diff --git a/listenarr.api/Features/Library/LibraryQueryWorkflow.cs b/listenarr.api/Features/Library/LibraryQueryWorkflow.cs
index 51899ec77..7e94c8f6d 100644
--- a/listenarr.api/Features/Library/LibraryQueryWorkflow.cs
+++ b/listenarr.api/Features/Library/LibraryQueryWorkflow.cs
@@ -8,6 +8,7 @@
  * (at your option) any later version.
  */
 using Microsoft.AspNetCore.Mvc;
+using Listenarr.Domain.Common;
 
 namespace Listenarr.Api.Features.Library;
 
@@ -94,7 +95,7 @@ public async Task<IActionResult> GetFilesDebugAsync(int id) =>
             })
             .ToList(),
         tags = audiobook.Tags,
-        files = audiobook.Files?.Select(file => new
+        files = AudiobookFileOrdering.InNaturalOrder(audiobook.Files).Select(file => new
         {
             id = file.Id,
             path = file.Path,
diff --git a/listenarr.application/Mapping/AudiobookDtoFactory.cs b/listenarr.application/Mapping/AudiobookDtoFactory.cs
index 47d55850e..2911b18de 100644
--- a/listenarr.application/Mapping/AudiobookDtoFactory.cs
+++ b/listenarr.application/Mapping/AudiobookDtoFactory.cs
@@ -16,6 +16,8 @@
  * along with this program. If not, see <https://www.gnu.org/licenses/>.
  */
 
+using Listenarr.Domain.Common;
+
 namespace Listenarr.Application.Mapping
 {
     public static class AudiobookDtoFactory
@@ -24,7 +26,7 @@ public static AudiobookDto BuildFromEntity(Audiobook audiobook)
         {
             if (audiobook == null) return null!;
 
-            var files = audiobook.Files?.Select(f => new AudiobookFileDto
+            var files = AudiobookFileOrdering.InNaturalOrder(audiobook.Files).Select(f => new AudiobookFileDto
             {
                 Id = f.Id,
                 Path = f.Path,
diff --git a/listenarr.domain/Common/AudiobookFileOrdering.cs b/listenarr.domain/Common/AudiobookFileOrdering.cs
new file mode 100644
index 000000000..02452ec49
--- /dev/null
+++ b/listenarr.domain/Common/AudiobookFileOrdering.cs
@@ -0,0 +1,66 @@
+/*
+ * Listenarr - Audiobook Management System
+ * Copyright (C) 2024-2026 Listenarr Contributors
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as published
+ * by the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program. If not, see <https://www.gnu.org/licenses/>.
+ */
+
+namespace Listenarr.Domain.Common
+{
+    /// <summary>
+    /// Canonical ordering for the file list attached to an audiobook.
+    ///
+    /// EF returns audiobook files in essentially undefined (row-insertion / scan)
+    /// order, which surfaces in the UI as a jumbled file list — "Disc 08, 01, 06,
+    /// 10, 07, 09, 11, 12, 03..." for a 14-disc rip. Every API response that
+    /// projects <see cref="Audiobook.Files"/> for the frontend should pass it
+    /// through <see cref="InNaturalOrder"/> so the user sees a stable,
+    /// human-natural sequence.
+    ///
+    /// Currently used by:
+    ///  - <c>LibraryController.GetAudiobook</c> (the FE audiobook-detail endpoint)
+    ///  - <c>AudiobookDtoFactory.BuildFromEntity</c> (scan SignalR broadcasts, move ops)
+    /// </summary>
+    public static class AudiobookFileOrdering
+    {
+        /// <summary>
+        /// Return the supplied files sorted by filename using a natural-sort key
+        /// (so "Disc 02" precedes "Disc 10"). Files without a path sink to the
+        /// end so any caller defaulting to <c>files[0]</c> as a preview source
+        /// still picks something playable. Returns an empty enumerable for null
+        /// input — callers can chain <c>.Select(...).ToArray()</c> safely.
+        /// </summary>
+        public static IEnumerable<AudiobookFile> InNaturalOrder(IEnumerable<AudiobookFile>? source)
+        {
+            if (source == null) return Array.Empty<AudiobookFile>();
+
+            return source
+                .OrderBy(f => string.IsNullOrEmpty(f.Path) ? 1 : 0)
+                .ThenBy(f => NaturalSort.ToKey(GetFileNameForSort(f.Path)), StringComparer.Ordinal)
+                .ThenBy(f => f.Path ?? string.Empty, StringComparer.OrdinalIgnoreCase)
+                .ThenBy(f => f.Id);
+        }
+
+        // Use just the filename for natural-sort purposes — directory separators in
+        // the full path would otherwise dominate the key and group files by folder
+        // instead of by name. Handles both forward and back slashes so Windows-rooted
+        // paths from the importer sort the same as Unix paths from the scanner.
+        private static string GetFileNameForSort(string? path)
+        {
+            if (string.IsNullOrEmpty(path)) return string.Empty;
+            var lastSlash = path.LastIndexOfAny(new[] { '/', '\\' });
+            return lastSlash < 0 ? path : path[(lastSlash + 1)..];
+        }
+    }
+}
diff --git a/listenarr.domain/Common/NaturalSort.cs b/listenarr.domain/Common/NaturalSort.cs
new file mode 100644
index 000000000..d7e4636c1
--- /dev/null
+++ b/listenarr.domain/Common/NaturalSort.cs
@@ -0,0 +1,61 @@
+/*
+ * Listenarr - Audiobook Management System
+ * Copyright (C) 2024-2026 Listenarr Contributors
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as published
+ * by the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program. If not, see <https://www.gnu.org/licenses/>.
+ */
+using System.Text.RegularExpressions;
+
+namespace Listenarr.Domain.Common
+{
+    /// <summary>
+    /// Natural-sort helpers that treat embedded digit runs as numeric values so that
+    /// strings like "Disc 2" sort before "Disc 10" (rather than the lexicographic
+    /// "Disc 10" before "Disc 2" you would get from ordinary string comparison).
+    ///
+    /// Used wherever a user-visible list of files, chapters, or numbered items needs
+    /// to come out in the order a human would expect.
+    /// </summary>
+    public static class NaturalSort
+    {
+        // Splits a string into alternating runs of digits and non-digits so the key
+        // builder can pad numeric runs to a fixed width before concatenation.
+        private static readonly Regex NumericChunkPattern = new(@"\d+|\D+", RegexOptions.Compiled);
+
+        /// <summary>
+        /// Build a comparison key for <paramref name="value"/> such that ordinary
+        /// ordinal string comparison on the returned key produces a natural sort.
+        ///
+        /// Numeric runs are zero-padded to 12 digits (large enough for any realistic
+        /// chapter / disc / track number) and non-numeric runs are upper-cased for
+        /// case-insensitive ordering.
+        /// </summary>
+        public static string ToKey(string? value)
+        {
+            if (string.IsNullOrEmpty(value))
+            {
+                return string.Empty;
+            }
+
+            return string.Concat(
+                NumericChunkPattern.Matches(value).Select(match =>
+                {
+                    var chunk = match.Value;
+                    return int.TryParse(chunk, out var numeric)
+                        ? numeric.ToString("D12")
+                        : chunk.ToUpperInvariant();
+                }));
+        }
+    }
+}