diff --git a/src/SMAPI/Framework/ContentManagers/ModContentManager.cs b/src/SMAPI/Framework/ContentManagers/ModContentManager.cs
index f11ce9648..52287445a 100644
--- a/src/SMAPI/Framework/ContentManagers/ModContentManager.cs
+++ b/src/SMAPI/Framework/ContentManagers/ModContentManager.cs
@@ -30,6 +30,9 @@ internal sealed class ModContentManager : BaseContentManager
     /*********
     ** Fields
     *********/
+    /// <summary>A path segment which navigates to the parent directory.</summary>
+    private const string DirectoryClimbingPathSegment = "..";
+
     /// <summary>Encapsulates SMAPI's JSON file parsing.</summary>
     private readonly JsonHelper JsonHelper;
 
@@ -399,28 +402,41 @@ private void FixTilesheetPaths(Map map, string relativeMapPath, bool fixEagerPat
         this.Monitor.VerboseLog($"Fixing tilesheet paths for map '{relativeMapPath}' from mod '{this.ModName}'...");
         foreach (TileSheet tilesheet in map.TileSheets)
         {
-            // get image source
+            // get image path
             tilesheet.ImageSource = this.NormalizePathSeparators(tilesheet.ImageSource);
             string imageSource = tilesheet.ImageSource;
+            if (fixEagerPathPrefixes && relativeMapFolder.Length > 0 && imageSource?.StartsWith(relativeMapFolder) is true)
+                imageSource = imageSource[(relativeMapFolder.Length + 1)..];
 
-            // validate image source
+            // ensure path isn't empty
             if (string.IsNullOrWhiteSpace(imageSource))
                 throw new SContentLoadException(ContentLoadErrorType.InvalidData, $"{this.ModName} loaded map '{relativeMapPath}' with invalid tilesheet '{tilesheet.Id}'. This tilesheet has no image source.");
 
-            // reverse incorrect eager tilesheet path prefixing
-            if (fixEagerPathPrefixes && relativeMapFolder.Length > 0 && imageSource.StartsWith(relativeMapFolder))
-                imageSource = imageSource[(relativeMapFolder.Length + 1)..];
+            // ensure path is relative
+            if (Path.IsPathRooted(imageSource))
+                throw this.GetPathError(relativeMapFolder, imageSource, $"Tilesheet paths must not be an absolute path ({Path.GetPathRoot(imageSource)}).");
 
-            // validate tilesheet path
-            string errorPrefix = $"{this.ModName} loaded map '{relativeMapPath}' with invalid tilesheet path '{imageSource}'.";
-            if (Path.IsPathRooted(imageSource) || PathUtilities.GetSegments(imageSource).Contains(".."))
-                throw new SContentLoadException(ContentLoadErrorType.InvalidData, $"{errorPrefix} Tilesheet paths must be a relative path without directory climbing (../).");
+            // ensure any directory climbing is valid
+            // Tilesheet paths are relative to either the `Content/Maps` folder or the map file. Directory climbing is
+            // restricted for safety and simplicity:
+            //   1. Can only climb at the start of the path (e.g. `../LooseSprites/Cursors` but not `Mines/../Barn`).
+            //   2. Can only climb once (to avoid escaping the `Content` folder).
+            //   3. Always relative to the `Content/Maps` folder (not the map file).
+            {
+                const string climbSegment = ModContentManager.DirectoryClimbingPathSegment;
+                string[] pathSegments = PathUtilities.GetSegments(imageSource);
+                if (pathSegments.Contains(climbSegment))
+                {
+                    if (pathSegments[0] != climbSegment || pathSegments.Count(segment => segment == climbSegment) > 1)
+                        throw this.GetPathError(relativeMapFolder, imageSource, $"Directory climbing ({climbSegment}/) is only permitted once at the start of the path.");
+                }
+            }
 
             // load best match
             try
             {
                 if (!this.TryGetTilesheetAssetName(relativeMapFolder, imageSource, out IAssetName? assetName, out string? error))
-                    throw new SContentLoadException(ContentLoadErrorType.InvalidData, $"{errorPrefix} {error}");
+                    throw this.GetPathError(relativeMapFolder, imageSource, error);
 
                 if (assetName is not null)
                 {
@@ -435,7 +451,7 @@ private void FixTilesheetPaths(Map map, string relativeMapPath, bool fixEagerPat
                 if (ex is SContentLoadException)
                     throw;
 
-                throw new SContentLoadException(ContentLoadErrorType.InvalidData, $"{errorPrefix} The tilesheet couldn't be loaded.", ex);
+                throw this.GetPathError(relativeMapFolder, imageSource, "The tilesheet couldn't be loaded.", ex);
             }
         }
     }
@@ -444,10 +460,10 @@ private void FixTilesheetPaths(Map map, string relativeMapPath, bool fixEagerPat
     /// <param name="modRelativeMapFolder">The folder path containing the map, relative to the mod folder.</param>
     /// <param name="relativePath">The tilesheet path to load.</param>
     /// <param name="assetName">The found asset name.</param>
-    /// <param name="error">A message indicating why the file couldn't be loaded.</param>
+    /// <param name="error">A message indicating why the file couldn't be loaded, if applicable.</param>
     /// <returns>Returns whether the asset name was found.</returns>
     /// <remarks>See remarks on <see cref="FixTilesheetPaths"/>.</remarks>
-    private bool TryGetTilesheetAssetName(string modRelativeMapFolder, string relativePath, out IAssetName? assetName, out string? error)
+    private bool TryGetTilesheetAssetName(string modRelativeMapFolder, string relativePath, out IAssetName? assetName, [NotNullWhen(false)] out string? error)
     {
         error = null;
 
@@ -467,7 +483,9 @@ private bool TryGetTilesheetAssetName(string modRelativeMapFolder, string relati
                 relativePath = Path.Combine(Path.GetDirectoryName(relativePath) ?? "", filename.TrimStart('.'));
         }
 
-        // get relative to map file
+        // get relative to map file unless path has directory climbing
+        const string climbSegment = ModContentManager.DirectoryClimbingPathSegment;
+        if (!relativePath.StartsWith(climbSegment) && PathUtilities.GetSegments(relativePath, 2)[0] != climbSegment) // directory climbing can only be at the start of the path
         {
             string localKey = Path.Combine(modRelativeMapFolder, relativePath);
             if (this.GetModFile<Texture2D>(localKey).Exists)
@@ -522,11 +540,17 @@ private bool GetContentFolderFileExists(string key)
     private string GetContentKeyForTilesheetImageSource(string relativePath)
     {
         string key = relativePath;
-        string topFolder = PathUtilities.GetSegments(key, limit: 2)[0];
 
-        // convert image source relative to map file into asset key
-        if (!topFolder.Equals("Maps", StringComparison.OrdinalIgnoreCase))
-            key = Path.Combine("Maps", key);
+        // make path relative to Content folder
+        {
+            string topFolder = PathUtilities.GetSegments(key, limit: 2)[0];
+            const string climbSegment = ModContentManager.DirectoryClimbingPathSegment;
+
+            if (topFolder == climbSegment)
+                key = key[(climbSegment.Length + 1)..];
+            else if (!topFolder.Equals("Maps", StringComparison.OrdinalIgnoreCase))
+                key = Path.Combine("Maps", key);
+        }
 
         // remove file extension from unpacked file
         if (key.EndsWith(".png", StringComparison.OrdinalIgnoreCase))
@@ -534,4 +558,14 @@ private string GetContentKeyForTilesheetImageSource(string relativePath)
 
         return key;
     }
+
+    /// <summary>Get an exception indicating that a map asset can't be loaded because one of its tilesheets has an invalid path.</summary>
+    /// <param name="relativeMapPath">The relative path to the folder which contains the map asset, relative to the mod folder.</param>
+    /// <param name="imageSource">The tilesheet's path to the image file.</param>
+    /// <param name="error">The error message indicating why loading it failed. (Basic metadata like the image source is prepended automatically.)</param>
+    /// <param name="ex">The inner exception which caused the error, if applicable.</param>
+    private SContentLoadException GetPathError(string relativeMapPath, string imageSource, string error, Exception? ex = null)
+    {
+        return new SContentLoadException(ContentLoadErrorType.InvalidData, $"{this.ModName} loaded map '{relativeMapPath}' with invalid tilesheet path '{imageSource}'. {error}", ex);
+    }
 }