diff --git a/Source/FileManager/ReplacementCharacters.cs b/Source/FileManager/ReplacementCharacters.cs
index cc93451b..8c11b10d 100644
--- a/Source/FileManager/ReplacementCharacters.cs
+++ b/Source/FileManager/ReplacementCharacters.cs
@@ -61,59 +61,97 @@ namespace FileManager
 	[JsonConverter(typeof(ReplacementCharactersConverter))]
 	public class ReplacementCharacters
 	{
-		public static readonly ReplacementCharacters Default = new()
+		static ReplacementCharacters()
 		{
-			Replacements = new List<Replacement>()
-			{
-				Replacement.OtherInvalid("_"),
-				Replacement.FilenameForwardSlash("∕"),
-				Replacement.FilenameBackSlash(""),
-				Replacement.OpenQuote("“"),
-				Replacement.CloseQuote("”"),
-				Replacement.OtherQuote("＂"),
-				Replacement.OpenAngleBracket("＜"),
-				Replacement.CloseAngleBracket("＞"),
-				Replacement.Colon("꞉"),
-				Replacement.Asterisk("✱"),
-				Replacement.QuestionMark("？"),
-				Replacement.Pipe("⏐"),
-			}
-		};
 
-		public static readonly ReplacementCharacters LoFiDefault = new()
-		{
-			Replacements = new List<Replacement>()
+		}
+		public static readonly ReplacementCharacters Default
+			= IsWindows
+			? new()
 			{
-				Replacement.OtherInvalid("_"),
-				Replacement.FilenameForwardSlash("_"),
-				Replacement.FilenameBackSlash("_"),
-				Replacement.OpenQuote("'"),
-				Replacement.CloseQuote("'"),
-				Replacement.OtherQuote("'"),
-				Replacement.OpenAngleBracket("{"),
-				Replacement.CloseAngleBracket("}"),
-				Replacement.Colon("-"),
+				Replacements = new List<Replacement>()
+				{
+					Replacement.OtherInvalid("_"),
+					Replacement.FilenameForwardSlash("∕"),
+					Replacement.FilenameBackSlash(""),
+					Replacement.OpenQuote("“"),
+					Replacement.CloseQuote("”"),
+					Replacement.OtherQuote("＂"),
+					Replacement.OpenAngleBracket("＜"),
+					Replacement.CloseAngleBracket("＞"),
+					Replacement.Colon("꞉"),
+					Replacement.Asterisk("✱"),
+					Replacement.QuestionMark("？"),
+					Replacement.Pipe("⏐"),
+				}
 			}
-		};
-
-		public static readonly ReplacementCharacters Barebones = new()
-		{
-			Replacements = new List<Replacement>()
+			: new()
 			{
-				Replacement.OtherInvalid("_"),
-				Replacement.FilenameForwardSlash("_"),
-				Replacement.FilenameBackSlash("_"),
-				Replacement.OpenQuote("_"),
-				Replacement.CloseQuote("_"),
-				Replacement.OtherQuote("_"),
-			}
-		};
+				Replacements = new List<Replacement>()
+				{
+					Replacement.OtherInvalid("_"),
+					Replacement.FilenameForwardSlash("∕"),
+					Replacement.FilenameBackSlash(""),
+					Replacement.OpenQuote("“"),
+					Replacement.CloseQuote("”"),
+					Replacement.OtherQuote("＂")
+				}
+			};
 
-		private static readonly char[] invalidChars = Path.GetInvalidPathChars().Union(new[] {
-				'*', '?', ':',
-				// these are weird. If you run Path.GetInvalidPathChars() in Visual Studio's "C# Interactive", then these characters are included.
-				// In live code, Path.GetInvalidPathChars() does not include them
-				'"', '<', '>'
+		public static readonly ReplacementCharacters LoFiDefault
+			= IsWindows
+			? new()
+			{
+				Replacements = new List<Replacement>()
+				{
+					Replacement.OtherInvalid("_"),
+					Replacement.FilenameForwardSlash("_"),
+					Replacement.FilenameBackSlash("_"),
+					Replacement.OpenQuote("'"),
+					Replacement.CloseQuote("'"),
+					Replacement.OtherQuote("'"),
+					Replacement.OpenAngleBracket("{"),
+					Replacement.CloseAngleBracket("}"),
+					Replacement.Colon("-"),
+				}
+			}
+			: Barebones;
+
+		public static readonly ReplacementCharacters Barebones
+			= IsWindows
+			? new ()
+			{
+				Replacements = new List<Replacement>()
+				{
+					Replacement.OtherInvalid("_"),
+					Replacement.FilenameForwardSlash("_"),
+					Replacement.FilenameBackSlash("_"),
+					Replacement.OpenQuote("_"),
+					Replacement.CloseQuote("_"),
+					Replacement.OtherQuote("_")
+				}
+			}
+			: new ()
+			{
+				Replacements = new List<Replacement>()
+				{
+					Replacement.OtherInvalid("_"),
+					Replacement.FilenameForwardSlash("_"),
+					Replacement.FilenameBackSlash("\\"),
+					Replacement.OpenQuote("\""),
+					Replacement.CloseQuote("\""),
+					Replacement.OtherQuote("\"")
+				}
+			};
+
+		private static bool IsWindows => Environment.OSVersion.Platform is PlatformID.Win32NT;
+
+		private static readonly char[] invalidPathChars = Path.GetInvalidFileNameChars().Except(new[] {
+				'\\', '/'
+			}).ToArray();
+
+		private static readonly char[] invalidSlashes = Path.GetInvalidFileNameChars().Intersect(new[] {
+				'\\', '/'
 			}).ToArray();
 
 		public IReadOnlyList<Replacement> Replacements { get; init; }
@@ -126,10 +164,13 @@ namespace FileManager
 
 		private string GetFilenameCharReplacement(char toReplace, char preceding, char succeding)
 		{
-			if (toReplace == ForwardSlash.CharacterToReplace)
-				return ForwardSlash.ReplacementString;
-			else if (toReplace == BackSlash.CharacterToReplace)
-				return BackSlash.ReplacementString;
+			if (invalidSlashes.Contains(toReplace))
+			{
+				if (toReplace == ForwardSlash.CharacterToReplace)
+					return ForwardSlash.ReplacementString;
+				else
+					return BackSlash.ReplacementString;
+			}
 			else return GetPathCharReplacement(toReplace, preceding, succeding);
 		}
 		private string GetPathCharReplacement(char toReplace, char preceding, char succeding)
@@ -158,6 +199,7 @@ namespace FileManager
 					return OtherQuote;
 			}
 
+			//Replace any other non-mandatory characters
 			for (int i = Replacement.FIXED_COUNT; i < Replacements.Count; i++)
 			{
 				var r = Replacements[i];
@@ -167,11 +209,10 @@ namespace FileManager
 			return DefaultReplacement;
 		}
 
-
 		public static bool ContainsInvalidPathChar(string path)
-			=> path.Any(c => invalidChars?.Contains(c) == true);
+			=> path.Any(c => invalidPathChars.Contains(c));
 		public static bool ContainsInvalidFilenameChar(string path)
-			=> path.Any(c => invalidChars?.Concat(new char[] { '\\', '/' })?.Contains(c) == true);
+			=> ContainsInvalidPathChar(path) || path.Any(c => invalidSlashes.Contains(c));
 
 		public string ReplaceInvalidFilenameChars(string fileName)
 		{
@@ -181,7 +222,7 @@ namespace FileManager
 			{
 				var c = fileName[i];
 
-				if (invalidChars.Contains(c) || c == ForwardSlash.CharacterToReplace || c == BackSlash.CharacterToReplace)
+				if (invalidPathChars.Contains(c) || invalidSlashes.Contains(c))
 				{
 					char preceding = i > 0 ? fileName[i - 1] : default;
 					char succeeding = i < fileName.Length - 1 ? fileName[i + 1] : default;
@@ -204,7 +245,7 @@ namespace FileManager
 			{
 				var c = pathStr[i];
 
-				if (!invalidChars.Contains(c) || (c == ':' && i == 1 && Path.IsPathRooted(pathStr)))
+				if (!invalidPathChars.Contains(c) || (c == ':' && i == 1 && Path.IsPathRooted(pathStr)))
 					builder.Append(c);
 				else
 				{
@@ -212,7 +253,6 @@ namespace FileManager
 					char succeeding = i < pathStr.Length - 1 ? pathStr[i + 1] : default;
 					builder.Append(GetPathCharReplacement(c, preceding, succeeding));
 				}
-
 			}
 			return builder.ToString();
 		}
@@ -248,7 +288,7 @@ namespace FileManager
 				dict[3].CharacterToReplace != default3.CharacterToReplace || dict[3].Description != default3.Description ||
 				dict[4].CharacterToReplace != default4.CharacterToReplace || dict[4].Description != default4.Description ||
 				dict[5].CharacterToReplace != default5.CharacterToReplace || dict[5].Description != default5.Description ||
-				dict.Any(r => ReplacementCharacters.ContainsInvalidPathChar(r.ReplacementString))
+				dict.Any(r => ReplacementCharacters.ContainsInvalidFilenameChar(r.ReplacementString))
 				)
 			{
 				dict = ReplacementCharacters.Default.Replacements;
diff --git a/Source/LibationAvalonia/Dialogs/EditReplacementChars.axaml.cs b/Source/LibationAvalonia/Dialogs/EditReplacementChars.axaml.cs
index 5524678e..d6905e9e 100644
--- a/Source/LibationAvalonia/Dialogs/EditReplacementChars.axaml.cs
+++ b/Source/LibationAvalonia/Dialogs/EditReplacementChars.axaml.cs
@@ -143,7 +143,7 @@ namespace LibationAvalonia.Dialogs
 				get => _replacementText;
 				set
 				{
-					if (ReplacementCharacters.ContainsInvalidPathChar(value))
+					if (ReplacementCharacters.ContainsInvalidFilenameChar(value))
 						this.RaisePropertyChanged(nameof(ReplacementText));
 					else
 						this.RaiseAndSetIfChanged(ref _replacementText, value);
@@ -158,7 +158,7 @@ namespace LibationAvalonia.Dialogs
 
 				set
 				{
-					if (value?.Length != 1 || !ReplacementCharacters.ContainsInvalidPathChar(value))
+					if (value?.Length != 1 || !ReplacementCharacters.ContainsInvalidFilenameChar(value))
 						this.RaisePropertyChanged(nameof(CharacterToReplace));
 					else
 					{
diff --git a/Source/LibationWinForms/Dialogs/EditReplacementChars.cs b/Source/LibationWinForms/Dialogs/EditReplacementChars.cs
index a24b4371..75762a90 100644
--- a/Source/LibationWinForms/Dialogs/EditReplacementChars.cs
+++ b/Source/LibationWinForms/Dialogs/EditReplacementChars.cs
@@ -101,7 +101,7 @@ namespace LibationWinForms.Dialogs
 			{
 				dataGridView1.Rows[e.RowIndex].ErrorText = $"The {charToReplaceStr[0]} character is already being replaced";
 			}
-			else if (ReplacementCharacters.ContainsInvalidPathChar(replacement))
+			else if (ReplacementCharacters.ContainsInvalidFilenameChar(replacement))
 			{
 				dataGridView1.Rows[e.RowIndex].ErrorText = $"Your {replacementStringCol.HeaderText} contains illegal characters";
 			}