diff --git a/Yattee/Data/Bookmark.swift b/Yattee/Data/Bookmark.swift
index b032d970..9c8c65a0 100644
--- a/Yattee/Data/Bookmark.swift
+++ b/Yattee/Data/Bookmark.swift
@@ -217,7 +217,7 @@ final class Bookmark {
             publishedText: publishedText,
             viewCount: viewCount,
             likeCount: nil,
-            thumbnails: thumbnailURL.map { [Thumbnail(url: $0, width: nil, height: nil)] } ?? [],
+            thumbnails: Thumbnail.fallbackChain(for: thumbnailURL),
             isLive: isLive,
             isUpcoming: false,
             scheduledStartTime: nil
diff --git a/Yattee/Data/LocalPlaylist.swift b/Yattee/Data/LocalPlaylist.swift
index 3cb73119..e7864c93 100644
--- a/Yattee/Data/LocalPlaylist.swift
+++ b/Yattee/Data/LocalPlaylist.swift
@@ -75,10 +75,16 @@ final class LocalPlaylist {
     }
 
     /// The first video's thumbnail URL for display.
+    ///
+    /// Rewritten to the always-available `hqdefault` variant because the stored
+    /// URL is the best advertised quality (often `maxresdefault`), which 404s
+    /// for many older videos and would leave the cover blank.
     var thumbnailURL: URL? {
-        (items ?? []).sorted { $0.sortOrder < $1.sortOrder }
-            .first?
-            .thumbnailURL
+        Thumbnail.reliableURL(
+            for: (items ?? []).sorted { $0.sortOrder < $1.sortOrder }
+                .first?
+                .thumbnailURL
+        )
     }
 
     /// Sorted items by order.
@@ -249,7 +255,7 @@ extension LocalPlaylistItem {
             publishedText: nil,
             viewCount: nil,
             likeCount: nil,
-            thumbnails: thumbnailURL.map { [Thumbnail(url: $0, quality: .medium)] } ?? [],
+            thumbnails: Thumbnail.fallbackChain(for: thumbnailURL),
             isLive: isLive,
             isUpcoming: false,
             scheduledStartTime: nil
diff --git a/Yattee/Data/WatchEntry.swift b/Yattee/Data/WatchEntry.swift
index 2bd2e05b..f34eceeb 100644
--- a/Yattee/Data/WatchEntry.swift
+++ b/Yattee/Data/WatchEntry.swift
@@ -241,7 +241,7 @@ extension WatchEntry {
             publishedText: nil,
             viewCount: nil,
             likeCount: nil,
-            thumbnails: thumbnailURL.map { [Thumbnail(url: $0, quality: .medium)] } ?? [],
+            thumbnails: Thumbnail.fallbackChain(for: thumbnailURL),
             isLive: isLive,
             isUpcoming: false,
             scheduledStartTime: nil
diff --git a/Yattee/Models/Video.swift b/Yattee/Models/Video.swift
index e379e4bc..28718d29 100644
--- a/Yattee/Models/Video.swift
+++ b/Yattee/Models/Video.swift
@@ -311,6 +311,55 @@ struct Thumbnail: Codable, Hashable, Sendable {
         self.width = width
         self.height = height
     }
+
+    /// Expands a single stored YouTube-style thumbnail URL (`/vi/<id>/<variant>.jpg`)
+    /// into a best-first fallback chain. Persistence models (playlists, watch history,
+    /// bookmarks) store only the best advertised URL — usually `maxresdefault.jpg`,
+    /// which doesn't exist for many older videos and 404s. Reconstructing the
+    /// lower-quality variants lets thumbnail views fall back the same way they do
+    /// for live API results. Non-matching URLs get a single-entry chain.
+    /// Rewrites a YouTube-style thumbnail URL (`/vi/<id>/<variant>.jpg`) to the
+    /// `hqdefault.jpg` variant, which exists for effectively every video (unlike
+    /// `maxresdefault`/`sddefault`, which 404 for many older uploads). Use where a
+    /// single URL is displayed without fallback, e.g. playlist covers. Non-matching
+    /// URLs are returned unchanged.
+    static func reliableURL(for url: URL?) -> URL? {
+        guard let url else { return nil }
+        let variants = ["maxresdefault.jpg", "sddefault.jpg", "hqdefault.jpg", "mqdefault.jpg", "default.jpg"]
+        let path = url.path
+        guard path.range(of: #"/vi/[^/]+/"#, options: .regularExpression) != nil,
+              let match = variants.first(where: { path.hasSuffix($0) }),
+              var components = URLComponents(url: url, resolvingAgainstBaseURL: false) else {
+            return url
+        }
+        components.path = String(path.dropLast(match.count)) + "hqdefault.jpg"
+        return components.url ?? url
+    }
+
+    static func fallbackChain(for url: URL?) -> [Thumbnail] {
+        guard let url else { return [] }
+        let variants: [(suffix: String, quality: Quality)] = [
+            ("maxresdefault.jpg", .maxres),
+            ("sddefault.jpg", .standard),
+            ("hqdefault.jpg", .high),
+            ("mqdefault.jpg", .medium),
+            ("default.jpg", .default),
+        ]
+        let path = url.path
+        guard path.range(of: #"/vi/[^/]+/"#, options: .regularExpression) != nil,
+              let current = variants.first(where: { path.hasSuffix($0.suffix) }),
+              let components = URLComponents(url: url, resolvingAgainstBaseURL: false) else {
+            return [Thumbnail(url: url, quality: .medium)]
+        }
+        let basePath = String(path.dropLast(current.suffix.count))
+        return variants.compactMap { variant in
+            guard variant.quality <= current.quality else { return nil }
+            var variantComponents = components
+            variantComponents.path = basePath + variant.suffix
+            guard let variantURL = variantComponents.url else { return nil }
+            return Thumbnail(url: variantURL, quality: variant.quality)
+        }
+    }
 }
 
 // MARK: - Preview Support
diff --git a/Yattee/Services/API/PipedAPI.swift b/Yattee/Services/API/PipedAPI.swift
index 06489b48..ef77f4b3 100644
--- a/Yattee/Services/API/PipedAPI.swift
+++ b/Yattee/Services/API/PipedAPI.swift
@@ -590,7 +590,7 @@ private struct PipedStreamResponse: Decodable, Sendable {
         let thumbnails: [Thumbnail] = {
             if !resolvedVideoId.isEmpty,
                let url = URL(string: "https://i.ytimg.com/vi/\(resolvedVideoId)/maxresdefault.jpg") {
-                return [Thumbnail(url: url, quality: .maxres)]
+                return Thumbnail.fallbackChain(for: url)
             }
             // Fallback to proxy URL if video ID not available
             if let proxyURL = thumbnailUrl.flatMap({ URL(string: $0) }) {
diff --git a/Yattee/Services/Downloads/Download.swift b/Yattee/Services/Downloads/Download.swift
index da0efcc3..7e2ffd7a 100644
--- a/Yattee/Services/Downloads/Download.swift
+++ b/Yattee/Services/Downloads/Download.swift
@@ -336,7 +336,7 @@ struct Download: Identifiable, Codable, Sendable, Equatable {
             publishedText: publishedText,
             viewCount: viewCount,
             likeCount: likeCount,
-            thumbnails: resolvedThumbnailURL.map { [Thumbnail(url: $0, quality: .medium)] } ?? [],
+            thumbnails: Thumbnail.fallbackChain(for: resolvedThumbnailURL),
             isLive: false,
             isUpcoming: false,
             scheduledStartTime: nil
diff --git a/Yattee/Services/Downloads/DownloadManager.swift b/Yattee/Services/Downloads/DownloadManager.swift
index fc406c7f..20eefc37 100644
--- a/Yattee/Services/Downloads/DownloadManager.swift
+++ b/Yattee/Services/Downloads/DownloadManager.swift
@@ -960,7 +960,7 @@ final class DownloadManager: NSObject {
             publishedText: download.publishedText,
             viewCount: download.viewCount,
             likeCount: download.likeCount,
-            thumbnails: download.thumbnailURL.map { [Thumbnail(url: $0, quality: .medium)] } ?? [],
+            thumbnails: Thumbnail.fallbackChain(for: download.thumbnailURL),
             isLive: false,
             isUpcoming: false,
             scheduledStartTime: nil