diff --git a/Source/FileManager/FileSystemTest.cs b/Source/FileManager/FileSystemTest.cs
new file mode 100644
index 00000000..eef4ea28
--- /dev/null
+++ b/Source/FileManager/FileSystemTest.cs
@@ -0,0 +1,74 @@
+using System;
+using System.IO;
+
+namespace FileManager
+{
+	public static class FileSystemTest
+	{
+		/// <summary>
+		/// Additional characters which are illegal for filenames in Windows environments.
+		/// Double quotes and slashes are already illegal filename characters on all platforms,
+		/// so they are not included here.
+		/// </summary>
+		public static string AdditionalInvalidWindowsFilenameCharacters { get; } = "<>|:*?";
+
+		/// <summary>
+		/// Test if the directory supports filenames with characters that are invalid on Windows (:, *, ?, &lt;, &gt;, |).
+		/// </summary>
+		public static bool CanWriteWindowsInvalidChars(LongPath directoryName)
+		{
+			var testFile = Path.Combine(directoryName, AdditionalInvalidWindowsFilenameCharacters + Guid.NewGuid().ToString());
+			return CanWriteFile(testFile);
+		}
+
+		/// <summary>
+		/// Test if the directory supports filenames with 255 unicode characters.
+		/// </summary>
+		public static bool CanWrite255UnicodeChars(LongPath directoryName)
+		{
+			const char unicodeChar = 'ü';
+			var testFileName = new string(unicodeChar, 255);
+			var testFile = Path.Combine(directoryName, testFileName);
+			return CanWriteFile(testFile);
+		}
+
+		/// <summary>
+		/// Test if a directory has write access by attempting to create an empty file in it.
+		/// <para/>Returns true even if the temporary file can not be deleted.
+		/// </summary>
+		public static bool CanWriteDirectory(LongPath directoryName)
+		{
+			if (!Directory.Exists(directoryName))
+				return false;
+
+			Serilog.Log.Logger.Debug("Testing write permissions for directory: {@DirectoryName}", directoryName);
+			var testFilePath = Path.Combine(directoryName, Guid.NewGuid().ToString());
+			return CanWriteFile(testFilePath);
+		}
+
+		private static bool CanWriteFile(LongPath filename)
+		{
+			try
+			{
+				Serilog.Log.Logger.Debug("Testing ability to write filename: {@filename}", filename);
+				File.WriteAllBytes(filename, []);
+				Serilog.Log.Logger.Debug("Deleting test file after successful write: {@filename}", filename);
+				try
+				{
+					FileUtility.SaferDelete(filename);
+				}
+				catch (Exception ex)
+				{
+					//An error deleting the file doesn't constitute a write failure.
+					Serilog.Log.Logger.Debug(ex, "Error deleting test file: {@filename}", filename);
+				}
+				return true;
+			}
+			catch (Exception ex)
+			{
+				Serilog.Log.Logger.Debug(ex, "Error writing test file: {@filename}", filename);
+				return false;
+			}
+		}
+	}
+}
diff --git a/Source/LibationAvalonia/Views/MainWindow.axaml.cs b/Source/LibationAvalonia/Views/MainWindow.axaml.cs
index 63a35da1..f36d8cf7 100644
--- a/Source/LibationAvalonia/Views/MainWindow.axaml.cs
+++ b/Source/LibationAvalonia/Views/MainWindow.axaml.cs
@@ -43,6 +43,38 @@ namespace LibationAvalonia.Views
 				KeyBindings.Add(new KeyBinding { Command = ReactiveCommand.Create(ViewModel.ShowAccountsAsync), Gesture = new KeyGesture(Key.A, KeyModifiers.Control | KeyModifiers.Shift) });
 				KeyBindings.Add(new KeyBinding { Command = ReactiveCommand.Create(ViewModel.ExportLibraryAsync), Gesture = new KeyGesture(Key.S, KeyModifiers.Control) });
 			}
+
+			Configuration.Instance.PropertyChanged += Settings_PropertyChanged;
+			Settings_PropertyChanged(this, null);
+		}
+
+		[Dinah.Core.PropertyChangeFilter(nameof(Configuration.Books))]
+		private void Settings_PropertyChanged(object sender, Dinah.Core.PropertyChangedEventArgsEx e)
+		{
+			if (!Configuration.IsWindows && !Configuration.Instance.BooksCanWriteWindowsInvalidChars)
+			{
+				//The books directory does not support filenames with windows' invalid characters.
+				//Ensure that the ReplacementCharacters configuration has replacements for all invalid characters.
+				//We can't rely on the "other invalid characters" replacement because that is only used by
+				//ReplacementCharacters for platform-specific illegal characters, whereas for the Books directory
+				//we are concerned with the ultimate destination directory's capabilities. 
+				var defaults = ReplacementCharacters.Default(true).Replacements;
+				var replacements = Configuration.Instance.ReplacementCharacters.Replacements.ToList();
+				bool changed = false;
+				foreach (var c in FileSystemTest.AdditionalInvalidWindowsFilenameCharacters)
+				{
+					if (!replacements.Any(r => r.CharacterToReplace == c))
+					{
+						var replacement = defaults.FirstOrDefault(r => r.CharacterToReplace == c) ?? defaults[0];
+						replacements.Add(replacement);
+						changed = true;
+					}
+				}
+				if (changed)
+				{
+					Configuration.Instance.ReplacementCharacters = new ReplacementCharacters { Replacements = replacements };
+				}
+			}
 		}
 
 		private void AudibleApiStorage_LoadError(object sender, AccountSettingsLoadErrorEventArgs e)
diff --git a/Source/LibationFileManager/Configuration.PersistentSettings.cs b/Source/LibationFileManager/Configuration.PersistentSettings.cs
index eb648b3d..be4a5a7e 100644
--- a/Source/LibationFileManager/Configuration.PersistentSettings.cs
+++ b/Source/LibationFileManager/Configuration.PersistentSettings.cs
@@ -111,7 +111,34 @@ namespace LibationFileManager
 		public bool BetaOptIn { get => GetNonString(defaultValue: false); set => SetNonString(value); }
 
 		[Description("Location for book storage. Includes destination of newly liberated books")]
-		public LongPath? Books { get => GetString(); set => SetString(value); }
+		public LongPath? Books {
+			get => GetString();
+			set
+			{
+				if (value != Books)
+				{
+					OnPropertyChanging(nameof(Books), Books, value);
+					Settings.SetString(nameof(Books), value);
+					m_BooksCanWrite255UnicodeChars = null;
+					m_BooksCanWriteWindowsInvalidChars = null;
+					OnPropertyChanged(nameof(Books), value);
+				}
+			}
+		}
+
+		private bool? m_BooksCanWrite255UnicodeChars;
+		private bool? m_BooksCanWriteWindowsInvalidChars;
+		/// <summary>
+		/// True if the Books directory can be written to with 255 unicode character filenames
+		/// <para/> Does not persist. Check and set this value at runtime and whenever Books is changed.
+		/// </summary>
+		public bool BooksCanWrite255UnicodeChars => m_BooksCanWrite255UnicodeChars ??= FileSystemTest.CanWrite255UnicodeChars(Books);
+		/// <summary>
+		/// True if the Books directory can be written to with filenames containing characters invalid on Windows (:, *, ?, &lt;, &gt;, |)
+		/// <para/> Always false on Windows platforms.
+		/// <para/> Does not persist. Check and set this value at runtime and whenever Books is changed.
+		/// </summary>
+		public bool BooksCanWriteWindowsInvalidChars => !IsWindows && (m_BooksCanWriteWindowsInvalidChars ??= FileSystemTest.CanWriteWindowsInvalidChars(Books));
 
 		[Description("Overwrite existing files if they already exist?")]
 		public bool OverwriteExisting { get => GetNonString(defaultValue: false); set => SetNonString(value); }
diff --git a/Source/LibationFileManager/Templates/Templates.cs b/Source/LibationFileManager/Templates/Templates.cs
index ac0af0fa..5b36ae1a 100644
--- a/Source/LibationFileManager/Templates/Templates.cs
+++ b/Source/LibationFileManager/Templates/Templates.cs
@@ -157,7 +157,7 @@ namespace LibationFileManager.Templates
 				var maxFilenameLength = LongPath.MaxFilenameLength -
 					(i < pathParts.Count - 1 || string.IsNullOrEmpty(fileExtension) ? 0 : fileExtension.Length + 5);
 
-				while (part.Sum(LongPath.GetFilesystemStringLength) > maxFilenameLength)
+				while (part.Sum(GetFilenameLength) > maxFilenameLength)
 				{
 					int maxLength = part.Max(p => p.Length);
 					var maxEntry = part.First(p => p.Length == maxLength);
@@ -173,6 +173,10 @@ namespace LibationFileManager.Templates
 			return FileUtility.GetValidFilename(fullPath, replacements, fileExtension, returnFirstExisting);
 		}
 
+		private static int GetFilenameLength(string filename)
+			=> Configuration.Instance.BooksCanWrite255UnicodeChars ? filename.Length
+			: System.Text.Encoding.UTF8.GetByteCount(filename);
+
 		/// <summary>
 		/// Organize template parts into directories. Any Extra slashes will be
 		/// returned as empty directories and are taken care of by Path.Combine()
diff --git a/Source/_Tests/LibationFileManager.Tests/TemplatesTests.cs b/Source/_Tests/LibationFileManager.Tests/TemplatesTests.cs
index 4d8aa485..cb853d15 100644
--- a/Source/_Tests/LibationFileManager.Tests/TemplatesTests.cs
+++ b/Source/_Tests/LibationFileManager.Tests/TemplatesTests.cs
@@ -23,6 +23,15 @@ namespace TemplatesTests
 
 	public static class Shared
 	{
+		[System.Runtime.CompilerServices.ModuleInitializer]
+		public static void Init()
+		{
+			var thisDir = Path.GetDirectoryName(Environment.ProcessPath);
+			LibationFileManager.Configuration.SetLibationFiles(thisDir);
+			if (!LibationFileManager.Configuration.Instance.LibationSettingsAreValid)
+				LibationFileManager.Configuration.Instance.Books = Path.Combine(thisDir, "Books");
+		}
+
 		public static LibraryBookDto GetLibraryBook()
 			=> GetLibraryBook([new SeriesDto("Sherlock Holmes", "1", "B08376S3R2")]);