diff --git a/TheIntroDB/Configuration/PluginConfiguration.cs b/TheIntroDB/Configuration/PluginConfiguration.cs
index e182a92..5e055d6 100644
--- a/TheIntroDB/Configuration/PluginConfiguration.cs
+++ b/TheIntroDB/Configuration/PluginConfiguration.cs
@@ -80,5 +80,10 @@ public PluginConfiguration()
         /// instead of the main Emby log.
         /// </summary>
         public bool EnableFileLogging { get; set; }
+
+        /// <summary>
+        /// Gets or sets a value indicating whether to automatically fetch segments for newly added items and on playback start.
+        /// </summary>
+        public bool EnableOnDemandFetch { get; set; } = true;
     }
 }
diff --git a/TheIntroDB/Configuration/configPage.html b/TheIntroDB/Configuration/configPage.html
index b122798..9164322 100644
--- a/TheIntroDB/Configuration/configPage.html
+++ b/TheIntroDB/Configuration/configPage.html
@@ -70,6 +70,14 @@ <h2 class="sectionTitle">TheIntroDB</h2>
                 <div class="fieldDescription">When enabled, items that already have segments are skipped to avoid refetching.</div>
             </div>
 
+            <div class="checkboxContainer checkboxContainer-withDescription">
+                <label class="emby-checkbox-label">
+                    <input id="EnableOnDemandFetch" name="EnableOnDemandFetch" type="checkbox" is="emby-checkbox" />
+                    <span>Automatically fetch segments on item addition</span>
+                </label>
+                <div class="fieldDescription">When enabled, segments will be fetched for newly added items, so long as no segments exist yet.</div>
+            </div>
+
             <div class="checkboxContainer checkboxContainer-withDescription">
                 <label class="emby-checkbox-label">
                     <input id="EnableAnonymousUsageReporting" name="EnableAnonymousUsageReporting" type="checkbox" is="emby-checkbox" />
diff --git a/TheIntroDB/Configuration/configPage.js b/TheIntroDB/Configuration/configPage.js
index 0232f99..0155705 100644
--- a/TheIntroDB/Configuration/configPage.js
+++ b/TheIntroDB/Configuration/configPage.js
@@ -955,6 +955,7 @@ define(["emby-input", "emby-button", "emby-checkbox"], function () {
                                 page.querySelector('#EnableCredits').checked = config.EnableCredits !== false;
                                 page.querySelector('#EnablePreview').checked = config.EnablePreview !== false;
                                 page.querySelector('#IgnoreMediaWithExistingSegments').checked = config.IgnoreMediaWithExistingSegments !== false;
+                                page.querySelector('#EnableOnDemandFetch').checked = config.EnableOnDemandFetch !== false;
                                 page.querySelector('#EnableAnonymousUsageReporting').checked = config.EnableAnonymousUsageReporting !== false;
                                 page.querySelector('#EnableFileLogging').checked = config.EnableFileLogging === true;
                                 if (apiKeyInput.value) {
@@ -1083,6 +1084,7 @@ define(["emby-input", "emby-button", "emby-checkbox"], function () {
                             config.EnableCredits = page.querySelector('#EnableCredits').checked;
                             config.EnablePreview = page.querySelector('#EnablePreview').checked;
                             config.IgnoreMediaWithExistingSegments = page.querySelector('#IgnoreMediaWithExistingSegments').checked;
+                            config.EnableOnDemandFetch = page.querySelector('#EnableOnDemandFetch').checked;
                             config.EnableAnonymousUsageReporting = page.querySelector('#EnableAnonymousUsageReporting').checked;
                             config.EnableFileLogging = page.querySelector('#EnableFileLogging').checked;
                             return ApiClient.updatePluginConfiguration(pluginUniqueId, config).then(function (result) {
diff --git a/TheIntroDB/EntryPoints/TheIntroDbChapterMarkerPersistenceEntryPoint.cs b/TheIntroDB/EntryPoints/TheIntroDbChapterMarkerPersistenceEntryPoint.cs
index 5a2715a..d636f0e 100644
--- a/TheIntroDB/EntryPoints/TheIntroDbChapterMarkerPersistenceEntryPoint.cs
+++ b/TheIntroDB/EntryPoints/TheIntroDbChapterMarkerPersistenceEntryPoint.cs
@@ -1,6 +1,8 @@
 using System;
 using System.Collections.Concurrent;
 using System.Collections.Generic;
+using System.Linq;
+using System.Threading;
 using System.Threading.Tasks;
 using MediaBrowser.Common.Configuration;
 using MediaBrowser.Controller.Entities;
@@ -13,6 +15,8 @@
 using MediaBrowser.Model.Logging;
 using TheIntroDB.Configuration;
 using TheIntroDB.Data;
+using TheIntroDB.Models;
+using TheIntroDB.Providers;
 using TheIntroDB.Services;
 
 namespace TheIntroDB.EntryPoints
@@ -23,6 +27,7 @@ public sealed class TheIntroDbChapterMarkerPersistenceEntryPoint : IServerEntryP
         private readonly IItemRepository _itemRepository;
         private readonly TheIntroDbSegmentRepository _segmentRepository;
         private readonly TheIntroDbChapterMarkerWriter _chapterWriter;
+        private readonly TheIntroDbSegmentProvider _segmentProvider;
         private readonly ILogger _logger;
 
         private readonly ConcurrentDictionary<long, byte> _writesInProgress = new ConcurrentDictionary<long, byte>();
@@ -38,19 +43,33 @@ public TheIntroDbChapterMarkerPersistenceEntryPoint(
             _logger = Plugin.Instance?.FileLogger ?? logManager.GetLogger("TheIntroDB");
             _segmentRepository = new TheIntroDbSegmentRepository(_logger, applicationPaths);
             _chapterWriter = new TheIntroDbChapterMarkerWriter(_itemRepository, _logger);
+            _segmentProvider = new TheIntroDbSegmentProvider(libraryManager, _logger);
         }
 
         public void Run()
         {
             _libraryManager.ItemUpdated += LibraryManager_ItemUpdated;
+            _libraryManager.ItemAdded += LibraryManager_ItemAdded;
         }
 
         public void Dispose()
         {
             _libraryManager.ItemUpdated -= LibraryManager_ItemUpdated;
+            _libraryManager.ItemAdded -= LibraryManager_ItemAdded;
             _segmentRepository.Dispose();
         }
 
+        private void LibraryManager_ItemAdded(object sender, ItemChangeEventArgs e)
+        {
+            var item = e?.Item;
+            if (item is null)
+            {
+                return;
+            }
+
+            _ = OnDemandFetchAsync(item, "item_added");
+        }
+
         private void LibraryManager_ItemUpdated(object sender, ItemChangeEventArgs e)
         {
             try
@@ -78,6 +97,9 @@ private void LibraryManager_ItemUpdated(object sender, ItemChangeEventArgs e)
                     return;
                 }
 
+                // Also trigger on-demand fetch for updated items that have no segments yet
+                _ = OnDemandFetchAsync(item, "item_updated");
+
                 _ = Task.Run(() => EnsureMarkersApplied(item, config));
             }
             catch (Exception ex)
@@ -179,5 +201,54 @@ private static bool NeedsMarkerApply(IReadOnlyList<ChapterInfo> chapters, Plugin
 
             return !(hasIntro && hasRecap && hasCredits && hasPreview);
         }
+
+        private async Task OnDemandFetchAsync(BaseItem item, string trigger)
+        {
+            try
+            {
+                var config = Plugin.Instance?.Configuration;
+                if (config == null || !config.EnableOnDemandFetch)
+                {
+                    return;
+                }
+
+                var internalId = item.InternalId;
+
+                // Check if segments already exist
+                var existing = _segmentRepository.GetSegments(internalId);
+                if (existing != null && existing.Count > 0)
+                {
+                    _logger.Debug("On-demand fetch skipped ({0}): segments already exist for {1}", trigger, item.Name);
+                    return;
+                }
+
+                _logger.Info("On-demand segment fetch triggered ({0}) for {1} ({2})", trigger, item.Name, item.GetType().Name);
+
+                var result = await _segmentProvider.GetMediaSegmentsAsync(item.Id, CancellationToken.None).ConfigureAwait(false);
+
+                if (result.Segments == null || result.Segments.Count == 0)
+                {
+                    _logger.Info("On-demand segment fetch ({0}): no segments returned for {1}", trigger, item.Name);
+                    return;
+                }
+
+                var storedSegments = result.Segments.Select(s => new StoredMediaSegment
+                {
+                    ItemInternalId = internalId,
+                    Type = s.Type,
+                    StartTicks = s.StartTicks,
+                    EndTicks = s.EndTicks
+                }).ToList();
+
+                _segmentRepository.ReplaceSegments(internalId, storedSegments, DateTime.UtcNow);
+                _chapterWriter.ApplyMarkers(item, storedSegments, config);
+
+                _logger.Info("On-demand segment fetch completed ({0}) for {1}: {2} segments, markers applied", trigger, item.Name, storedSegments.Count);
+            }
+            catch (Exception ex)
+            {
+                _logger.Error("On-demand segment fetch failed ({0}) for {1}: {2}", trigger, item?.Name ?? "null", ex.Message);
+            }
+        }
     }
 }
diff --git a/TheIntroDB/EntryPoints/TheIntroDbUsageReportingEntryPoint.cs b/TheIntroDB/EntryPoints/TheIntroDbUsageReportingEntryPoint.cs
index 1f8f981..dbf3f3c 100644
--- a/TheIntroDB/EntryPoints/TheIntroDbUsageReportingEntryPoint.cs
+++ b/TheIntroDB/EntryPoints/TheIntroDbUsageReportingEntryPoint.cs
@@ -2,14 +2,18 @@
 using System.Collections.Concurrent;
 using System.Collections.Generic;
 using System.Globalization;
+using System.Linq;
+using System.Threading;
 using System.Threading.Tasks;
 using MediaBrowser.Common.Configuration;
+using MediaBrowser.Controller.Entities;
 using MediaBrowser.Controller.Library;
 using MediaBrowser.Controller.Plugins;
 using MediaBrowser.Controller.Session;
 using MediaBrowser.Model.Logging;
 using TheIntroDB.Data;
 using TheIntroDB.Models;
+using TheIntroDB.Providers;
 
 namespace TheIntroDB.EntryPoints
 {
@@ -21,15 +25,18 @@ public class TheIntroDbUsageReportingEntryPoint : IServerEntryPoint
 
         private readonly ISessionManager _sessionManager;
         private readonly TheIntroDbSegmentRepository _repository;
+        private readonly ILibraryManager _libraryManager;
         private readonly ILogger _logger;
         private readonly ConcurrentDictionary<string, PlaybackState> _states = new ConcurrentDictionary<string, PlaybackState>();
 
         public TheIntroDbUsageReportingEntryPoint(
             ISessionManager sessionManager,
             IApplicationPaths applicationPaths,
+            ILibraryManager libraryManager,
             ILogManager logManager)
         {
             _sessionManager = sessionManager;
+            _libraryManager = libraryManager;
             _logger = Plugin.Instance?.FileLogger ?? logManager.GetLogger("TheIntroDB");
             _repository = new TheIntroDbSegmentRepository(_logger, applicationPaths);
         }
@@ -54,12 +61,14 @@ public void Run()
             });
             _sessionManager.PlaybackProgress += SessionManager_PlaybackProgress;
             _sessionManager.PlaybackStopped += SessionManager_PlaybackStopped;
+            _sessionManager.PlaybackStart += SessionManager_PlaybackStart;
         }
 
         public void Dispose()
         {
             _sessionManager.PlaybackProgress -= SessionManager_PlaybackProgress;
             _sessionManager.PlaybackStopped -= SessionManager_PlaybackStopped;
+            _sessionManager.PlaybackStart -= SessionManager_PlaybackStart;
             _repository.Dispose();
         }
 
@@ -162,6 +171,68 @@ private void SessionManager_PlaybackProgress(object sender, PlaybackProgressEven
             }
         }
 
+        private void SessionManager_PlaybackStart(object sender, PlaybackProgressEventArgs e)
+        {
+            try
+            {
+                if (e?.Item == null)
+                {
+                    return;
+                }
+
+                var item = e.Item;
+                var config = Plugin.Instance?.Configuration;
+                if (config == null || !config.EnableOnDemandFetch)
+                {
+                    return;
+                }
+
+                var internalId = item.InternalId;
+                var existingSegments = _repository.GetSegments(internalId);
+                if (existingSegments != null && existingSegments.Count > 0)
+                {
+                    return;
+                }
+
+                _logger.Info("On-demand segment fetch triggered (playback_start) for {0} ({1})", item.Name, item.GetType().Name);
+
+                _ = Task.Run(async () =>
+                {
+                    try
+                    {
+                        var provider = new TheIntroDbSegmentProvider(_libraryManager, _logger);
+                        var result = await provider.GetMediaSegmentsAsync(item.Id, CancellationToken.None).ConfigureAwait(false);
+
+                        if (result.Segments == null || result.Segments.Count == 0)
+                        {
+                            _logger.Info("On-demand segment fetch (playback_start): no segments returned for {0}", item.Name);
+                            return;
+                        }
+
+                        var storedSegments = result.Segments.Select(s => new StoredMediaSegment
+                        {
+                            ItemInternalId = internalId,
+                            Type = s.Type,
+                            StartTicks = s.StartTicks,
+                            EndTicks = s.EndTicks
+                        }).ToList();
+
+                        _repository.ReplaceSegments(internalId, storedSegments, DateTime.UtcNow);
+
+                        _logger.Info("On-demand segment fetch completed (playback_start) for {0}: {1} segments", item.Name, storedSegments.Count);
+                    }
+                    catch (Exception ex)
+                    {
+                        _logger.Error("On-demand segment fetch failed (playback_start) for {0}: {1}", item?.Name ?? "null", ex.Message);
+                    }
+                });
+            }
+            catch (Exception ex)
+            {
+                _logger.Error("PlaybackStart handler exception: " + ex.Message);
+            }
+        }
+
         private sealed class PlaybackState
         {
             public long ItemInternalId;
diff --git a/TheIntroDB/Providers/TheIntroDbSegmentProvider.cs b/TheIntroDB/Providers/TheIntroDbSegmentProvider.cs
index 8d9a481..8c5d28a 100644
--- a/TheIntroDB/Providers/TheIntroDbSegmentProvider.cs
+++ b/TheIntroDB/Providers/TheIntroDbSegmentProvider.cs
@@ -102,6 +102,16 @@ public async Task<SegmentFetchResult> GetMediaSegmentsAsync(
                 _logger.Info("Episode: Name={0}, Series={1}, S{2}E{3}, TmdbId={4}, TvdbId={5}, ImdbId={6}",
                   item.Name, ep.SeriesName, season, episode, tmdbId, tvdbId, imdbId ?? "(none)");
             }
+            else if (item is Video video)
+            {
+                isMovie = false;
+                tmdbId = GetTmdbId(video);
+                tvdbId = GetTvdbId(video);
+                imdbId = GetImdbId(video);
+                season = video.ParentIndexNumber;
+                episode = video.IndexNumber;
+                _logger.Info("Video: Name={0}, TmdbId={1}, TvdbId={2}, ImdbId={3}, Season={4}, Episode={5}", item.Name, tmdbId, tvdbId, imdbId ?? "(none)", season, episode);
+            }
 
             if ((!tmdbId.HasValue || tmdbId.Value <= 0) && (!tvdbId.HasValue || tvdbId.Value <= 0) && string.IsNullOrWhiteSpace(imdbId))
             {
@@ -209,7 +219,7 @@ public async Task<SegmentFetchResult> GetMediaSegmentsAsync(
         /// <returns>True if the item is supported (Movie or Episode).</returns>
         public bool Supports(BaseItem item)
         {
-            var supported = item is Episode || item is Movie;
+            var supported = item is Episode || item is Movie || item is Video;
             _logger.Debug("Supports({0}, {1}): {2}", item?.Name ?? "null", item?.GetType().Name ?? "null", supported);
             return supported;
         }