st.process_status_update(status)
+        assert st.info.download_skipped is True, "Should update download_skipped from status queue"
+
     @pytest.mark.asyncio
     async def test_process_status_update_sets_tmpfilename(self, mock_config: dict) -> None:
         st = StatusTracker(**mock_config)
diff --git a/app/tests/test_itemdto.py b/app/tests/test_itemdto.py
index 72a27a9a..0358d57d 100644
--- a/app/tests/test_itemdto.py
+++ b/app/tests/test_itemdto.py
@@ -110,6 +110,23 @@ class TestItemDTO:
         assert dto.is_archivable is True
         assert dto.is_archived is True
 
+    @patch("app.library.ItemDTO.get_archive_id")
+    @patch("app.library.ItemDTO.YTDLPOpts")
+    @patch("app.library.ItemDTO.archive_read")
+    def test_post_init_does_not_infer_download_skipped_flag(self, mock_read, mock_opts, mock_get_id):
+        mock_get_id.return_value = {"archive_id": "arch", "id": "arch", "ie_key": "YT"}
+        mock_opts.get_instance.return_value.preset.return_value = mock_opts.get_instance.return_value
+        mock_opts.get_instance.return_value.add_cli.return_value = mock_opts.get_instance.return_value
+        mock_opts.get_instance.return_value.get_all.return_value = {
+            "download_archive": "/tmp/a.txt",
+            "skip_download": True,
+        }
+        mock_read.return_value = ["arch"]
+
+        dto = ItemDTO(id="vid", title="t", url="u", folder="f")
+
+        assert dto.download_skipped is False
+
     @patch("app.library.ItemDTO.archive_read")
     def test_serialize_triggers_archive_status_when_finished(self, mock_read):
         # Given a finished item with archive info
@@ -125,12 +142,32 @@ class TestItemDTO:
         for key in ItemDTO.removed_fields():
             assert key not in data
 
+    @patch("app.library.ItemDTO.YTDLPOpts")
+    def test_serialize_does_not_recompute_download_skipped(self, mock_opts):
+        mock_opts.get_instance.return_value.preset.return_value = mock_opts.get_instance.return_value
+        mock_opts.get_instance.return_value.add_cli.return_value = mock_opts.get_instance.return_value
+        mock_opts.get_instance.return_value.get_all.return_value = {}
+
+        dto = ItemDTO(id="vid", title="t", url="u", folder="f", download_skipped=True)
+
+        mock_opts.get_instance.reset_mock()
+
+        data = dto.serialize()
+
+        assert data["download_skipped"] is True
+        mock_opts.get_instance.assert_not_called()
+
     @patch("app.library.ItemDTO.YTDLPOpts")
     def test_get_ytdlp_opts_uses_preset_and_cli(self, mock_opts):
         mock_opts.get_instance.return_value.preset.return_value = mock_opts.get_instance.return_value
         mock_opts.get_instance.return_value.add_cli.return_value = mock_opts.get_instance.return_value
 
         dto = ItemDTO(id="id", title="t", url="u", folder="f", preset="p", cli="--x")
+
+        mock_opts.get_instance.reset_mock()
+        mock_opts.get_instance.return_value.preset.reset_mock()
+        mock_opts.get_instance.return_value.add_cli.reset_mock()
+
         opts = dto.get_ytdlp_opts()
 
         mock_opts.get_instance.assert_called_once()
diff --git a/app/tests/test_sqlite_store.py b/app/tests/test_sqlite_store.py
index 3a52c3d8..263182dd 100644
--- a/app/tests/test_sqlite_store.py
+++ b/app/tests/test_sqlite_store.py
@@ -17,13 +17,15 @@ async def make_store() -> SqliteStore:
     return store
 
 
-def make_item(idx: int, *, status: str = "finished") -> ItemDTO:
+def make_item(idx: int, *, status: str = "finished", cli: str = "", download_skipped: bool = False) -> ItemDTO:
     return ItemDTO(
         id=f"vid{idx}",
         title=f"Video {idx}",
         url=f"https://example.com/{idx}",
         folder="/downloads",
         status=status,
+        cli=cli,
+        download_skipped=download_skipped,
     )
 
 
@@ -90,6 +92,22 @@ async def test_enqueue_upsert_and_fetch_saved():
     await store.close()
 
 
+@pytest.mark.asyncio
+async def test_enqueue_upsert_persists_download_skipped_flag():
+    store = await make_store()
+    item = make_item(2, download_skipped=True)
+
+    await store.enqueue_upsert("history", item)
+    await store.flush()
+
+    saved = await store.fetch_saved("history")
+    assert len(saved) == 1
+    _, loaded = saved[0]
+    assert item.download_skipped is True
+    assert loaded.download_skipped is True
+    await store.close()
+
+
 @pytest.mark.asyncio
 async def test_delete_and_bulk_delete():
     store = await make_store()
diff --git a/ui/app/components/History.vue b/ui/app/components/History.vue
index 8c3c96dd..0bd3dd7c 100644
--- a/ui/app/components/History.vue
+++ b/ui/app/components/History.vue
@@ -214,7 +214,7 @@
               <td class="w-44 px-3 py-3 align-top whitespace-nowrap">
                 <div class="flex items-center justify-end gap-1">
                   <UButton
-                    v-if="!item.filename"
+                    v-if="showRetryAction(item)"
                     color="warning"
                     variant="outline"
                     size="xs"
@@ -442,7 +442,7 @@
 
           <div class="flex flex-wrap gap-2 *:min-w-32 *:flex-1">
             <UButton
-              v-if="!item.filename"
+              v-if="showRetryAction(item)"
               color="warning"
               variant="outline"
               icon="i-lucide-rotate-cw"
@@ -616,7 +616,7 @@ import { useStorage, useIntersectionObserver } from '@vueuse/core';
 import { useDialog } from '~/composables/useDialog';
 import type { StoreItem } from '~/types/store';
 import { useConfirm } from '~/composables/useConfirm';
-import { deepIncludes, getPath, getImage } from '~/utils';
+import { deepIncludes, getPath, getImage, isDownloadSkipped } from '~/utils';
 import type { item_request } from '~/types/item';
 
 const emitter = defineEmits<{
@@ -816,6 +816,8 @@ const getListImage = (item: StoreItem): string =>
 
 const getGridImage = (item: StoreItem): string => getImage(config.app.download_path, item) || '';
 
+const showRetryAction = (item: StoreItem): boolean => !item.filename && !isDownloadSkipped(item);
+
 const historyCardClass = (item: StoreItem): string => {
   if (item.status === 'error') {
     return 'border-error';
@@ -1038,6 +1040,9 @@ const clearIncomplete = async () => {
 
 const setIcon = (item: StoreItem) => {
   if ('finished' === item.status) {
+    if (isDownloadSkipped(item)) {
+      return 'i-lucide-ban';
+    }
     if (!item.filename) {
       return 'i-lucide-triangle-alert';
     }
@@ -1063,6 +1068,9 @@ const setIcon = (item: StoreItem) => {
 
 const setIconColor = (item: StoreItem) => {
   if ('finished' === item.status) {
+    if (isDownloadSkipped(item)) {
+      return 'text-info';
+    }
     if (!item.filename) {
       return 'text-warning';
     }
@@ -1084,6 +1092,9 @@ const setIconColor = (item: StoreItem) => {
 
 const setStatus = (item: StoreItem) => {
   if ('finished' === item.status) {
+    if (isDownloadSkipped(item)) {
+      return 'Download skipped';
+    }
     if (item.extras?.is_premiere) {
       return 'Premiered';
     }
diff --git a/ui/app/components/Simple.vue b/ui/app/components/Simple.vue
index aae4dc1e..b2401907 100644
--- a/ui/app/components/Simple.vue
+++ b/ui/app/components/Simple.vue
@@ -445,6 +445,7 @@ import {
   ag,
   encodePath,
   formatTime,
+  isDownloadSkipped,
   makeDownload,
   request,
   stripPath,
@@ -812,6 +813,10 @@ const getStatusLabel = (item: StoreItem): string => {
     return 'Queued';
   }
 
+  if (isDownloadSkipped(item)) {
+    return 'Download skipped';
+  }
+
   if (item.status === 'error' && item.filename) {
     return 'Partial Error';
   }
@@ -824,6 +829,10 @@ const getStatusColor = (item: StoreItem): 'neutral' | 'info' | 'success' | 'erro
     return 'neutral';
   }
 
+  if (isDownloadSkipped(item)) {
+    return 'info';
+  }
+
   if (item.status === 'error' && item.filename) {
     return 'warning';
   }
diff --git a/ui/app/types/store.d.ts b/ui/app/types/store.d.ts
index 268758fd..ad2f7f18 100644
--- a/ui/app/types/store.d.ts
+++ b/ui/app/types/store.d.ts
@@ -70,6 +70,8 @@ type StoreItem = {
     subtitle?: Array<sideCarSubtitle>;
     image?: Array<SideCar>;
   };
+  /** If the primary media download was intentionally skipped */
+  download_skipped?: boolean;
   /** Extras for the item */
   extras: {
     /** Which channel the item belongs to */
diff --git a/ui/app/utils/index.ts b/ui/app/utils/index.ts
index 548c017c..08b6a4e3 100644
--- a/ui/app/utils/index.ts
+++ b/ui/app/utils/index.ts
@@ -793,6 +793,10 @@ const shortPath = (path: string, prefix: string = '...'): string => {
   return `${prefix}/${parts.at(-1)}${hasTrailingSlash ? '/' : ''}`;
 };
 
+const isDownloadSkipped = (
+  item: Pick<StoreItem, 'status' | 'download_skipped'> | null | undefined,
+): boolean => Boolean(item && item.status === 'finished' && item.download_skipped);
+
 /**
  * Recursively test if a value (including nested objects/arrays) contains a query string.
  * - Plain queries match keys or values (case-insensitive).
@@ -1028,6 +1032,7 @@ export {
   enableOpacity,
   stripPath,
   shortPath,
+  isDownloadSkipped,
   deepIncludes,
   getPath,
   getImage,
diff --git a/ui/tests/utils/index.test.ts b/ui/tests/utils/index.test.ts
index c32ab448..3cd931fe 100644
--- a/ui/tests/utils/index.test.ts
+++ b/ui/tests/utils/index.test.ts
@@ -388,6 +388,16 @@ describe('data conversion helpers', () => {
     const url = utils.makeDownload({}, { filename: 'playlist' }, 'm3u8');
     expect(url).toBe('/base-path/api/player/m3u8/video/playlist.m3u8');
   });
+
+  it('isDownloadSkipped detects finished skipped-download items', () => {
+    expect(utils.isDownloadSkipped({ status: 'finished', download_skipped: true } as any)).toBe(true);
+  });
+
+  it('isDownloadSkipped ignores unfinished or unflagged items', () => {
+    expect(utils.isDownloadSkipped({ status: 'finished', download_skipped: false } as any)).toBe(false);
+    expect(utils.isDownloadSkipped({ status: 'downloading', download_skipped: true } as any)).toBe(false);
+    expect(utils.isDownloadSkipped(undefined as any)).toBe(false);
+  });
 });
 
 describe('dom and browser helpers', () => {