diff --git a/CHANGELOG.md b/CHANGELOG.md
index 530683996..9aca1acfc 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -48,6 +48,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 - Fix AV1 software decoder priority (`libdav1d`, `libaom-av1`, `av1`)
 - Fix some stream failures caused by loudnorm filter
 - Fix multi-collection editor improperly disabling collections/smart collections that haven't already been added to the multi-collection
+- Fix path replacement logic when media server paths use inconsistent casing (e.g. `\\SERVERNAME` AND `\\ServerName`)
 
 ### Changed
 - Log search index updates under scanner category at debug level, to indicate a potential cause for the UI being out of date
diff --git a/ErsatzTV.Core.Tests/Emby/EmbyPathReplacementServiceTests.cs b/ErsatzTV.Core.Tests/Emby/EmbyPathReplacementServiceTests.cs
index 6835c4b2d..0e8f37daa 100644
--- a/ErsatzTV.Core.Tests/Emby/EmbyPathReplacementServiceTests.cs
+++ b/ErsatzTV.Core.Tests/Emby/EmbyPathReplacementServiceTests.cs
@@ -164,6 +164,38 @@ public class EmbyPathReplacementServiceTests
 
         result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
     }
+    
+    [Test]
+    public async Task EmbyWindows_To_EtvLinux_UncPathWithMixedCaseServerName()
+    {
+        var replacements = new List<EmbyPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                EmbyPath = @"\\ServerName\Something\Some Shared Folder\",
+                LocalPath = @"/mnt/something else/Some Shared Folder/",
+                EmbyMediaSource = new EmbyMediaSource { OperatingSystem = "Windows" }
+            }
+        };
+
+        IMediaSourceRepository repo = Substitute.For<IMediaSourceRepository>();
+        repo.GetEmbyPathReplacementsByLibraryId(Arg.Any<int>()).Returns(replacements.AsTask());
+
+        IRuntimeInfo runtime = Substitute.For<IRuntimeInfo>();
+        runtime.IsOSPlatform(OSPlatform.Windows).Returns(false);
+
+        var service = new EmbyPathReplacementService(
+            repo,
+            runtime,
+            Substitute.For<ILogger<EmbyPathReplacementService>>());
+
+        string result = await service.GetReplacementEmbyPath(
+            0,
+            @"\\SERVERNAME\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()
diff --git a/ErsatzTV.Core.Tests/Jellyfin/JellyfinPathReplacementServiceTests.cs b/ErsatzTV.Core.Tests/Jellyfin/JellyfinPathReplacementServiceTests.cs
index 9a1ffd59f..6adc621ac 100644
--- a/ErsatzTV.Core.Tests/Jellyfin/JellyfinPathReplacementServiceTests.cs
+++ b/ErsatzTV.Core.Tests/Jellyfin/JellyfinPathReplacementServiceTests.cs
@@ -164,6 +164,38 @@ public class JellyfinPathReplacementServiceTests
 
         result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
     }
+    
+    [Test]
+    public async Task JellyfinWindows_To_EtvLinux_UncPathWithMixedCaseServerName()
+    {
+        var replacements = new List<JellyfinPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                JellyfinPath = @"\\ServerName\Something\Some Shared Folder\",
+                LocalPath = @"/mnt/something else/Some Shared Folder/",
+                JellyfinMediaSource = new JellyfinMediaSource { OperatingSystem = "Windows" }
+            }
+        };
+
+        IMediaSourceRepository repo = Substitute.For<IMediaSourceRepository>();
+        repo.GetJellyfinPathReplacementsByLibraryId(Arg.Any<int>()).Returns(replacements.AsTask());
+
+        IRuntimeInfo runtime = Substitute.For<IRuntimeInfo>();
+        runtime.IsOSPlatform(OSPlatform.Windows).Returns(false);
+
+        var service = new JellyfinPathReplacementService(
+            repo,
+            runtime,
+            Substitute.For<ILogger<JellyfinPathReplacementService>>());
+
+        string result = await service.GetReplacementJellyfinPath(
+            0,
+            @"\\SERVERNAME\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 JellyfinLinux_To_EtvWindows()
diff --git a/ErsatzTV.Core.Tests/Plex/PlexPathReplacementServiceTests.cs b/ErsatzTV.Core.Tests/Plex/PlexPathReplacementServiceTests.cs
index 06d436cdd..f0ed6686c 100644
--- a/ErsatzTV.Core.Tests/Plex/PlexPathReplacementServiceTests.cs
+++ b/ErsatzTV.Core.Tests/Plex/PlexPathReplacementServiceTests.cs
@@ -140,6 +140,38 @@ public class PlexPathReplacementServiceTests
 
         result.Should().Be(@"/mnt/something else/Some Shared Folder/Some Movie/Some Movie.mkv");
     }
+    
+    [Test]
+    public async Task PlexWindows_To_EtvLinux_UncPathWithMixedCaseServerName()
+    {
+        var replacements = new List<PlexPathReplacement>
+        {
+            new()
+            {
+                Id = 1,
+                PlexPath = @"\\ServerName\Something\Some Shared Folder\",
+                LocalPath = @"/mnt/something else/Some Shared Folder/",
+                PlexMediaSource = new PlexMediaSource { Platform = "Windows" }
+            }
+        };
+
+        IMediaSourceRepository repo = Substitute.For<IMediaSourceRepository>();
+        repo.GetPlexPathReplacementsByLibraryId(Arg.Any<int>()).Returns(replacements.AsTask());
+
+        IRuntimeInfo runtime = Substitute.For<IRuntimeInfo>();
+        runtime.IsOSPlatform(OSPlatform.Windows).Returns(false);
+
+        var service = new PlexPathReplacementService(
+            repo,
+            runtime,
+            Substitute.For<ILogger<PlexPathReplacementService>>());
+
+        string result = await service.GetReplacementPlexPath(
+            0,
+            @"\\SERVERNAME\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 PlexLinux_To_EtvWindows()
diff --git a/ErsatzTV.Core/Emby/EmbyPathReplacementService.cs b/ErsatzTV.Core/Emby/EmbyPathReplacementService.cs
index 6be92fec4..50601b172 100644
--- a/ErsatzTV.Core/Emby/EmbyPathReplacementService.cs
+++ b/ErsatzTV.Core/Emby/EmbyPathReplacementService.cs
@@ -1,4 +1,5 @@
 using System.Runtime.InteropServices;
+using System.Text.RegularExpressions;
 using ErsatzTV.Core.Domain;
 using ErsatzTV.Core.Interfaces.Emby;
 using ErsatzTV.Core.Interfaces.Repositories;
@@ -85,7 +86,10 @@ public class EmbyPathReplacementService : IEmbyPathReplacementService
 
         foreach (EmbyPathReplacement replacement in maybeReplacement)
         {
-            string finalPath = path.Replace(replacement.EmbyPath, replacement.LocalPath);
+            string finalPath = Regex.Replace(path,
+                Regex.Escape(replacement.EmbyPath),
+                Regex.Replace(replacement.LocalPath ?? string.Empty, "\\$[0-9]+", @"$$$0"),
+                RegexOptions.IgnoreCase);
             if (IsWindows(replacement.EmbyMediaSource, path) && !isTargetPlatformWindows)
             {
                 finalPath = finalPath.Replace(@"\", @"/");
diff --git a/ErsatzTV.Core/Jellyfin/JellyfinPathReplacementService.cs b/ErsatzTV.Core/Jellyfin/JellyfinPathReplacementService.cs
index 6bb6ae521..948ac12e5 100644
--- a/ErsatzTV.Core/Jellyfin/JellyfinPathReplacementService.cs
+++ b/ErsatzTV.Core/Jellyfin/JellyfinPathReplacementService.cs
@@ -1,4 +1,5 @@
 using System.Runtime.InteropServices;
+using System.Text.RegularExpressions;
 using ErsatzTV.Core.Domain;
 using ErsatzTV.Core.Interfaces.Jellyfin;
 using ErsatzTV.Core.Interfaces.Repositories;
@@ -85,7 +86,10 @@ public class JellyfinPathReplacementService : IJellyfinPathReplacementService
 
         foreach (JellyfinPathReplacement replacement in maybeReplacement)
         {
-            string finalPath = path.Replace(replacement.JellyfinPath, replacement.LocalPath);
+            string finalPath = Regex.Replace(path,
+                Regex.Escape(replacement.JellyfinPath),
+                Regex.Replace(replacement.LocalPath ?? string.Empty, "\\$[0-9]+", @"$$$0"),
+                RegexOptions.IgnoreCase);
             if (IsWindows(replacement.JellyfinMediaSource, path) && !isTargetPlatformWindows)
             {
                 finalPath = finalPath.Replace(@"\", @"/");
diff --git a/ErsatzTV.Core/Plex/PlexPathReplacementService.cs b/ErsatzTV.Core/Plex/PlexPathReplacementService.cs
index 2bc3d2bb6..2e263ad74 100644
--- a/ErsatzTV.Core/Plex/PlexPathReplacementService.cs
+++ b/ErsatzTV.Core/Plex/PlexPathReplacementService.cs
@@ -1,4 +1,5 @@
 using System.Runtime.InteropServices;
+using System.Text.RegularExpressions;
 using ErsatzTV.Core.Domain;
 using ErsatzTV.Core.Interfaces.Plex;
 using ErsatzTV.Core.Interfaces.Repositories;
@@ -51,7 +52,10 @@ public class PlexPathReplacementService : IPlexPathReplacementService
 
         foreach (PlexPathReplacement replacement in maybeReplacement)
         {
-            string finalPath = path.Replace(replacement.PlexPath, replacement.LocalPath);
+            string finalPath = Regex.Replace(path,
+                Regex.Escape(replacement.PlexPath),
+                Regex.Replace(replacement.LocalPath ?? string.Empty, "\\$[0-9]+", @"$$$0"),
+                RegexOptions.IgnoreCase);
             if (IsWindows(replacement.PlexMediaSource) && !_runtimeInfo.IsOSPlatform(OSPlatform.Windows))
             {
                 finalPath = finalPath.Replace(@"\", @"/");