diff --git a/CHANGELOG.md b/CHANGELOG.md
index d9aee728f..967687b11 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,6 +13,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 - Fix bug scheduling mid-roll filler with content that contains one chapter
   - No mid-roll filler will be inserted for content with zero or one chapters
 - Fix thread sync bug with `HLS Segmenter` (and `MPEG-TS`) streaming modes
+- Fix path replacement bug when media server path is left blank
 
 ### Added
 - Add automated error reporting via Bugsnag
diff --git a/ErsatzTV.Core.Tests/Emby/EmbyPathReplacementServiceTests.cs b/ErsatzTV.Core.Tests/Emby/EmbyPathReplacementServiceTests.cs
new file mode 100644
index 000000000..3b33a1695
--- /dev/null
+++ b/ErsatzTV.Core.Tests/Emby/EmbyPathReplacementServiceTests.cs
@@ -0,0 +1,271 @@
+using System.Runtime.InteropServices;
+using ErsatzTV.Core.Domain;
+using ErsatzTV.Core.Interfaces.Repositories;
+using ErsatzTV.Core.Interfaces.Runtime;
+using ErsatzTV.Core.Emby;
+using FluentAssertions;
+using Microsoft.Extensions.Logging;
+using Moq;
+using NUnit.Framework;
+
+namespace ErsatzTV.Core.Tests.Emby;
+
+[TestFixture]
+public class EmbyPathReplacementServiceTests
+{
+    [Test]
+    public async Task EmbyWindows_To_EtvWindows()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = @"C:\Something\Some Shared Folder",
+                LocalPath = @"C:\Something Else\Some Shared Folder",
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Windows" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetEmbyPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(true);
+
+        var service = new EmbyPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<EmbyPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"C:\Something\Some Shared Folder\Some Movie\Some Movie.mkv");
+
+        result.Should().Be(@"C:\Something Else\Some Shared Folder\Some Movie\Some Movie.mkv");
+    }
+
+    [Test]
+    public async Task EmbyWindows_To_EtvLinux()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = @"C:\Something\Some Shared Folder",
+                LocalPath = @"/mnt/something else/Some Shared Folder",
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Windows" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetEmbyPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new EmbyPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<EmbyPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"C:\Something\Some Shared Folder\Some Movie\Some Movie.mkv");
+
+        result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
+    }
+
+    [Test]
+    public async Task EmbyWindows_To_EtvLinux_UncPath()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = @"\\192.168.1.100\Something\Some Shared Folder",
+                LocalPath = @"/mnt/something else/Some Shared Folder",
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Windows" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetEmbyPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new EmbyPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<EmbyPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"\\192.168.1.100\Something\Some Shared Folder\Some Movie\Some Movie.mkv");
+
+        result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
+    }
+
+    [Test]
+    public async Task EmbyWindows_To_EtvLinux_UncPathWithTrailingSlash()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = @"\\192.168.1.100\Something\Some Shared Folder\",
+                LocalPath = @"/mnt/something else/Some Shared Folder/",
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Windows" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetEmbyPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new EmbyPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<EmbyPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"\\192.168.1.100\Something\Some Shared Folder\Some Movie\Some Movie.mkv");
+
+        result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
+    }
+
+    [Test]
+    public async Task EmbyLinux_To_EtvWindows()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = @"/mnt/something/Some Shared Folder",
+                LocalPath = @"C:\Something Else\Some Shared Folder",
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Linux" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetEmbyPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(true);
+
+        var service = new EmbyPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<EmbyPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+
+        result.Should().Be(@"C:\Something Else\Some Shared Folder\Some Movie\Some Movie.mkv");
+    }
+
+    [Test]
+    public async Task EmbyLinux_To_EtvLinux()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = @"/mnt/something/Some Shared Folder",
+                LocalPath = @"/mnt/something else/Some Shared Folder",
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Linux" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetEmbyPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new EmbyPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<EmbyPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+
+        result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
+    }
+    
+    [Test]
+    public async Task Should_Not_Throw_For_Null_EmbyPath()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = null,
+                LocalPath = @"/mnt/something else/Some Shared Folder",
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Linux" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetEmbyPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new EmbyPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<EmbyPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+
+        result.Should().Be(@"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+    }
+    
+    [Test]
+    public async Task Should_Not_Throw_For_Null_LocalPath()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = @"/mnt/something/Some Shared Folder",
+                LocalPath = null,
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Linux" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetEmbyPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new EmbyPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<EmbyPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+
+        result.Should().Be(@"/Some Movie/Some Movie.mkv");
+    }
+}
\ No newline at end of file
diff --git a/ErsatzTV.Core.Tests/Jellyfin/JellyfinPathReplacementServiceTests.cs b/ErsatzTV.Core.Tests/Jellyfin/JellyfinPathReplacementServiceTests.cs
index 3e61e914e..539bba537 100644
--- a/ErsatzTV.Core.Tests/Jellyfin/JellyfinPathReplacementServiceTests.cs
+++ b/ErsatzTV.Core.Tests/Jellyfin/JellyfinPathReplacementServiceTests.cs
@@ -204,4 +204,68 @@ public class JellyfinPathReplacementServiceTests
 
         result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
     }
+    
+    [Test]
+    public async Task Should_Not_Throw_For_Null_JellyfinPath()
+    {
+        var replacements = new List<JellyfinPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                JellyfinPath = null,
+                LocalPath = @"/mnt/something else/Some Shared Folder",
+                JellyfinMediaSource = new JellyfinMediaSource { OperatingSystem = "Linux" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetJellyfinPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new JellyfinPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<JellyfinPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementJellyfinPath(
+            0,
+            @"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+
+        result.Should().Be(@"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+    }
+    
+    [Test]
+    public async Task Should_Not_Throw_For_Null_LocalPath()
+    {
+        var replacements = new List<JellyfinPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                JellyfinPath = @"/mnt/something/Some Shared Folder",
+                LocalPath = null,
+                JellyfinMediaSource = new JellyfinMediaSource { OperatingSystem = "Linux" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetJellyfinPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new JellyfinPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<JellyfinPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementJellyfinPath(
+            0,
+            @"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+
+        result.Should().Be(@"/Some Movie/Some Movie.mkv");
+    }
 }
\ No newline at end of file
diff --git a/ErsatzTV.Core.Tests/Plex/PlexPathReplacementServiceTests.cs b/ErsatzTV.Core.Tests/Plex/PlexPathReplacementServiceTests.cs
index 582a4f8c4..dd2364685 100644
--- a/ErsatzTV.Core.Tests/Plex/PlexPathReplacementServiceTests.cs
+++ b/ErsatzTV.Core.Tests/Plex/PlexPathReplacementServiceTests.cs
@@ -204,4 +204,68 @@ public class PlexPathReplacementServiceTests
 
         result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
     }
+    
+    [Test]
+    public async Task Should_Not_Throw_For_Null_PlexPath()
+    {
+        var replacements = new List<PlexPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                PlexPath = null,
+                LocalPath = @"/mnt/something else/Some Shared Folder",
+                PlexMediaSource = new PlexMediaSource { Platform = "Linux" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetPlexPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new PlexPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<PlexPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementPlexPath(
+            0,
+            @"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+
+        result.Should().Be(@"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+    }
+    
+    [Test]
+    public async Task Should_Not_Throw_For_Null_LocalPath()
+    {
+        var replacements = new List<PlexPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                PlexPath = @"/mnt/something/Some Shared Folder",
+                LocalPath = null,
+                PlexMediaSource = new PlexMediaSource { Platform = "Linux" }
+            }
+        };
+
+        var repo = new Mock<IMediaSourceRepository>();
+        repo.Setup(x => x.GetPlexPathReplacementsByLibraryId(It.IsAny<int>())).Returns(replacements.AsTask());
+
+        var runtime = new Mock<IRuntimeInfo>();
+        runtime.Setup(x => x.IsOSPlatform(OSPlatform.Windows)).Returns(false);
+
+        var service = new PlexPathReplacementService(
+            repo.Object,
+            runtime.Object,
+            new Mock<ILogger<PlexPathReplacementService>>().Object);
+
+        string result = await service.GetReplacementPlexPath(
+            0,
+            @"/mnt/something/Some Shared Folder/Some Movie/Some Movie.mkv");
+
+        result.Should().Be(@"/Some Movie/Some Movie.mkv");
+    }
 }
\ No newline at end of file
diff --git a/ErsatzTV.Core/Emby/EmbyPathReplacementService.cs b/ErsatzTV.Core/Emby/EmbyPathReplacementService.cs
index 443725283..14539c914 100644
--- a/ErsatzTV.Core/Emby/EmbyPathReplacementService.cs
+++ b/ErsatzTV.Core/Emby/EmbyPathReplacementService.cs
@@ -40,6 +40,11 @@ public class EmbyPathReplacementService : IEmbyPathReplacementService
             .SingleOrDefault(
                 r =>
                 {
+                    if (string.IsNullOrWhiteSpace(r.EmbyPath))
+                    {
+                        return false;
+                    }
+
                     string separatorChar = IsWindows(r.EmbyMediaSource, path) ? @"\" : @"/";
                     string prefix = r.EmbyPath.EndsWith(separatorChar)
                         ? r.EmbyPath
@@ -47,32 +52,32 @@ public class EmbyPathReplacementService : IEmbyPathReplacementService
                     return path.StartsWith(prefix);
                 });
 
-        return maybeReplacement.Match(
-            replacement =>
+        foreach (EmbyPathReplacement replacement in maybeReplacement)
+        {
+            string finalPath = path.Replace(replacement.EmbyPath, replacement.LocalPath);
+            if (IsWindows(replacement.EmbyMediaSource, path) && !_runtimeInfo.IsOSPlatform(OSPlatform.Windows))
             {
-                string finalPath = path.Replace(replacement.EmbyPath, replacement.LocalPath);
-                if (IsWindows(replacement.EmbyMediaSource, path) && !_runtimeInfo.IsOSPlatform(OSPlatform.Windows))
-                {
-                    finalPath = finalPath.Replace(@"\", @"/");
-                }
-                else if (!IsWindows(replacement.EmbyMediaSource, path) &&
-                         _runtimeInfo.IsOSPlatform(OSPlatform.Windows))
-                {
-                    finalPath = finalPath.Replace(@"/", @"\");
-                }
+                finalPath = finalPath.Replace(@"\", @"/");
+            }
+            else if (!IsWindows(replacement.EmbyMediaSource, path) &&
+                     _runtimeInfo.IsOSPlatform(OSPlatform.Windows))
+            {
+                finalPath = finalPath.Replace(@"/", @"\");
+            }
 
-                if (log)
-                {
-                    _logger.LogInformation(
-                        "Replacing emby path {EmbyPath} with {LocalPath} resulting in {FinalPath}",
-                        replacement.EmbyPath,
-                        replacement.LocalPath,
-                        finalPath);
-                }
+            if (log)
+            {
+                _logger.LogInformation(
+                    "Replacing emby path {EmbyPath} with {LocalPath} resulting in {FinalPath}",
+                    replacement.EmbyPath,
+                    replacement.LocalPath,
+                    finalPath);
+            }
 
-                return finalPath;
-            },
-            () => path);
+            return finalPath;
+        }
+
+        return path;
     }
 
     private static bool IsWindows(EmbyMediaSource embyMediaSource, string path)
diff --git a/ErsatzTV.Core/Jellyfin/JellyfinPathReplacementService.cs b/ErsatzTV.Core/Jellyfin/JellyfinPathReplacementService.cs
index b1cca0dbb..0c5480e61 100644
--- a/ErsatzTV.Core/Jellyfin/JellyfinPathReplacementService.cs
+++ b/ErsatzTV.Core/Jellyfin/JellyfinPathReplacementService.cs
@@ -40,6 +40,11 @@ public class JellyfinPathReplacementService : IJellyfinPathReplacementService
             .SingleOrDefault(
                 r =>
                 {
+                    if (string.IsNullOrWhiteSpace(r.JellyfinPath))
+                    {
+                        return false;
+                    }
+
                     string separatorChar = IsWindows(r.JellyfinMediaSource, path) ? @"\" : @"/";
                     string prefix = r.JellyfinPath.EndsWith(separatorChar)
                         ? r.JellyfinPath
@@ -47,33 +52,33 @@ public class JellyfinPathReplacementService : IJellyfinPathReplacementService
                     return path.StartsWith(prefix);
                 });
 
-        return maybeReplacement.Match(
-            replacement =>
+        foreach (JellyfinPathReplacement replacement in maybeReplacement)
+        {
+            string finalPath = path.Replace(replacement.JellyfinPath, replacement.LocalPath);
+            if (IsWindows(replacement.JellyfinMediaSource, path) &&
+                !_runtimeInfo.IsOSPlatform(OSPlatform.Windows))
             {
-                string finalPath = path.Replace(replacement.JellyfinPath, replacement.LocalPath);
-                if (IsWindows(replacement.JellyfinMediaSource, path) &&
-                    !_runtimeInfo.IsOSPlatform(OSPlatform.Windows))
-                {
-                    finalPath = finalPath.Replace(@"\", @"/");
-                }
-                else if (!IsWindows(replacement.JellyfinMediaSource, path) &&
-                         _runtimeInfo.IsOSPlatform(OSPlatform.Windows))
-                {
-                    finalPath = finalPath.Replace(@"/", @"\");
-                }
+                finalPath = finalPath.Replace(@"\", @"/");
+            }
+            else if (!IsWindows(replacement.JellyfinMediaSource, path) &&
+                     _runtimeInfo.IsOSPlatform(OSPlatform.Windows))
+            {
+                finalPath = finalPath.Replace(@"/", @"\");
+            }
 
-                if (log)
-                {
-                    _logger.LogInformation(
-                        "Replacing jellyfin path {JellyfinPath} with {LocalPath} resulting in {FinalPath}",
-                        replacement.JellyfinPath,
-                        replacement.LocalPath,
-                        finalPath);
-                }
+            if (log)
+            {
+                _logger.LogInformation(
+                    "Replacing jellyfin path {JellyfinPath} with {LocalPath} resulting in {FinalPath}",
+                    replacement.JellyfinPath,
+                    replacement.LocalPath,
+                    finalPath);
+            }
 
-                return finalPath;
-            },
-            () => path);
+            return finalPath;
+        }
+
+        return path;
     }
 
     private static bool IsWindows(JellyfinMediaSource jellyfinMediaSource, string path)
diff --git a/ErsatzTV.Core/Plex/PlexPathReplacementService.cs b/ErsatzTV.Core/Plex/PlexPathReplacementService.cs
index 9dbce8c95..6be69c8e8 100644
--- a/ErsatzTV.Core/Plex/PlexPathReplacementService.cs
+++ b/ErsatzTV.Core/Plex/PlexPathReplacementService.cs
@@ -37,36 +37,41 @@ public class PlexPathReplacementService : IPlexPathReplacementService
             .SingleOrDefault(
                 r =>
                 {
+                    if (string.IsNullOrWhiteSpace(r.PlexPath))
+                    {
+                        return false;
+                    }
+
                     string separatorChar = IsWindows(r.PlexMediaSource) ? @"\" : @"/";
                     string prefix = r.PlexPath.EndsWith(separatorChar) ? r.PlexPath : r.PlexPath + separatorChar;
                     return path.StartsWith(prefix);
                 });
 
-        return maybeReplacement.Match(
-            replacement =>
+        foreach (PlexPathReplacement replacement in maybeReplacement)
+        {
+            string finalPath = path.Replace(replacement.PlexPath, replacement.LocalPath);
+            if (IsWindows(replacement.PlexMediaSource) && !_runtimeInfo.IsOSPlatform(OSPlatform.Windows))
             {
-                string finalPath = path.Replace(replacement.PlexPath, replacement.LocalPath);
-                if (IsWindows(replacement.PlexMediaSource) && !_runtimeInfo.IsOSPlatform(OSPlatform.Windows))
-                {
-                    finalPath = finalPath.Replace(@"\", @"/");
-                }
-                else if (!IsWindows(replacement.PlexMediaSource) && _runtimeInfo.IsOSPlatform(OSPlatform.Windows))
-                {
-                    finalPath = finalPath.Replace(@"/", @"\");
-                }
+                finalPath = finalPath.Replace(@"\", @"/");
+            }
+            else if (!IsWindows(replacement.PlexMediaSource) && _runtimeInfo.IsOSPlatform(OSPlatform.Windows))
+            {
+                finalPath = finalPath.Replace(@"/", @"\");
+            }
 
-                if (log)
-                {
-                    _logger.LogInformation(
-                        "Replacing plex path {PlexPath} with {LocalPath} resulting in {FinalPath}",
-                        replacement.PlexPath,
-                        replacement.LocalPath,
-                        finalPath);
-                }
+            if (log)
+            {
+                _logger.LogInformation(
+                    "Replacing plex path {PlexPath} with {LocalPath} resulting in {FinalPath}",
+                    replacement.PlexPath,
+                    replacement.LocalPath,
+                    finalPath);
+            }
 
-                return finalPath;
-            },
-            () => path);
+            return finalPath;
+        }
+
+        return path;
     }
 
     private static bool IsWindows(PlexMediaSource plexMediaSource) =>